bluuebunny/crossref_metadata_2025 huggingface dataset:
Derivatives of benzo[4,5]cyclohepta[1,2‐b]thiophene. 4. Synthesis of 1‐(9,10‐dihydro‐4H‐benzo[4,5]cyclohepta[1,2‐b]thiophen‐4‐yl)‐3‐alkylaminoazetidines
Authors: Jiménez Amelia , Vega Salvador
Published: March 2009

Thirteen 1‐(9,10‐dihydro‐4H‐benzo[4,5]cyclohepta[1,2‐b]thiophen‐4‐yl)‐3‐alkylaminoazetidines 11 have been synthesized in three steps from 4‐amino‐9,10‐dihydro‐4H‐benzo[4,5]cyclohepta[1,2‐b]thiophene (6), which was obtained from the reduction of either 4‐azido 4 or 4‐hydroxyimino 5 derivatives. All the compounds have been evaluated as potential antidepressive agents.
Reaction of 6‐ethylamino‐3‐methyluracil with nitrobenzenes
Authors: Harayama Takashi , Jinno Hideto , Tezuka Yasuhiro , Yoneda Fumio
Published: March 2009

Reaction of 6‐ethylamino‐3‐methyluracil (1) with nitrobenzenes in hexamethylphosphoric triamide gave isoalloxazines in 3.8–18 percent yield. In the presence of potassium carbonate, reaction of 1 with o‐fluoronitrobenzene afforded 5‐substituted uracil 3 in moderate yield.
Synthesis of novel furan and thiophene PAH'S related to acephenanthrylene
Authors: Lee‐Ruff Edward , Chung Ying‐Sheng
Published: March 2009

The total syntheses of furan and thiophene PAH's related to acephenanthrylene are reported. Cyclobutanones which were obtained by [2 + 2] addition of ketenes with 2,3‐dihydrofuran or 2,3‐dihydrothiophene regioselectively could be converted into angular PAH skeleton molecules by rearrangements with polyphosphoric acid. 2,3‐Dichloro‐5,6‐dicyanobenzoquinone was applied for aromatization to achieve the formation of PAH's.
Pyrrolopyridine analogs of nalidixic acid. 2. Pyrrolo[3,4–6]pyridines
Authors: Toja Emilio , Kettenring Jurgen , Goldstein Beth , Tarzia Giorgio
Published: March 2009

The synthesis of the new 1‐ethyl‐5,6‐dimethyl‐7‐(4‐methyl‐1‐piperazinyl)‐1,4‐dihydro‐4‐oxo‐1H‐pyrrolo[3,4‐b] pyridine‐3‐carboxylic acid (12) was carried out using ethyl 4‐amino‐2‐methyipyrrole‐3‐carboxylate as the starting material. Compound 12 was devoid of antibacterial activity in vitro.
The synthesis of two monosubstituted meso‐tetraphenylporphine sulfonates
Authors: Sun Yizhen , Martell Arthur E. , Chen Dian , Macfarlane Ronald D. , Mcneal Catherine J.
Published: March 2009

This paper describes the synthesis and characterization of two novel meso‐tetrakis(4‐sulfophenyl)‐21H,‐23H‐porphine (TPPS4) derivatives in which one of the phenyl rings is substituted with an anticancer agent. Several advantages of monosubstitution are pointed out: the higher efficiency of synthetic steps involving the derivatization of one, rather than several, functional group per porphyrin molecule, and the greater solubility and ease of purification of monosubstituted tetraphenylporphines. The new compounds have 5‐fluorouracil and cis dichloroethylenediamineplatinum (cis‐platinum) substituted in the meta positions of one of the phenyl rings in TPPS4. The palladium analog of the cis‐platinum dervative which contains two Pd(II) atoms per molecule ‐ one coordinated with the ethylenediamine moiety, and the other coordinated at the center of the porphyrin ring, was also prepared.
The synthesis of dimethoxy[1]benzothieno[2,3‐c]quinolines
Authors: Pakray Sudabeh , Castle Raymond N.
Published: March 2009

A series of dimethoxy[1]benzothieno[2,3‐c]quinolines have been prepared by photocyclization of the appropriate N‐phenyl‐3‐chlorobenzo[b]thiophene‐2‐carboxamides. The lactams obtained were converted into the thiolactams and their S‐methyl derivatives. The lactams were also converted into the corresponding chloro derivatives which were catalytically dechlorinated into the dimethoxy[1]benzothieno[2,3‐c]quinolines. The latter compounds were converted into the N‐methyl quaternary salts.
Synthesis of heterocyclic compounds. LI. Schiff bases of ethyl 2‐aminofurancarboxylates
Authors: Ciller J. A. , Seoane C. , Soto J. L. , Yruretagoyena B.
Published: March 2009

Diaryl‐ and Alkylaryl‐substituted 2‐aminofurancarboxylates have been obtained as Schiff bases 5,6 by cyclization of 2‐ethoxycarbonyl‐4‐oxonitriles 3,4; which result from hydrogen cyanide addition to ethyl α‐acylcinnamates 1,2.
Synthesis of some isomeric 4,11‐dihydro‐5H‐[1]benzoxocino[4,3‐d] or [3,4‐c]isoxazol‐5‐ones and isomeric 4,5,10,11‐tetrahydrobenzo[5,6]‐cycloocta[2,1‐d] or [1,2‐c]isoxazol‐5‐ones
Authors: Deshayes Christian , Chabannet Michel , Gelin Suzanne
Published: March 2009

The title compounds were prepared by acid‐catalyzed cyclization of aryloxymethyl‐ or (2‐arylethyl)‐4‐carboxymethylisoxazoles which in turn were synthesized from aryloxymethyl‐ or (2‐arylethyl)isoxazole‐4‐carboxylic acids by Arndt‐Eistert homologation.
Synthesis and stereochemistry of tetrahydroprotoberberine derivatives
Authors: Badia D. , Domínguez E. , Iriondo C.
Published: March 2009

A series of 5‐hydroxytetrahydroprotoberberines has been prepared from 3‐aryltetrahydroisoquinoline derivatives via successive N‐alkylation, oxidation and cyclization in acidic media. The relative configurations of the resulting diastereomeric 5‐hydroxytetrahydroprotoberberines are reported.
Electroorganic synthesis. Reductive alkylation of functionalized 1,2‐dithiole‐3‐thiones
Authors: Darchen André , Berthelot Pascal , Vaccher Claude , Viana M. Nazareth , Debaert Michel , Burgot Jean Louis
Published: March 2009

Two‐electron reduction of some substituted 1,2‐dithiole‐3‐thiones 1 followed by alkylation of the dianionic intermediates leads through electrosynthesis to mixture of Z and E isomers of the corresponding substituted alkyl‐(3‐thioalkyl)‐2‐propenedithioates 2, 3 in satisfactory yield. The structure of those products was established by 13C and 1H nmr and mass spectroscopy. The isomers ratios were determined by nmr spectroscopy.
Synthesis of 4‐(2‐acetoxyethoxymethyl)‐6‐methyl‐1,2,4‐triazin‐3(4H)‐one 1‐oxide as thymidine analogue
Authors: Banijamali Ali R. , Foye William O.
Published: March 2009

Alkylation of the sodium salt and the trimethyl silylated derivatives of 6‐methyl‐1,2,4‐triazin‐3(4H)‐one 1‐oxide with chloromethoxyethyl acetate, n‐hexyl chloride and benzyl bromide gave the 4‐substituted products. However, attempts to achieve the ring closure of N4‐(2‐acetoxyethoxymethyl)thiosemicarbazide with bicarbonyl compounds to the corresponding as‐triazines under different reaction conditions was not possible without disruption of the acetoxyethoxymethyl moiety. Although the as‐triazine nucleoside analog II did not show antileukemic activity, this and other 4‐alkylated as‐triazine 1‐oxides revealed good growth inhibitory effects against a representative spectrum of microorganisms.
Synthesis of 5‐phenylnaphtho[1,2‐b]benzofuran by ambident alkylation of 1‐naphthol
Authors: Campaigne E. , Weddleton Richard F.
Published: March 2009

Reaction of 1‐naphthol with 2‐chlorocyclohexanone in alkaline alcohol gave as the major product 5‐(2′‐oxocyclohexyl)‐7,8,9,10‐tetrahydronaphtho[1,2‐b]benzofuran (1), which could be converted to the title compound 5 by reduction and dehydrogenation. This product arises from ambident alkylation of 1‐naphthol at the 2‐and 4‐positions. Via the 2′‐oxocyclohexyl ether, 5 was also synthesized from 4‐phenyl‐1‐naphthol.
Synthesis of 3‐(2‐benzothiazolylthio)propanenitrile and related products
Authors: D'Amico John J. , Suba Lydia , Ruminski Peter G.
Published: March 2009

The reaction of 2‐mercaptobenzothiazole, 2‐mercaptobenzoxazole or 5‐chloro‐2‐mercaptobenzothiazole with either acrylonitrile or acrylamide under basic conditions afforded the N‐cyanoethylated products 1, 2 and 3 or the N‐amidoethylated products 4, 5 and 6, respectively. The reaction of the sodium salts of the same thiazolethiols with 3‐chloropropionitrile furnished a mixture containing the N‐cyanoethylated products 1, 2 and 3 and the unknown S‐cyanoethylated products 7, 8 and 9, respectively. Whereas, substituting 3‐chloropropionamide for 3‐ chloropropionitrile in the same reaction gave only the S‐substituted products 10, 11, and 12, respectively. The treatment of 10, 11 or 12 with phosphorus oxychloride or thionyl chloride in DMF afforded 7, 8 and 9 in excellent yields. Possible mechanisms and supporting nmr data are discussed.
Synthesis of variants of 5‐benzylacyclouridine and 5‐benzyloxybenzylacyclouridine
Authors: Chu Shih‐Hsi , Chen Zhi‐Hao , Weng Zum‐Yao , Rowe Elizabeth C. , Chu Edward , Chu Ming‐Yu Wang
Published: March 2009

A number of variations and derivatives of BAU (5‐benzylacyclouridine) and BBAU (5‐benzyloxybenzylacy‐clouridine), potent inhibitors of uridine phosphorylase were synthesized for evaluation as potential cancer chemotherapeutic agents. (“Acyclo” = 2′‐hydroxymethoxymethyl‐). These included a modification of the methylene group at N‐1, esters of the terminal hydroxyl of the acyclo group, and extension of the benzyl chain at position 5 of the uracil base. BBBAU was a very good potentiator of FUdR in cell culture.
Reactivity of 3H‐pyrimido[5,4‐c] [1,2,5]oxadiazin‐3‐one towards carbanions: Synthesis of pteridine‐2,4‐diones
Authors: Giori P. , Poli T. , Veronese A. C. , Vicentini C. B. , Manfrini M. , Guarneri M.
Published: March 2009

The reaction of 3H‐pyrimido[5,4‐c] [1,2,5]oxadiazin‐3‐one (5) with carbanions prepared in situ from compounds containing an activated methylene group afforded 6,7‐disubstituted pteridine‐2,4‐diones 7a‐m in good yields. The reaction mechanism, involving the initial attack by carbanion at oxadiazinone nitrogen atom bonded to oxygen, is proposed and discussed.
Polycyclic N‐hetero compounds. XXVII. Synthesis and investigation of the antidepressive activity of a B‐Homo‐11,13,15‐triazasteroid and its related compoundsd
Authors: Hirota Takashi , Ieno Katsuhiro , Sasaki Kenji
Published: March 2009

A synthesis of 1,2,5,6‐tetrahydro‐4H‐benzo[3,4]cyclohepta[1,2‐e]imidazo[1,2‐c]pyrimidine (XII) having a novel ring system is described. Antidepressive activity of XII and its precursors VII‐X was screened by inhibitory action of reserpine‐induced hypothermia.
Intramolecular sulphonyl‐amidomethylation. Part I. Cyclization of benzylsulphonamides
Authors: Orazi Orfeo O. , Corral Renée A. , Bravo Rodolfo
Published: March 2009

Cyclization of benzylsulphonamides with aldehydes in strong acid media is a synthetically useful route to 3,4‐dihydro‐1H‐2,3‐benzothiazine 2,2‐dioxides III. With insufficient acid strength or reaction time, kinetic products IV and VI are obtained; the latter compounds can be converted into the thermodynamic products III under stronger conditions. The reactions proceed via imine VII or iminium VIII compounds as common intermediates.
A convenient preparation of 1,4‐dihydro‐1‐methyl‐4‐oxo‐2‐quinolinecarboxaldehyde from N‐methylisatoic anhydride
Authors: Coppola Gary M.
Published: March 2009

The dianion of hydroxyacetone is readily generated with LDA in THF at ‐65°. This dianion reacts rapidly with N‐methylisatoic anhydride (6) at ‐65° to furnish 2‐hydroxymethyl‐1‐methylquinolin‐4(1H)‐one (12). The alcohol is oxidized to aldehyde 4 with manganese dioxide, and is subsequently converted to α,β‐unsaturated ester 5 under Horner‐Emmons conditions.
Synthesis, 13C‐NMR characterization and antimicrobial properties of a novel series of 3‐(N‐Substituted thiocarbamoyl)hydrazino‐1,2,4‐triazino‐[5,6‐b]indole derivatives
Authors: Omar A.‐Mohsen M. E. , Eshba Nabil H. , Aboushleib Hamida M.
Published: March 2009

A series of 3‐(N‐substituted thiocarbamoyl)hydrazino‐1,2,4‐triazino[5,6‐b]indole derivatives 3–22 has been synthesized and evaluated for in vitro antimicrobial activity. Although some of the products displayed significant activity against Staphylococcus aureus, Escherichia coli and Candida albicans, their bactericidal and bacterostatic potencies were lower than that of penicillin G. The structure of the products was assigned upon the basis of their infrared, 1H‐nmr and 13C‐nmr spectra.
Synthesis of pyrido[1′,2′:1,2]imidazo[4,5‐b]pyrazines from 2‐amino‐3‐chloro‐5,6‐dicyanopyrazine with substituted pyridines
Authors: Mitsuhashi Keiryo , Nagae Yasushi , Suzuki Toshinobu
Published: March 2009

Novel synthesis of the title compounds by the cyclization between 2‐amino‐3‐chloro‐5,6‐dicyanopyrazine and various substituted pyridines is described.
Convenient synthesis of substituted 3‐aminothiophene‐2‐carbonitriles from α‐acetylenic nitriles and their conversion to thieno[3,2‐d]pyrimidines
Authors: Ren Wu‐Yun , Rao Kambhampati V. B. , Klein Robert S.
Published: March 2009

Several novel 2,4,6‐trisubstituted thieno[3,2‐d]pyrimidines were synthesized from the hitherto unknown 3‐amino‐5‐methyl‐(or 5‐phenyl)thiophene‐2‐carbonitriles 7 and 8. o‐Aminonitriles 7 and 8 were obtained in a single step by conjugate addition of mercaptoacetonitrile (generated in situ) to substituted acetylenic nitriles 4 and 5 and annelation of the intermediate vinylic thioethers.
One‐Pot synthesis of unsymmetrically substituted 2,4‐dialkylisoflavenes
Authors: Alberola Angel , Andrés Celia , Ortega Alfonso González , Pedrosa Rafael , Vicente Martina
Published: March 2009

The trimethylsilyl derivative of formonometine reacts sequentially with two different organometallic derivatives to afford regiospecifically and with good yield 2,4‐dialkylisoflavenes unsymmetrically substituted.
Heterocycles. IX. Synthesis of new substituted benzo[h]quinolones
Authors: El‐Rayyes N. R. , Al‐Saleh B. , Al‐Omran F. , Edun M.
Published: March 2009

2‐Arylidine‐1‐tetralones I were condensed with phenyl‐, p‐chlorophenyl‐, and p‐methoxyphenylacetamides A in the presence of a base to yield the corresponding benzo[h]quinolones II‐IV. Dehydrogenation of compounds II gave the benzoquinolones V which upon acetylation yielded the corresponding 2‐acetyl derivatives VI. The structure of all products was substantiated by chemical and spectral methods.
Non conventional syntheses of heterocyclic compounds. 2. Synthesis of 1H‐4,5‐dihydro‐1,3,4‐benzotriazepine derivatives
Authors: Fusco Raffaello , Marchesini Alessandro , Sannicolò Franco
Published: March 2009

Arylazoanils carrying aromatic methyl or ethyl groups in the position ortho to the imine function thermally cyclize to give 1H‐4,5‐dihydro‐1,3,4‐benzotriazepine derivatives in fairly good yields. A study of the effect of the substituents on both the aryl rings is reported. The reaction is interpreted as an internal oxo‐reduction process.
Synthesis of 5,6‐dimethoxyquinazolin‐2(1H)‐ones
Authors: Press Jeffery B. , Bandurco Victor T. , Wong Elizabeth M. , Hajos Zoltan G. , Kanojia Ramesh M. , Mallory Robert A. , Deegan Edward G. , Mcnally James J. , Roberts Jerry R. , Cotter Mary Lou , Graden David W. , Lloyd John R.
Published: March 2009

Synthesis of 5,6‐dimethoxyquinazolin‐2(1H)‐one derivatives was the subject of investigations leading to the preparation of title compounds 11, 13, 14 and 26. Target quinazolines 1 were synthesized in three ways; the route starting from o‐vanillin via the intermediacy of 6‐amino‐2,3‐dimethoxyacetophenone (19) was used for most of the preparative work. The unexpected formation of an acid‐labile dimer of 13 was discovered and solid state 13C nmr was used for structural assignment. The 5‐methoxy substituent in these systems shows anomalous spectral characteristics and, in one case, was cleaved in acid media to 22.
Conversion of 4‐amino‐1H‐1,5‐benzodiazepine‐3‐carbonitrile to pyrazolo[3,4‐d]pyrimidines, pyrimido[1,6‐a]benzimidazole, and pyrazolo[3′,4′:4,5]pyrimido[1,6‐a]benzimidazoles
Authors: Okamoto Yoshihisa , Togo Isao , Kurasawa Yoshihisa , Takagi Kaname
Published: March 2009

The reactions of multifunctional compounds 2a, b, c, 3a, b and 4a, b which were readily obtained from 4‐amino‐1H‐1,5‐benzodiazepine‐3‐carbonitrile 1 with orthoesters are described, and derivatives of pyrazolo‐[3,4‐d]pyrimidines 5, pyrimido[1,6‐a]benzimidazole 9, and pyrazolo[3′,4′:4,5]pyrimido[1,6‐a]benzimidazole 10 are synthesized.
A facile synthesis of 5,7‐dihydro‐5‐oxopyrido[3′,2′:5,6]pyrimido[1,2‐a]benzimidazoles. A new heterocyclic ring system
Authors: Caroti Paola , Ceccotti Carlo , Da Settimo Antonio , Palla Fabio , Primofiore Giampaolo
Published: March 2009

Reaction between 2‐chloropyridine‐3‐carbonyl chloride and 1‐alkyl‐2‐aminobenzimidazoles afforded the N‐(1‐alkylbenzimidazole‐2‐yl)‐2‐chloropyridine‐3‐carboxamides, which were cyclized to 5,7‐dihydro‐5‐oxopyrido[3′,2′:5,6]pyrimido[1,2‐a]benzimidazoles. The assigned structures of these hitherto unknown heterocyclic compounds were confirmed by their ir and 1H nmr spectra and chemical evidence.
Synthesis and reactions of 3‐iodo‐4H‐pyran‐4‐ones
Authors: Marei Mohamed Gaber , Mishrikey Morcos Michael , El‐Kholy Ibrahim El‐Sayed
Published: March 2009

3‐Iodo‐4H‐pyran‐4‐ones have been synthesised in excellent yield by the reaction of acetylenic β‐diketones with iodine monochloride and were converted into the corresponding 4H‐pyran‐4‐thiones. The iodopyrones and thiopyrones gave with methylamine the respective N‐methylpyridones and thiopyridones. The structure of the above compounds was confirmed from their spectral characteristics.
Heterocyclen aus α‐nitroolefinen. XII . 3‐Acetyl‐4,5‐dihydro‐5‐(methylenamino)furane und 3‐acylpyrrole aus α‐nitroolefinen und β‐diketonen
Authors: Boberg Friedrich , Garburg Karl‐Heinz , Görlich Karl‐Joachim , Pipereit Eberhard , Redelfs Elke , Ruhr Maria
Published: March 2009

From α‐nitroolefines 1 and β‐diketones 2 3‐acetyl4,5‐dihydro‐5‐(methy1eneamino)furans 5 are prepared. Furans 5 react in acid medium to yield 1‐unsubstituted 3‐acylpyrroles 6, catalytic hydrogenation yields 1‐substituted 3‐acylpyrroles 9. The 1H‐nmr and 13C‐nmr investigations prove the constitutions.
Syntheses and configurations of some heterocyclic amidoximes. X‐Ray crystal structure of 3‐phenyl‐5,6‐dihydro‐2(1H)‐pyrazinone‐O‐methyloxime
Authors: Johnson James Elver , Maia Joanne A. , Tan Karen , Ghafouripour Abdolkarim , De Meester Patrice , Chu Shirley S. C.
Published: March 2009

O‐Methyl‐α‐ketophenylacetohydroximoyl chloride (1) was prepared by the reaction of O‐methyl‐α‐methoxyphenylacetohydroximoyl chloride (5) with N‐bromosuccinimide and concentrated hydrobromic acid. Reaction of 1 with ethylenediamine gave 3‐phenyl‐5,6‐dihydro‐2(1H)‐pyrazinone‐O‐methyloxime (6). 3‐Phenyl‐5,6‐cyclohexano‐5,6‐dihydro‐2(1H)‐pyrazininone‐O‐methyloxime (7) was prepared by reaction of 1 with trans‐1,2‐diaminocyclohexane. The X‐ray structure of 6 has been determined. The crystals are orthorhombic, space group Pbca with a = 10.264(3), b = 18.262(4), c = 23.530(4)Å, V = 4411(2)Å3, and Z = 16. The structure, which was refined to R = 0.038 using 1652 observed reflections, shows the amidoxime moiety to be the Z configuration. Reaction of benzohydroximoyl chloride with aziridine gave (Z)‐aziridinylbenzaldoxime (16a). Ultraviolet irradiation of a benzene solution of 16a gave a mixture of the Z and E isomers 16a and 16b. The E isomer 16b underwent thermal isomerization to 16a at 100°. Reaction of 16a with dimethyl sulfate in sodium hydroxide solution gave (Z)‐O‐methylaziridinylbenzaldoxime (17a). Photoisomerization of a hexane solution of 17a gave a mixture of the Z and E isomers 17a and 17b which were separated by preparative glc. The isomers 17a and 17b are resistant to thermal Z = E isomerization. The mechanisms of thermal isomerization of benzamidoximes are discussed.
2‐Metylthiazolium salts as 1,4‐dinucleophiles. Thiazolo[3,2‐a]pyridinium salts from westphal condensation
Authors: Galera C. , Vaquero J. J. , Navio J. L. Garcia , Alvarez‐Builla J.
Published: March 2009

Condensation of 2‐methylthiazoliura salts with 1,2‐dicarbonyls in the presence of base, yielded thiazolo‐[3,2‐a]pyridinium derivatives. Results with different substrates are discussed.
Reaction of pyrazine‐2,3‐dicarbonitrile and 1,3‐dimethyllumazine with alkyl radicals
Authors: Tada Masaru , Ito Takayori , Ohshima Kaoru
Published: March 2009

Pyrazine‐2,3‐dicarbonitrile (1) reacts with alkyl radicals to give mono‐ 3 and di‐alkylated pyrazine‐2,3‐dicarbonitriles 4. Similarly 1,3‐dimethyllumazine (2) reacts with alkyl radicals to give 7‐alkyl‐1,3‐dimethyllumazines 8 as the major product. The reactivity of alkyl radicals decreases in the order tertiary, secondary, and primary, and 1 is more reactive than 2 in those radical substitution reactions.
Beckmann rearrangement of (+)‐3‐methoxy‐17‐methylmorphinan‐10‐one oxime
Authors: Mohacsi Erno
Published: March 2009

(+)6,7,7a,8,9,10,11,11a‐Octahydro‐2‐methoxy‐12‐methyl‐5H‐7,11a‐irninoethanodibenz[c, e]azepin‐5‐one (3) was prepared by Beckmann rearrangement of the oxime of (+)‐3‐methoxy‐17‐methylmorphinan‐10‐one (2) with polyphosphoric acid.
Syntheses of 1,3,8,10,12‐pentazanaphthacene‐2,4,7,9‐(12H,3H,8H,10H)‐tetraones (linear pyrimidine‐fused 5‐deazaflavins), 1,3,6,8,12‐pentazabenz[a]anthracene‐2,4,7,9(12H,3H,6H,8H)‐tetraones(bent pyrimidine‐fused 5‐deazaflavins), and their flavin analogs
Authors: Yoneda Fumio , Koga Masakazu
Published: March 2009

1,3,8,10,12‐Pentazanaphthacene‐2,4,7,9(12H,3H,8H,10H)‐tetraones (linear pyrimidine‐fused 5‐deazaflavins) and 1,3,6,8,12‐pentazabenz[a]anthracene‐2,4,7,9(12H,3H,6H,8H)‐tetraones (bent pyrimidine‐fused 5‐deazaflavins) were synthesized by condensation of 7‐alkylaminoquinazoline with 6‐chloro‐5‐formyl‐3‐methyluracil. Also, their flavin analogs, 1,3,5,8,10,12‐hexazanaphthacene‐2,4,7,9(12H,3H,8H,10H)‐tetraones (linear pyrimidine‐fused flavins) and l,3,5,6,8,12‐hexazabenz[a]anthracene‐2,4,7,9(12H,3H,6H,8H)‐tetraones (bent pyrimidine‐fused flavins) were synthesized by cyclization of 7‐[N‐alkyl‐N‐(5‐nitrouracil‐6‐yl)]aminoquin‐azolines with the Vilsmeier reagent.
A simple synthesis of a new family of polycyclic oxygen containing heterocycles
Authors: Geoffrey Philippe , Carre Marie‐Christiane , Caubere Paul , Ianelli Sandra , Nardelli Mario
Published: March 2009

Benzocyclobutenols 1 were transposed by boron trifluoride etherate in the presence of triethylsilane into a new family of heterocycles 2.
Spirocyclization of 1‐(o‐aminophenyl)cycloalkanols and 1‐(2′‐amino‐3′‐pyridinyl)cycloalkanols
Authors: Canonne Persephone , Boulanger Raynald , Chantegrel Bernard
Published: March 2009

A one‐step synthesis of spiro[cycloalkane‐1,4′‐2H‐3′,1‐benzoxazin]‐2′‐ones and spiro[cycloalkane‐1,4′‐1H‐pyrido[2′,3′‐d][1,3′]oxazin]‐2′‐ones, obtained in good yield from the corresponding 1‐(o‐aminophenyl) and 1‐(2′‐amino‐3′‐pyridinyl)cycloalkanols is described using ethyl carbonate in presence of n‐butyllithium.
Novel chromophoric heterocycles based on maleimide and naphthoquinone
Authors: Katritzky Alan R. , Fan Wei‐Qiang , Li Qiao‐Ling , Bayyuk Shibli
Published: March 2009

1‐Phenyl‐3,4‐dichloromaleimide, 1‐n‐propyl‐3‐bromomaleimide, and 2,3‐dichloro‐1,4‐naphthoquinone have been condensed with various mono‐ and bis‐nucleophiles to yield a range of novel dyes and pigments. Their visible absorption spectra are discussed.
Synthesis of 2,2,4‐trisubstituted‐1,2‐dihydroquinazolines
Authors: Strekowski Lucjan , Cegla Marek T. , Kong Suk‐Bin , Harden Donald B.
Published: March 2009

Synthesis of 2,2,4‐trisubstituted‐1,2‐dihydroquinazolines 6 from readily available 2‐aminobenzonitrile (1) is described. The scope and limitations of the method are discussed.
Pyridazines. XLI synthesis of novel pyrido[3,4‐d]pyridazine derivatives from 4,5‐disubstituted pyridazines
Authors: Boamah Philip Yaw , Haider Norbert , Heinisch Gottfried
Published: March 2009

Pyrido[3,4‐d]pyridazines 2–5, 21 bearing one, two, or three aryl substituents in the pyridine moiety are shown to be conveniently accessible from 4‐aroyl‐5‐methylpyridazines or 4,5‐diaroylpyridazines, respectively, by condensation reactions with appropriate C‐N fragments. In addition, the novel pyridazine‐annelated pyridones 24, 25 were found to be easily available from ethyl 5‐methyl‐4‐pyridazinecarboxylate.
Mitt. XV: Struktur und reaktivität von isoanellierten heterocyclischen systemen mit 4nπ‐ und (4n + 2) π‐elektronen. 2‐t‐butyl‐4‐methyl‐2,4‐dihydropyrrolo[3,4‐b]indole. reaktionen mit aktivierten CC‐dienophilen
Authors: Dyker Gerald , Kreher Richard P.
Published: March 2009

Reactions of 2‐t‐butyl‐4‐methyl‐2,4‐dihydropyrrolo[3,4‐b]indoles with N‐aryl‐maleimides have been investigated. The formation of 1:1‐cycloadducts is influenced by substituents at 1,3‐position. The consecutive transformations of these intermediates can be controlled by nucleophilic solvents or reagents. Ring opening reactions occur at the labile N,O‐acetal group of the cycloadducts followed by eliminaton or addition reactions.
The chemistry of 2H‐3,1‐benzoxazine‐2,4(1H)‐dione (isatoic anhydride). 21. a mild process for the preparation of 10‐alkyl‐9‐acridanones and it's application to the synthesis of acridone alkaloids
Authors: Coppola Gary M. , Schuster Herbert F.
Published: March 2009

10‐Substituted‐9‐acridanones are readily prepared by the reaction of the corresponding isatoic anhydride with the lithium enolate of 2‐cyclohexen‐1‐one. The initially formed product, the 1,2‐dihydroacridone need not be purified but can be aromatized directly with DDQ to the desired acridone. This methodology is applicable to the synthesis of acridone natural products. Two alkaloids, 1,2,3‐trimethoxy‐10‐methylacridone (9) and evoxanthine (10), were prepared from 4,5,6‐trimethoxy‐N‐methylisatoic anhydride and 6‐methoxy‐4,5‐methyl‐enedioxy‐N‐methylisatoic anhydride respectively. In these trioxygenated systems, palladium‐on‐charcoal must be used to aromatize the penultimate intermediate.
Synthesis, structural and conformational study of some esters derived from 8‐phenethyl‐8‐azabicyclo[4.3.1]decan‐10α‐ol
Authors: Gálvez E. , Arias M. S. , Rico B. , Ardid I. , Florencio F. , Sanz J.
Published: March 2009

A series of 10α‐acyloxy‐N‐phenethyl‐8‐azabicyclo[4.3.1]decane derivatives have been synthesized and studied by 1H and 13C nmr spectroscopy, and the crystal structure of N‐phenethyl‐10aL‐(xanten‐9″‐carbonyloxy)bicyclo[4.3.1]decane 2 has been determined by X‐ray diffraction. The compounds studied display in deuteriochloroform the same preferred conformation adopted by the piperidine ring as a distorted chair conformation flattened at N‐8 with both the phenethyl and acyloxy groups in the equatorial position with respect to the piperidine ring. These results are in close agreement with that found for compound 2 in the crystalline state.
1,3‐Dipolar cycloaddition reactions. Regioselective synthesis of heterocycles and theoretical studies
Authors: Pierini Adriana B. , Cardozo Mario G. , Montiel Aida A. , Albonico Sem M. , Pizzorno Maria T.
Published: March 2009

We report a 1,3‐dipolar cycloaddition reaction between a oxazolium 5‐oxide derivative with chloroacrylonitrile or ethyl propiolate as dipolarophiles, in order to obtain substituted pyrrolizidines. Experimentally we found that the reaction is regiospecific with chloroacrylonitrile and regioselective with ethyl propiolate. The secondary attractive orbital interactions from the Frontier Molecular Orbital Theory, the differences in stability of the possible biradical intermediaries postulated for the reaction and some hindrance effects, explain the regioselectivity observed experimentally.
Synthèse de dimethyl‐2,2 chromannediones‐3,4: Condensation avec les ortho‐diaminopyridines
Authors: Vinot Nicole , Maitte Pierre
Published: March 2009

Les diméthyl‐2,2 chromannediones ont été préparées par oxydation des chromanones correspondantes à l'aide du nitrite d'isoamyle. Dans la majorité des cas, les monocétones sont elles‐měmes obtenues par action de l'acide méthyl‐3 butène‐2 oïque sur un phénol substitué, en présence d'acide polyphosphorique. La condensation des chromannediones avec les orthodiaminopyridines permet d'obtenir des benzopyrannopyridopyrazines qui, du fait de la dissymétrie des réactifs, sont le plus souvent un mélange d'isomères.
Pyrrolo[1,4]benzodiazepines. IV. Synthesis of E‐ and Z‐5,11‐dioxo‐11a‐ethoxycarbonyl‐2‐ethylidene‐1,2,3,10,11,11a‐hexahydro‐5H‐pyrrolo[2,1‐c][1,4]benzodiazepine
Authors: De Caprariis P. , De Martino G. , Abignente E. , Avara P. , Mayol L.
Published: March 2009

Preparation of the title compound starting from 4‐acetyl‐2,2‐diethoxycarbonyl‐2,3‐dihydro‐1‐(2‐nitro‐benzoyl)‐1H‐pyrrole by selective reduction is described; its E and Z forms were isolated and their geometrical structure assigned on the basis of 1H and 13C nmr spectral data.
Synthesis of potential antifilarial agents 2 . methyl 2‐substituted purine 8‐carbamates and related compounds
Authors: Ram Siya , Evans William , Wise Dean S. , Townsend Leroy B. , Mccall John W.
Published: March 2009

A series of methyl 2‐substituted purine 8‐carbamates was prepared and evaluated for antifilarial activity. These purines were synthesized as aza congeners of benzimidazole carbamates which have shown significant anthelmintic activity to determine the effect that this modification might have on anthelmintic activity. The compounds were tested against the filarial infection, B. pahangi, in jirds. None of the compounds prepared in this study demonstrated antifilarial activity.
Novel diphenysulphapyrimidine acetates derived from chalcones
Authors: Usifoh C. O. , Olugbade T. A. , Onawumi G. O. , Oluwadiya J. O. , Reisch J.
Published: March 2009

Cyclocondensation of sulphaguanidine acetate with chalcones in dimethylsulphoxide at 110° gave 4,6‐diphenylsulphapyrimidine acetates.
Synthesis of 3,4,5‐triamino‐4H‐1,2,4‐triazole (guanazine) and its 4‐arylideneamino derivatives
Authors: Emilsson Håkan
Published: March 2009

Synthetic methods for the preparation of 3,4,5‐triamino‐4H‐1,2,4‐triazole (guanazine) and its 4‐arylidene‐amino derivatives are described. Guanazine, which can be used as an appropriate starting material in the syntheses of different bicyclic heterocycles, was readily obtained from thiosemicarbazide by treatment with mercuric oxide. Guanazine was also obtained from the S‐methylisothio ether of thiosemicarbazide via a pyrolytic reaction. The 4‐arylideneamino derivatives were either prepared by treatment of guanazine with an appropriate aromatic aldehyde, or by methods in which 1‐arylidene‐5‐thiocarbamoyldiaminoguanidines are used as starting materials.
Studies in spiroheterocycles. Part XVII. synthesis of novel fluorine containing spiro[indole‐pyranobenzopyran] and spiro[indenopyran‐indole] derivatives
Authors: Joshi Karishna C. , Dandia Anshu , Baweja Sunita , Joshi Amitabh
Published: March 2009

An elegant one‐step synthesis of two novel spiro ring systems viz: spiro[3H‐indole‐3,4′‐(2′‐amino‐3′‐carbonitrile‐[4′H]‐pyrano[3,2‐c]benzopyran)]‐2,5′(1H)‐dione8 and spiro[(2‐amino‐3‐carbonitrile‐indeno[1,2‐b]pyran)‐4(5H)>3′‐[3H]indole]‐2′,5(1′H)‐diones in 80–85% yields is described. The spiro heterocycles were prepared by the reactions of fluorine containing 3‐dicyanomethylene‐2H‐indol‐2‐ones with 4‐hydroxy‐2H‐1‐benzopyran‐2‐one and 1H‐indene‐1,3(2H)‐dione respectively. The synthesized compounds have been characterized on the basis of elemental analyses, ir, pmr, 19F nmr and mass spectral data.
The x‐ray crystal and molecular structure of chloro‐α,β,γ,δ‐tetraphenylporphinatopyridinegallium(III)
Authors: Radish K. M. , Cornillon J.‐L. , Korp J. D. , Guilard R.
Published: March 2009

Crystals of the title compound C49H33N5ClGa·1/2C5H5N·1/2C5H12 [Ga(py)(Cl)(TPP)]·1/2(py)·1/2(n‐pen) are monoclinic, P21/n, a = 13.162(2), b = 23.422(6), c, = 14.677(2) Å, β = 101.47(1)°, and Z = 4. The crystal structure refined to R = 0.056 for 2249 observed reflections. The coordination polyhedron of the gallium atom is an octahedron, and the distances between the central metal and axial ligands are Ga‐Cl = 2.328(1) and Ga‐py = 2.274(3) Å. The gallium atom is displaced slightly out of the porphyrin plane towards Cl, 0.14 Å from the 4N plane and 0.16 Å from the mean porphinato plane, with an average Ga‐N distance of 2.01 Å. Although the complex is isostructural with the Mn and Co analogs, it is the first reported structure of a monomeric hexacoordinate gallium(III) porphyrin.
Synthesis of 5‐benzoyl‐5‐phenyl‐ and 5‐phenylhydroxymethyl‐5‐phenylhydantoins as potential anticonvulsants
Authors: Crooks Peter A. , Deeks Trevor , Desimone Francesco
Published: March 2009

A series of 5‐benzoyl‐5‐phenyl‐ and S‐phenyl‐5‐phenylhydroxymethylhydantoins have been synthesized from the reaction of urea, N‐monosubstituted ureas and sym‐N‐N‐disubstituted ureas with phenyltriketone hydrate, via a pinacol‐pinacolone‐type rearrangement mechanism. The compounds were evaluated for anti‐convulsant activity in mice.
Synthesis and spectral properties of new 6‐methoxy‐3‐(2′‐thienyl)‐1,2‐benzisoxazole and its isomeric benzoxazole
Authors: Varache‐Béranger Marline , Nuhrich Alain , Devaux Guy , Duboudin Françoise
Published: March 2009

6‐Methoxy‐3‐(2′‐thienyl)‐1,2‐benzisoxazole has been prepared simultaneously with 6‐methoxy‐2‐(2′‐thienyl)‐1,3‐benzoxazole. The spectral data of these new compounds have been discussed. Mass spectroscopy has proved to be a valid tool in the structural characterization of these isomers and 13C nmr spectrometry confirmed their structures.
Alkyl substituted 3‐PPP derivatives. Synthesis and biological investigation
Authors: Tecle Haile , Bergmeier Stephen C. , Wise Lawrence D. , Hershenson Fred M. , Coughenour Linda L. , Heffner Thomas G.
Published: March 2009

Synthesis of alkyl substituted derivatives of 3‐(1‐propyl)3‐piperidinyl)phenol (3‐PPP), 2–8, was carried out in an attempt to improve on the pharmacodynamic properties of 3‐PPP. No significant improvement was attained.
Etude des conditions d'accés aux 6H‐, 7H‐ et 11H‐pyrimidino‐[4,5‐a], [4,5‐b], [5,4‐a] [5,4‐b] et [5,4‐c]carbazoles. 1
Authors: Gazengel Jean‐Marie , Lancelot Jean‐Charles , Rault Sylvain , Robba Max
Published: March 2009

Les dihydropyrimidinocarbazoles 12,15 et 18 sont accessibles par cyclisation des tétrahydrocarbazolones 11, 14 et 17 au moyen du triformamidométhane dans le formamide. Leur oxydation par le permanganate conduit aux pyrimidinocarbazoles 13, 16 et 19. Les aminocyanocarbazoles 1 et 7 constituent des intermédiaires permettant l'accés aux oxo 6H‐pyrimidinocarbazoles 2 et 8. La quinazolinylhydrazone 9, par chauffage en milieu acide permet, après cyclisation, d'accéder au tétrahydro 6H‐pyrimidinocarbazole 10. Les spectres de rmn confirment la structure des dérivés obtenus.
Synthesis and antibacterial activity of some 7‐substituted 1‐ethyl‐6‐fluoro‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acids: Ethers, secondary amines and sulfides as c‐7 substituents
Authors: Ziegler Carl B. , Curran William V. , Kuck Nydia A. , Harris Sonja M. , Lin Yang‐I.
Published: March 2009

A series of 7‐substituted 1‐ethyl‐6‐fluoro‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acids were prepared from 1‐ethyl‐6,7‐difluoro‐1,4‐dihydro‐4‐oxoquinoline‐3‐carboxylic acid 8. Those derivatives reported contain acyclic and heterocyclic substituents linked to the quinolone C‐7 position via O, NH or S. The in vitro antibacterial data of some of these derivatives against 4 Gram positive and 4 Gram negative organisms are reported.
New 7‐substituted quinolone antibacterial agents. II. The synthesis of 1‐ethyl‐1,4‐dihydro‐4‐oxo‐7‐(pyrazolyl, isoxazolyl, and pyrimidinyl)‐1,8‐naphthyridine and quinolone‐3‐carboxylic acids
Authors: Domagala John M. , Peterson Phred
Published: March 2009

Synthetic methods for the construction of certain aromatic heterocyclic side chains for the quinolone anti‐bacterials have been provided. In particular a series of 7‐(pyrazol‐3 or 4‐yl, 4‐ or 5‐isoxazolyl and 4‐ or 5‐pyrimidinyl)‐1‐ethyl‐1,4‐dihydro‐4‐oxo‐1,8‐naphthyridine and quinoline‐3‐carboxylic acids have been prepared. All of the heterocycles were prepared from masked 1,3‐dicarbonyl derivatives of nalidixic acid (9,17) or 7‐acetyl‐1‐ethyl‐1,4‐dihydro‐4‐oxo‐3‐quinoline carboxylic acids (8). These masked 1,3‐dicarbonyl derivatives were prepared by the use of t‐butoxy‐bis‐dimethylaminomethane on the activated methyls of 9,19 and 8. The pyrimidinyl analogs, substituted with a 2‐amino or a 2‐aminomethyl moiety, were the only derivatives with substantial antibacterial activity.
Photochemical conversion of o‐phenylenediamine and o‐aminophenol into heterocyclics
Authors: Crank G. , Makin M. I. H.
Published: March 2009

o‐Phenylenediamine is photo‐oxidized to phenazine‐2,3‐diamine in ethanolic or aqueous hydrochloric acid solution. In acetic or propionic acid solutions it forms benzimidazole derivatives. o‐Aminophenol in ethanol is photo‐oxidized to 2‐amino‐3H‐phenoxazin‐3‐one and two tetracyclic solvent addition products.
Synthesis and tautomerism of ethyl 2‐(2‐benzothiazolyl)‐2‐(6‐purinyl)acetate and related compounds
Authors: Klemm L. H. , Johnstone Susan , Tran Long K.
Published: March 2009

Reaction of 6‐chloro‐9H‐(2‐tetrahydropyranyl)purine (2d) with the sodium salt of ethyl benzothiazole‐2‐ace‐tate (1) in dimethylformamide effects condensation of the two compounds (with loss of sodium chloride) to give the corresponding ethyl diarylacetate 4 (35%), present largely as an enol chelate tautomer. Isolated as a by‐product is 6‐(2‐aminophenyl‐1‐thio)‐9H‐(2‐tetrahydropyranyl)‐purine (4%), formed via opening of the thiazole ring. Removal of the tetrahydropyranyl protective group from 4 occurs by treatment with p‐toluenesulfonic acid in aqueous ethanol to produce ethyl benzothiazole‐2‐(6‐purinyl)acetate (80%), existent largely as two enol chelate isomers. Spectral data for the various products are presented. An attempt to use 6‐chloro‐9‐acetyl‐9H‐purine in place of 2d in the first reaction gives acetylation of 1 instead of condensation.
The preparation of 3,4‐dihydro‐1‐benzoxepin‐5(2H)‐ones
Authors: Freedman Jules , Stewart Kenneth T.
Published: March 2009

Several methods for the preparation of 3,4‐dihydro‐1‐benzoxepin‐5(2H)‐ones are described. In addition to the desired ketones, a variety of novel by‐products have been isolated.
First reactions of dialkoxycarbenium tetrafluoroborates with pyrroles, 5H‐dibenz[b,f]azepines, and electron‐rich arenes
Authors: Pindur U. , Flo C.
Published: March 2009

Pyrrole (2a) and 2,5‐dimethylpyrrole (2b) react with the dialkoxycarbenium tetrafluoroborates 1a‐1c under kinetic control to yield the corresponding acylpyrrole derivatives. 5H‐Dibenz[b,f]azepine (9a) and the 10,11‐dihydro derivative 9b react only with the most electrophilic of the series of electrophiles tested, namely, diethoxycarbenium tetrafluoroborate (1a), to furnish the corresponding formyl derivatives. Similarly, in arene chemistry, the highly electron‐rich N,N‐dimethylaniline (13a) and 1,3,5‐trimethoxybenzene (13b) are formylated by reaction with 1a.
Synthesis and study of chiral NADH models in the thieno[2,3‐b]pyridine series
Authors: Bench R. , Duflos J. , Dupas G. , Bourguignon J. , Queguiner G.
Published: March 2009

Thieno[2,3‐b]pyridine derivatives, functionalized on the thiophene ring have been synthesized in two different ways: electrophilic substitution of thieno[2,3‐b]pyridine derivatives or construction of a pyridine ring starting from disubstituted thiophene compounds. The products obtained were used in the synthesis of chiral NADH models.
Approaches to the synthesis of benzo[c]phenanthridines
Authors: Blaskó Gábor , Cordell Geoffrey A.
Published: March 2009

6‐Methylbenzo[c]phenanthridine derivatives were synthesized via an established route and their cytotoxic activity determined. Attempts to synthesize benzo[c]phenanthridines lacking the 6‐methyl group via a 2‐ben‐zopyrylium intermediate were unsuccessful.
Tricyclic heteroaromatic systems. 5H‐1,2,3‐triazolo[5,1‐c][1,4]benzodiazepine
Authors: Melani F. , Cecchi L. , Colotta V. , Filacchioni G.
Published: March 2009

The synthesis of the new tricyclic system 5H‐1,2,3‐triazolo[5,1‐c][1,4]benzodiazepine, diaza‐analogue of 5H‐pyrrolo[2,1‐c][1,4]benzodiazepine, which is the common feature of some antitumor antibiotics, is reported. The structure of the new tricyclic system and of some of its key intermediates is assigned by means of a 13C nmr study.
Nitroimidazoles. V. Synthesis of 1‐methyl‐2‐(2‐methyl‐4‐thiazolyl)nitroimidazoles
Authors: Shafiee A. , Shahocini S.
Published: March 2009

Reaction of readily available 2‐methyl‐4‐formylthiazole (1) with glyoxal and ammonia gave 2‐(2‐methyl‐4‐thiazolyl)imidazole (2). Nitration of 2 with a mixture of nitric acid‐sulfuric acid at 100° yielded 2‐(2‐methyl‐4‐thiazolyl)‐4,5‐dinitroimidazole (3) as the sole reaction product, while nitration at 65° afforded 2‐(2‐methyl‐4‐thiazolyl)‐4‐(or 5)‐nitroimidazole (4). N‐Methylation of compound 4 in the presence of base gave 1‐methyl‐2‐(2‐methyl‐4‐thiazolyl)4‐nitroimidazole (6), whereas N‐methylation with diazomethane afforded 1‐methyl‐2‐(2‐methyl‐4‐thiazolyl)‐5‐nitroimidazole (5). N‐Methylation of compound 3 yielded 1‐methyl‐2‐(2‐methyl‐4‐thiazolyl)‐3,5‐dinitroimidazole (7) in high yield.
Examination of the dipolarophilicity of ethylene and nitrile functions in the cycloaddition of mesitonitrile oxide to isopropylidenemalononitrile
Authors: Lianis P. S. , Rodios N. A. , Alexandrou N. E.
Published: March 2009

Mesitonitrile oxide reacts with isopropylidenemalononitrile to give mono‐ and bis‐1,2,4‐oxadiazole derivatives 2 and 3 and Δ2‐soxazolines 4 and 5 in moderate yields. The dipolarophilic character of the ethylene and nitrile functions in these cycloadditions is examined.
Synthese de dihydro‐6,7 benzo‐b [1H] azonines par extension de cycle de dihydro‐4,5 benzo‐b [1H] azepines
Authors: Nisole Christian , Uriac Philippe , Huet Jean
Published: March 2009

L'addition, suivie d'électrocyclisation, d'acétyléniques activés sur des dihydro‐4,5 benzo‐b [1H] azépines, ènamines hétérocycliques, permet la synthèse de dihydro‐6,7 benzo‐b [1H] azonines dont la structure est établie par spectrométrie de masse, rmn 1H et rmn 13C.

Activated acetylenic reagents add to heterocyclic enamines 4,5‐deihydor‐1H‐beenzo[b]azepines and by electrocyclisation, give 6,7‐deihydor1Hbeenzo[b]azepines. The structure of those new heterocycles is demonstrated by mass, 1H and 13C nmr.
3‐Aryl‐5‐[(aryloxy)methyl]‐3‐[(1H‐1,2,4‐triazol‐1‐yl)methyl]‐2‐methylisoxazolidine derivatives. Synthesis and antifungal activity
Authors: Bennett Grace A. , Swift Patricia A. , Mullen George B. , Allen Stanley D. , Mitchell Jeffrey T. , Jones Wendy E. , Georgiev Vassil St.
Published: March 2009

The synthesis and antifungal activity of a novel series of 3‐aryl‐5‐[(aryloxy)methyl]‐3‐[(1H‐1,2,4‐triazol‐1‐yl)‐methyl]‐2‐methylisoxazolidines are described. The in vitro activity was evaluated in solid agar cultures against a variety of dermatophytes and yeast fungi, while in vivo activity was measured in an immune‐compromised mouse model of systemic candidiasis. The activity of the title series was compared to that of ketoconazole and one derivative, the cis‐3‐(4‐chlorophenyl)‐5‐(4‐chlorophenyloxy)methyl analogue 5f was found to possess a similar potency in the in vivo assay. Structure‐activity relationship correlations are also discussed.
Preparation of azolopyridazinecarboxylic acids
Authors: Heinisch G. , Lötsch G. , Offenberger S. , Stanovnik B. , Tisler M.
Published: March 2009

Oxidation reactions of various methyl substituted azolopyridazines 2a‐d, 3a‐h, 4a,b were investigated in order to gain access to the title compounds. This procedure was found to be of limited scope affording only the carboxylic acids 5, 7 and 9. A variety of novel azolopyridazinecarboxylic acid methyl esters bearing one or two methoxycarbonyl groups at the pyridazine core 17,18 and 12,14,16, 20, respectively, however, could be prepared by means of a regioselective radical substitution process.
Synthesis and configuration of 4‐alkyl‐2‐methyl‐3,4‐diphenyl‐1,2‐thiazetidine 1,1‐dioxide
Authors: Grander Evelyne , Leclerc Gérard , Ehrhardt Jean‐Daniel
Published: March 2009

4‐Alkyl‐2‐methyl‐3,4‐diphenyl‐1,2‐thiazetidine 1,1‐dioxide 5, 6 and 7 were obtained from 2‐methyl‐3,4‐diphenyl‐1,2‐thiazetidine 1,1‐dioxide 1 by reaction of its anion 4 with alkyl halides. cis‐ and trans‐Configuration of the 4‐alkylated products were determined by 1H‐nmr and NOE difference spectro‐scopy studies.
Synthesis and derivatization of novel 4‐aroylthiophene‐and furan‐2‐sulfonamides
Authors: Hartman George D. , Halczenko Wasyl
Published: March 2009

Sulfonation of 3‐aroylthiophenes and furans with sulfuric acid in acetic anhydride regioselectively affords the corresponding 2,4‐disubstituted heterocycle. Benzylamine derivatives of the parent sulfonamides are obtained either by Mannich reaction of aryl phenols, orviaa sequence employing free radical bromination followed by selective ammonolysis. This methodology provides ready access to a wide variety of regioselectively‐substituted heterocycles.
Studies in spiroheterocycles. Part XIII. Synthesis of a novel spiro system: Spiro[9H‐acridine‐9,3′‐[3h]indol]‐2′(1′H)‐one and related compounds from new fluorinated spiro[3H‐indole‐3,9′‐[9H]xanthen]‐2(1H)‐ones
Authors: Joshi Krishna C. , Jain Renuka , Dandia Anshu , Garg Saroj , Ahmed Nidhal
Published: March 2009

A new spiroheterocyclic system spiro[9H‐acridine‐9,3′‐[3H]indol]‐2′(1′H)‐one and related compounds have been prepared by the reaction of spiro[3H‐indole‐3,9′‐[9H]xanthen]‐2(1H)‐ones with aromatic amine or ammonium acetate. The latter were prepared by heating fluorinated indole‐2,3‐diones with m‐/p‐cresols or α‐naphthol in the presence of sulphuric acid at 230‐240°. The synthesized compounds have been characterized on the basis of their elemental analyses, ir, nmr (1H, 13C, 19F) and mass spectral data.
Ring closure reactions of methyl N‐(haloacetyl)anthranilates with ammonia
Authors: Cho Nam Sook , Song Ki Youn , Párkányi Cyril
Published: March 2009

In the presence of ammonia, methyl N‐(bromoacetyl)anthranilate (4) is cyclized into 3H‐1,4‐benzodiaze‐pine‐2,5(1H,4H)‐dione (1). However, when 4 is replaced with methyl N‐(chloroacetyl)anthranilate (6), the only heterocyclic product formed in the reaction is 2‐(chloromethyl)quinazoline‐4(3H)‐one (7). Under analogous conditions, 3‐haloacetamidocrotonates (9, 10) do not yield any heterocyclic products and no 1,4‐diazepines can be obtained.
Synthetic approaches to hexahydropyrrolo[1,2‐b]isoquinolones
Authors: Smith Forrest T. , Deruiter Jack , Carter Deborah Ann
Published: March 2009

Synthetic routes to 1,2,3,5,10,10a‐hexahydropyrrolo[1,2,‐b]isoquinolin‐5‐ones functionalized at C‐10 were investigated. Attempts to prepare the ketone 2, and subsequently introduce the desired C‐10 hydroxymethylene group were unsuccessful due to the failure of 6 to cyclize and the unreactivity of 9 to relevant nucleophiles. Compound 1 was prepared by the condensation of 1‐pyrroline with 7‐methoxyisobenzopyran‐1,3,‐(4H)‐dione to give 12 in quantitative yield. Acyl halide formation and subsequent reduction gave the desired compound 1.
Synthesis of 6‐amino and 6‐ethoxy‐2(1H)‐pyridone derivatives
Authors: Cocco Maria Teresa , Congiu Cenzo , Maccioni Antonio , Plumitallo Antonio
Published: March 2009

An efficient route allowing the synthesis of 6‐amino and 6‐ethoxy‐2(1H)‐pyridone derivatives by reaction of ethyl cyanoacetimidate, ethyl ethoxycarbonylacetimidate and related acetamidines with diethyl ethoxymeth‐ylenemalonate (EMME) is reported. The formation of dienamino derivatives as intermediates and their heterocyclization to the 2(1H)‐pyridone derivatives is described.
A novel synthesis of 2‐vinylindoles and their utilization in the diels‐alder reaction for the formation of new [c] annellated carbazole derivatives
Authors: Akgün Eyup , Tunali Mustafa , Erdönmez Giray
Published: March 2009

A facile synthesis of 2‐vinylindoles is detailed, starting from the corresponding indolecarbinols. The utility of the newly synthesized 2‐vinylindoles in the preparation of novel [c] annellated carbazoles is demonstrated. 1‐(1‐Methyl‐2‐indolyl)‐1‐(N‐methyl‐2′‐pyrrolyl)ethene (3c) has also a 2‐vinylpyrrole partial structure. However, in the Diels‐Alder reaction of 3c, the exclusive formation of [c] annellated indoles was observed.
Epoxidation of 2‐azabicyclo[2.2.1]hept‐5‐en‐3‐one
Authors: Legraverend Michel , Bisagni Emile , Huel Christiane
Published: March 2009

Epoxidation of 2‐azabicyclo[2.2.1]hept‐5‐en‐3‐one has been performed in high yield with potassium hydrogen persulfate at pH 6, 1H nmr data indicate an exo stereoconfiguration of the epoxide.
A New synthesis of 4,5,6,7‐tetrahydrofuro[2,3‐c]pyridines and furo[2,3‐c]pyrrolidines
Authors: Arnoldi Anna , Bregante Giovanna , Caldirola Patrizia , Merlini Lucio , Tamburini Bruno
Published: March 2009

New syntheses of 4,5,6,7‐tetrahydrofuro[2,3‐c]pyridines and furo[2,3‐c]pyrrolidine derivatives, starting from furan‐3‐carboxaldehyde, are reported.