bluuebunny/crossref_metadata_2025_split huggingface dataset:
Synthesis of pyridine analogs of cumyl chloride‐2‐chloro‐2‐(pyridyl) propanes
Authors: Feuer Henry , Doty James K. 
Published: April 2009

AbstractChlorination of the isomeric isopropylpyridines with t‐butyl hypochlorite affords the tertiary α‐chloroalkylpyridines in good yield.
The reaction of 2,4‐diamino‐6‐piperidinopyrimidine 3‐oxide with acid anhydrides
Authors: Mccall John M. , Tenbrink Ruth E. , Royer Max E. , Ko Howard 
Published: April 2009

Abstract2,4‐Diamino‐6‐piperidinopyrimidine 3‐oxide reacts preferentially with acid anhydrides at the 4‐amino group. The structures of amide products are readily assigned by the position of the 5‐H.
Synthesis and reactivity with organometallic reagents of benzimidazole N‐oxides
Authors: Berti C. , Colonna M. , Greet L. , Marchetti L. 
Published: April 2009

AbstractAn easy synthesis of benzimidazole N‐oxides, and their reactivity with organometallic reagents to give stable nitroxide radicals, are described. 1‐Hydroxy‐2‐phenylbenzimidazole does not react in spite of its tautomeric equilibrium with the N‐oxide structure.
The contrasting behavior of cyclic and acyclic 2‐amidomethyleneresorcinols towards cyclization with acetaldehyde
Authors: Zaugg H. E. , Arendsen D. L. , Egan R. S. 
Published: April 2009

AbstractThe two cyclic amidomethylene resorcinols, 3a and 3b, readily undergo cyclization with acetaldehyde to the azacannabinoids 4 and 6, respectively. However, the acyclic amidomethylene resorcinol 10, under the same conditions, gives the benzodioxan 11. This contrasting behavior is rationalized in terms of conformational differences between 3a,b and 10.
Nitro group participation in the formation of heterocycles
Authors: Sunder Shyam , Peet Norton P. 
Published: April 2009

AbstractBenzoyl bromide (2‐nitrophenyl) hydrazone (2) was treated with sodium ethoxide and ethyl cyanoacetate and two unexpected products were obtained. These products were ultimately shown to be 6‐bromo‐3‐phenyl‐1,2,4‐benzotriazine (32) and 5‐bromo‐2‐phenylbenzoxazole (38), by comparison with authentic samples which were synthesized. A mechanism is presented for the formation of these two heterocyclic systems (32 and 38) from 2.
The kinetics of the reaction of some chloroisoxazolo[4.5‐c] and [5,4‐b] pyridines with methoxide ion
Authors: Adembri Giorgio , Ponticelli Alfredo Camparini Fabio , Tedeschi Piero 
Published: April 2009

AbstractArrhenius parameters were measured for the methoxy‐lechlorination reactions of some chloroderivatives of isoxazolo[4,5‐c]‐ and [5,4‐b]pyridine. A comparison of these results with the kinetic data for the corresponding chloropyridines shows that fusion of the isoxazole ring with the pyridine ring strongly increases the reactivity of the 4‐ and 6‐positions toward nucleophilic substitution.
Chemistry of the phenoxathiins VIII. Synthesis of 7‐chlorobenzo[1″.2″:5,6:3″,4″:5′,6′] bis[1,4] oxathiino[3,2‐b:3′.2′‐b′]dipyridine
Authors: Martin Gary E. , Turley James C. , Schram Karl H. 
Published: April 2009

AbstractAs a continuation of recent study on the synthesis of a bis[1,4]oxathiinodipyridine ring system, we would now like to report the preparation of 7‐chlorobenzo[1″,2″:5,6:3″,4″:5′,6′]‐bis[1,4]oxathiino[3,2‐b: 3′,2′‐b]dipyridine. Although a potentially complex reaction with several products possible, the title compound was formed exclusively, suggesting considerable mechanistic selectivity. The characterization of the product by FT‐1H‐nmr as well as its mass spectral fragmentation pathways are also reported.
Reactions with cyclic amidines II. The behaviour of cyclic amidines toward ethoxycarbonyl and aroyl isothiocyanates
Authors: Elnagdi Mohamed Hilmy , Fahmy Sherif Mahmoud , Elmoghayar Mohamed Rifaat Hamza , Kandeel Ezzat Mohamed 
Published: April 2009

AbstractThe behaviour of the aminopyrazole derivatives 1a‐c, 2‐amino‐4‐phenylthiazole (2) and 2‐amino‐5‐phenyl‐1,3,4‐thiadiazole (3) toward the action of ethoxycarbonyl and benzoyl iso‐thiocyanate is reported. The data clearly demonstrates the dependence of the nature of the products obtained from the reaction of isothiocyanates with cyclic amidines on the nature of the substituents on the heterocyclic ring.
Heterocycles from substituted amides. VI. A new carbostyril synthesis from alpha‐substituted acetamides and the vilsmeier reagent
Authors: Chupp John P. , Metz Suzanne 
Published: April 2009

AbstractReaction of tertiary α‐substituted acetanilides with Vilsmeier reagent has been found to give 1,3‐disubstituted‐carbostyrils, 1. α‐Chloro‐N‐(1‐cyclohexen‐1‐yl) acetamides are similarly converted to tetrahydro carbostyrils 2 and 3. The method appears useful for the preparation of a variety of 1,3‐substituted 2(1H) quinolinones. The scope and mechanism of the reaction has been investigated, with evidence presented to indicate the ring‐closure proceeds via electrophilic attack of Vilsmeier reagent on intermediate chlorenamine.
Synthesis of indazole C‐nueleosides and analogues
Authors: Alonso G. , Garcia‐Abbad E. , Garcia‐Lòpez M. T. , Stud M. 
Published: April 2009

Abstract1‐Deoxy‐1‐diazo‐3,6‐anhydro‐4,5,7‐tri‐O‐benzoyl‐D‐allo‐heptulosc (III) has been prepared from 2,5‐anhydro‐3,4,6‐tri‐O‐benzoyl‐D‐allonic acid. 1,3‐Dipolar cycloaddition of III to benzyne afforded the indazole C‐nucleoside analog V. Cycloaddition of methyl 6‐deoxy‐6‐diazo‐2,3‐O‐isopropylidene‐β‐D‐ribohexofuranosid‐5‐ulose (IV) to the benzyne generated from 5‐methyl‐anthranilic acid gave a mixture of the β‐isomeric C‐glycosylindazoles VI and VII along with traces of the corresponding α‐anomers VIa and VIIa. Finally, a multistep transformation of the acyclic carbohydrate moiety of 2,3,4,5‐tetra‐O‐acetyl‐1‐(indazol‐3‐yl)‐keto‐D‐ribopentulose (I, R = H, n = 3, D‐ribo) led to the C‐nucleoside indazole, 3‐(2,3‐O‐isopropylidene‐β‐D‐ribofuranosyl)‐indazol (X), as the major product.
Homolytic aromatic substitution of heterocyclic compounds. Part XIII. Arylation and heteroarylation of coumarin and benzo[b]furan using triazenes as the source of radicals. An experimental and theoretical study
Authors: Vernin Gaston , Coen Serge , Metzger Jacques , Párkányi Cyril 
Published: April 2009

AbstractThe homolytic arylation (substituents in the phenyl radical: none, p‐methyl, p‐fluoro, p‐chloro, p‐bromo, o‐chloro, 2,4‐dichloro, 3,5‐dichloro, 2,3,4‐trichloro, 2,3,5‐trichloro, o‐carbomethoxy, p‐carboethoxy, and o‐phenyl) and heteroarylation (2‐thiazolyl, 2‐benzothiazolyl, 3‐pyridyl) of coumarin and benzo[b] furan has been studied. The radicals were generated by thermal decomposition of the corresponding 1,3‐diaryltriazenes in the presence of isoamyl nitrite. Homolytic substitution of coumarin takes place exclusively in the position 3, in agreement with the prediction based on SCF‐MO free valences. In the case of benzo[b]furan, all the reactivity indices (F, Sr, and Ar) predict the position 2 to be most reactive, in agreement with the experimental results. Comparison of the mass spectra of the products indicates similarities between the spectra of arylcoumarins and arylbenzo[b]furans and the existence of a common intermediate in their fragmentation pattern, viz., the benzo[b]furan cation radical.One of the authors (G.V.) wishes to thank Prof. A. Maquestiau (Mons, Belgium) for useful suggestions concerning mass spectrometry. One of the authors (CP.) should like to thank the Ministere de l'Education Nationale, le Secretariat d Etat aux Universités, Paris, for a visiting professorship, and the National Science Foundation, Washington, D. C. for a travel grant. Also, the authors wish to express thanks to Mrs. G. Vernin for her careful technical assistance.
Synthèse de nouveaux alkyl‐2 et ‐3 tétrahydrofurannes et ‐pyrannes
Authors: Montaudon E. , Thèpénier J. , Lalande R. 
Published: April 2009

AbstractDe nouveaux alkyl‐2 et ‐3 tétrahydrofurannes et ‐pyrannes possédant ou non une ramification sur le carbone 1 de la chaǐne latérale sont synthétisés et décrits. Les préparations proposées sont généralisables. Parmi les composes connus de ce type, très rares sont ceux dont le carbone 1 de la chame latérale est tertiaire ou quaternaire.
N‐acyl‐N‐formylcarbamates. A new class of carbamate derivatives
Authors: Graziano M. L. , Iesce M. R. , Scarpalixs R. 
Published: April 2009

AbstractN‐Acyl‐N‐formylcarbamates III can be prepared in good yields by singlet oxygen oxidation of 5‐unsubstituted 4‐alkoxyoxazoles I. They are photo‐ and thermo‐stable and sensitive to hydrolysis under very mild conditions. In contrast 4‐unsubstituted 5‐alkoxyoxazole V reacts with singlet oxygen to give oxamate VII via dioxazole VI.
Nitrogen bridgehead compounds VIII . Ring transformations IV . Synthesis and reactions of 2,3‐Cycloalkylene‐4H‐pyrido [1,2‐a] pyrimidin‐4‐ones
Authors: Bernàth G. , Fülöp F. , Hermecz I. , Mészáros Z. , Tóth G. 
Published: April 2009

AbstractBy condensing alicyclic β‐ketocarboxylates with substituted 2‐aminopyridines in polyphosphoric acid or phosphoryl chloride‐polyphosphoric acid, numerous 2,3‐tri‐, tetra‐, penta‐ and hexamethylene‐4H‐pvrido[1,2‐a]pyrimidin‐4‐ones were synthesized for pharmacological purposes. The stability and several reactions of the title compounds were studied. The 6‐substituted‐4H‐pyrido[1,2‐a]pyrimidin‐4‐ones were transformed into 1,8‐naphthyridines in good yields independent of the ring size of ring C. The characteristic differences in the ir and uv spectra of the pyrido‐pyrimidines and the corresponding naphthyridines are discussed. Catalytic hydrogenation of the pyrido[1,2‐a]pyrimidin‐4‐ones furnished the corresponding 6,7,8,9‐tetrahydropyrido‐[1,2‐a]pyrimidin‐4‐one derivatives. It was found that the A and C rings attached to the pyrirnidinone ring in solutions of unsubstituted tetrahydropyrido[1,2‐a]pyrimidin‐4‐ones are flexible, whereas in the 6‐methyl derivatives the conformer containing the 6‐methyl group in axial position predominates.
An improved procedure for the preparation of 9‐β‐D‐Arabitiofuranosyl‐2‐ñuoroadenine
Authors: Montgomery John A. , Clayton Sarah D. , Shortnacv Anita T. 
Published: April 2009

AbstractAn improved procedure for the preparation of 9‐β‐D‐arabinofuranosyl‐2‐fluoroadenitie (11) utilizing the readily available 2,4,5,6‐tetraaminopyrimidine (1) is described; the overall yield based on the arabinosugar was quadrupled.
Synthesis of some 3‐substituted quino[3,2‐c][1,8]naphtyridines. A new heterocyclic ring system
Authors: da Settimo Antonio , Prirnofiore Giampaolo , Livi Oreste , Ferrarini Pier Luigi , Spinelli Silvano 
Published: April 2009

AbstractIsatoic acid reacts with 7‐mcthyl‐2,3‐dihydro‐1,8‐naphthyridin‐4(1H) one (8) to give 3‐methyl‐5,6‐dihvdroquino[3,2‐c][1,8]naphthyriclin‐7‐carboxylic acid (9a), which was transformed into the 3‐methylquino[3,2‐c][1,8]naphthyridine (7a) by refluxing with copper chromite in quinoline. The same product (7a) was also obtained by aromatization of the 3‐methyl‐5,6‐dihydroquino‐[3,2‐c][1.8]naphthvridine (10a), prepared by condensation of the ketone (8) and o‐aminobenzaldehyde. Other 3‐substituted quino[3,2‐c][1,8]naphthyridines (7b,c,d,e), which contain a new heterocyclic, ring structure, have been prepared using o‐aminobenzaldehyde and 7‐sub‐stituted‐2,3‐dihv dro‐1,8‐naphthyridin‐4(1H) ones (12 and 13) as starting materials. Also, the preparation of the parent nucleus (7f) is described.
Synthesis of 5‐methyl‐1,3,2‐benzodithiazoles
Authors: Chen Chin H. , Donatelli Barbara A. 
Published: April 2009

AbstractThe novel helerocycles 5‐methyl‐1,3,2‐benzodithiazoles (7) were prepared in 30–50% yields from toluene‐3,4‐dithiol (6) and appropriate primary amines in the presence of 2 equivalents of triethylamine under high‐dilution conditions. These compounds, which exhibit one reversible oxidation potential around +0.90 V vs. SCE, serve as a model study in the quest of synthesizing a new donor, the “boron‐nitrogen” analog of tetrathiafulvalene (BNTTF).
A general synthesis of alkyl 6‐substituted‐pyrazolo‐[3,2‐c] ‐s‐triazolo‐7‐carboxylates
Authors: Stanovnik Branko , Tišler Miha , Kirn Branko , Kovač Igor 
Published: April 2009

AbstractA general synthesis of alkyl 6‐methyl‐ and 6‐phenylpyrazolo[3,2‐c]‐s‐triazolo‐7‐carboxylates by photochemical Wolf rearrangement of 6‐methyl‐ and 6‐phenyl‐7‐diazo‐8‐oxo‐s‐triazolo‐[4,3‐b]pyridazine in an alcohol is described.
Tricyclic chemistry. Synthesis and chemistry of a novel polyheterocycle
Authors: Rokach J. , Girard Y. , Atkinson J. G. , Rooney C. S. 
Published: April 2009

AbstractThe photochemical reaction of 1 with acrylonitrile gave the cyclobutane adducts II and III, which on treatment with base afforded a novel polycyclic structure IV. Reduction of IV with LAH followed by Eschweiler‐Clarke methylation yielded the polyheterocyclic structure VI.
Photochemical reactions of 3‐methyl‐4‐nilro‐5‐styrylisoxazole in solution, in the solid slate and adsorbed on silica gel
Authors: Donati D. , Fiorenza M. , Sarti‐Fantoni P. 
Published: April 2009

AbstractThe pholoreactivity of 3‐melhyl‐4‐nitro‐5‐styrylisoxazole in solution and adsorbed on silica gel was studied and the photodimers obtained were identified. The structures of the pholoproduels were assigned on the basis of mass and nmr spectra and chemical behavior. Irradiation of the title compound adsorbed on solid or slurry silica gel leads to the same photoproducts obtained from the solution but with a different yield.
Synthesis of two novel bicyelic systems, imidazo[1,5‐D]‐as‐triazine and imidazo[1,2‐d]‐as‐triazine
Authors: Paul Rolf , Menschik Judith 
Published: April 2009

Abstract4‐Imidazolecarboxyaldehyde was condensed with methyl dithiocarbazinate and with ethyl carbazate, the resulting hydrazones were subjected to thermolysis in diphenyl ether at 175–240, to give imidazo[1,5‐d]‐as‐triazine‐4(3H)thione and imidazo[1,5‐d]‐as‐triazin‐4(3H)one, respectively. A number of 2‐, 5‐, and 2,5‐substituted 4‐imidazolecarboxaldehydes were also carried through this scheme. The same sequence of reactions with 2‐imidazolecarboxaldehyde gave the novel system imidazo[1,2‐d]‐αs‐triazine‐5‐(6H)‐thione. Upon treatment with sodium hydride and methyl iodide, imidazo[1,5‐d]‐as‐triazine‐4(3H)thione and imidazo[1,2‐d]‐as‐triazine‐5(6H)‐thione gave 4‐methylthioimidazo[1,5‐d]‐as‐triazine and 5‐methylthioimidazo[1,2‐d]‐as‐triazine, respectively. Displacement of the thiomethyl group was achieved with a selection of amine reagents in both of the above cases.
Heterocyclic compounds. XI. Potential post‐coital antifertility agents
Authors: Manhas M. S. , Amin S. G. , Sharma S. D. , Dayal B. , Bose Ajay K. 
Published: April 2009

AbstractA series of heterocyclic analogs of diarylethylene and triarylethylene were synthesized as potential anti‐implantation agents. Tested in rats as oral, post‐coital antifertilily agents, a few of our compounds showed some activity.
1,3‐Dipolar cycloadditions. Reactions of nitrile imines with 1,2‐disubstituted alkenes
Authors: Chiericato Marco , Dalla Croce Piero , Carganico Germano , Maiorana Stefano 
Published: April 2009

AbstractNitrile imines react with 1‐phenylsulphonyl‐2‐benzoyl (or methoxycarbonyl)alkenes to give 4‐phenylsulphonyl‐5‐benzoyl (or methoxycarbonyl) substituted pyrazolines. The cycloaddition regioselectivity is discussed in terms of Frontier Orbital energies and coefficients.
Acid‐catalyzed rearrangements of 6‐(p‐tolyhydrazino)‐2‐thiouraeil
Authors: Wright G. E. , Gambino J. 
Published: April 2009

AbstractThe action of acid on 6‐(p‐tolylhydrazino)‐2‐thiouracil gives appreciable amounts of the stable Fischer intermediate, 5‐(2 ‐amino‐5 ‐tolyl)‐6‐amino‐2‐thiouracil. This compound undergoes intramolecular cyclization at high temperatures, and represents the first reported isolation of a diamine intermediate derived from a Fischer‐type indolization reaction.
Chemical conversion of uridine to 8,5′‐O‐cyclo‐3‐deazaguanosine
Authors: Tanaka Hiromichi , Veda Tohru 
Published: April 2009

AbstractTreatment of 1‐(2,3‐O‐isopropy lidene‐β‐D‐ribofuranosyl)‐2‐oxo‐4‐imidazoline‐4‐carboxylic acid methyl ester with formaldehyde gave the 5‐hydroxymethyl derivative which, after aeetylalion, gave the 5‐eyanomelhyl derivative by treatment with tetra‐n‐butylammonium cyanide. The 2,5′‐O‐cyclo derivative of the 5‐cyanomethylimidazole‐4‐carboxylate was converted to the title compound by treatment with ammonia. The present sequence of reactions furnished the chemical conversion of uridine to a 3‐deazaguanosine via the imidazole nucleoside as the intermediate.
The chemistry of 2H‐3,1‐benzoxazine‐2,4‐(1H)dione (isatoic anhydride) 3. One step synthesis of 2,3‐dihydro‐4,1,6‐benzoxadiazonine‐5,7‐(1H,6H)diones
Authors: Barcza Sandor , Coppola Gary M. , Shapiro Michael J. 
Published: April 2009

AbstractReactions of N‐haloalkylisatoic anhydrides with amines to produce piperidinobenzamides (2), pyrrolidinobenzamides (4 and 5), and 2,3‐dihydro‐6‐methyl‐4,1,6‐benzoxadiazonine‐5,7‐(1H,6H)diones (10) are described. Spectral data are also discussed.
Polymorphic behavior and melting points of certain benzocrown ether compounds
Authors: Stott Paul E. , Mccausland Calvin W. , Parish W. Wesley 
Published: April 2009

AbstractFreshly prepared samples of dibenzo‐24‐crown‐8 and 4‐t‐butylbenzo‐15‐crown‐5 were found to have melting points which varied significantly from those origionally reported in the scientific literature. Samples prepared for the origional report were obtained, and were compared with the new samples. The origional report was found to be in error and the corrected values are provided. Dibenzo‐24‐crown‐8 was found to exist as at least three polymorphs. One of these is a glass. The other two are crystalline, but have identical melting points. It was discovered that the less stable form is thermally converted to the more stable form at temperatures below its melting point.
Alkyl nitrate nitration of active methylene compounds. Nitration of 1‐methyl4‐piperidone, 1‐methyl‐2‐pyrrolidinone and 1,3‐dimethyl‐2‐pyrrolidinone
Authors: Feuer Henry , Blecker Lamarr R. , Jans Robert W. , Frost John W. 
Published: April 2009

AbstractThe reaction of 1‐methyl‐4‐piperidone (1) with amyl nitrate in the potassium tert‐butoxidetetrahydrofuran system gave dipotassium 5‐methyl‐2‐oxo‐1,3‐piperidinedinitronate (4) in 78% yield. Similar treatment of 1‐methyl‐2‐pyrrolidinone (2) afforded potassium 3‐methyl‐2‐oxopyrrolidinenitronate (7) in 85% yield. In contrast, the nitration of 1,3‐dimethyl‐2‐pyrrolidinone (3) led to opening of the lactam ring with the formation of amyl 2‐aza‐2‐methyl‐5‐nitrohexanoate (10) in 40% yield.Acidification of disalt 4 did not cause ring opening but gave the dipolar ion of 1‐methyl‐3‐nitro 4‐hydroxy‐5‐aci‐nitro‐Δ3‐tetrahydropyridinium (6).
Thiazolidinone arylhydrazones. Ring cleavage and alkylation of the 5‐arylhydrazone derivatives of rhodanine and isorhodanine
Authors: Kassab Nazmi A. , Abd Allah Sanaa O. , Elbahaii Said A. 
Published: April 2009

AbstractThe 5‐aryihydrazone derivatives of rhodanine and isorhodanine were subjected to the action of hydrazine hydrate to afford the arylhydrazonomercaptomethyltriazolinthione and ‐triazolinone derivatives 3 and 4, respectively. Treatment of 1 with benzylamine afforded thioxalic acid dibenzylamide 5. On the other hand, treatment of 2 with the same reagent afforded the corresponding benzylamino derivatives 6. Alkylation of 1 and 2 with ethyl bromoacetate and chloroacetamide yielded the corresponding S‐alkyl derivatives 7 and 8, respectively.
Synthesis in the diazasteroid group X. A synthesis of 8,12‐diaza‐D‐homosteroid
Authors: Yamazaki Takao , Takahata Hiroki , Hama Yoko , Takano Yoshiaki , Nagata Masanori , Castle Raymond N. 
Published: April 2009

AbstractThe condensation of 1‐aminoethyl‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline 1 with 1,2‐cyclohexanedione 2 gave the 8,12‐diaza‐D‐homosteroid system 3, which was reduced with Adams' catalyst followed by acetic anhydride acetylation to afford the 8,12‐diaza‐D‐homosteroids 4a,b.
Synthesis of 1,3‐disubstituted hydantoins as possible anticonvulsants
Authors: Joshi Puran C. , Parmar Surendra S. , Rastogi Vinai K. 
Published: April 2009

AbstractSeven newer 1,3‐disubstituted hydantoins (17–23) were synthesized from 4‐alkoxyanilines. The anticonvulsant activity of these substituted hydantoins and their precursor carbamides (10–16) was reflected by their ability to provide 28–80% and 30–70% protection, respectively, against pentylenetetrazol‐induced convulsions in mice. In general, substituted hydantoins possessed greater anticonvulsant activity than their corresponding precursor carbamides.
Assignments of the chemical shifts of carbon‐13 nuclear magnetic resonance spectra of some 2‐methyl‐3‐(3,4‐dimethoxy/dihydroxyphenylethyl)‐4‐quinazolones
Authors: Singh Shiva P. , Parmar Surendra S. , Farnum Sylvia A. 
Published: April 2009

AbstractThe 13C nmr chemical shifts of a series of 2‐methyl‐3‐(3,4‐dimethoxy/dihydroxyphenylethyl)‐4‐quinazolones are reported. The carbon resonances have been assigned on the basis of chemical shift theory, intensity of the signals, multiplicities generated in SFORD spectra and the comparison with the structurally related compounds.
Chemistry of benzo[b]furan. V.. Synthesis of substituted thia‐analogs and oxa‐analogs of dihydrorutecarpine and evodiamine
Authors: Shafiee A. , Mohammadpour‐Toiserkani M. 
Published: April 2009

AbstractCycloaddition of 3,4‐dihydrobenzo[b]thieno[2,3‐c]pyridine (6) with the sulfinamide anhydride 9 (R = H) afforded the thia‐analog of dihydrorutecarpine (2a). Condensation of the imine 6 with the sulfinamide anhydride 9 (R = CH3) gave the thia‐analog of evodiamine (2b). Starting from 1‐methyl‐3,4‐dihydrobenzo[b]thieno[2,3‐c]pyridine (12) and 1‐methyl‐3,4‐dihydrobenzo[b]furo[2,3‐c]pyridine (14), a series of 3‐methyl derivatives of thia‐analogs of dihydrorutecarpine and evodiamine (2c‐2i) and oxa‐analogs of dihydrorutecarpine and evodiamine (1a‐1g) were similarly prepared.
Diazo‐, azo‐, and azidoazoles. V. MNDO calculations on the 2‐azidoimidazole/imidazo[1, 2‐d]tetrazole equilibrium
Authors: Olivella Santiago , Vilarrasa Jaume 
Published: April 2009

AbstractCalculations are reported for the cyclization of 2‐azidoimidazole and its anion to the corresponding pentaazapentalenes using the recently developed MNDO semiempirical SCF‐MO method. The bicyclic anion is predicted to be 16.9 kcal/mole relatively more stable than the neutral bicyclic molecule. The shifting of the equilibrium to the tetrazole form in the case of the anion is mainly attributed to the dercalization of the negative charge on the tetrazole moiety of the bicyclic system.
Stereospecific synthesis and carbon‐13 nmr spectra of 1,4‐epoxydecahydronaphthalenes
Authors: Rose Charles B. , Taylor Stephen K. 
Published: April 2009

AbstractThe stereoselective synthesis of cis‐fused 1,4‐epoxydecahydronaphthalenes from transannular reactions of medium‐ring compounds is described. The carbon‐13 nmr spectra of both are reported, and assignments of the various resonances have been made based on model compounds and off‐resonance decoupling experiments.
Polyazasteroids II.. 1,2,4‐Triazolol[3′,4′:2,3]pyrimido[4,5‐c]quinolin‐ 11(12H)ones, imidazo[2′,1′:2,3]pyrimido[4,5‐c]quinolin‐11(12H)ones and 2,3‐dihydroimidazo[2′,1′:2,3] pyrimido[4,5‐c]quinolin‐11(12H)ones
Authors: Lalezari I. , Sadeghi‐Milani S. 
Published: April 2009

AbstractStarting with 2‐substituted quinoline‐3,4‐dicarboxylic acids, a series of substituted 1,2,3,4‐tetrahydropyrimido[4,5‐c]quinolinone‐3‐thiones were obtained. The latter compounds were converted to the three novel polyazasteroid series: 1,2,4‐Triazolo[3′,4′:2,3]pyrimido[4,5‐c]‐quinolin‐11(12H)ones, imidazo[2′,1′:2,3]pyrimido[4,5c]quinolin‐11(12H)ones and 2,3‐dihydroimidazo[2′,1′:2,3]pyrimido[4,5‐c]quinolin‐11(12H)ones. The intermediate 3‐hydrazino‐1,2‐dihydropyrimido[4,5‐c]quinolinones and nitrous acid gave the 3‐azido derivatives rather than the tetrazolo compounds.
Reaction of tetraoxopyrrolo [2,3‐d] pyrimidines, isatin analogues, with o‐phenylenediamine
Authors: Bernier Jean‐Luc , Hénichart Jean‐Pierre 
Published: April 2009

AbstractIn the course of general studies on new antitumor tetracyclic intercalating agents, the condensation of o‐phenylenediamine with two new tetraoxopyrrolo[2,3‐d]pyrimidine derivatives has been carried out. The structure of the reaction products as arylketimines has been elucidated and mass spectral fragmentations are discussed.