bluuebunny/crossref_metadata_2025 huggingface dataset:
A synthesis of 6,11‐dihydro‐2‐methyl‐6H‐pyrimido[2,1‐b]quinazolin‐4‐ones
Authors: Friary R.
Published: April 2009

Reductive cyclization of 2‐methylthio‐1‐(2‐nitrobenzyl)‐6‐pyrimidones with stannous chloride and acetic acid in methanol gives 6,11‐dihydro‐6H‐pyrimido[2,1‐b]quinazolin‐4‐ones, and, with trialkylphosphites, 6,11‐dihydro‐11‐alkylpyrimido[2,1‐b]quinazolin‐4‐ones.
Bromine‐induced cyclization of 1‐acyl‐3‐(3‐thienyl)‐2‐thioureas to 2‐acylaminothieno[3,2‐d]thiazoles
Authors: Grehn Leif
Published: April 2009

Three different 1‐acyl‐3‐(3‐thienyl)‐2‐thioureas were cyclized to 2‐acylaminothieno[3,2‐d]thiazoles with bromine in acetic acid whereas the corresponding 2‐thienylthiourea derivatives were brominated under the same reaction conditions. The parent thieno[3,2‐d]thiazole was prepared by acid hydrolysis and deamination of 2‐benzoylaminothieno[3,2‐d]thiazole. This new heterocyclic compound was nitrated and brominated in the 5‐position.
N‐Vinyl as N‐H protecting group. Synthesis of cyclic imines from N‐vinyllactams and organolithium reagents
Authors: Bielawski Jacek , Brandänge Svante , Lindblom Lars
Published: April 2009

On reaction with organolithium reagents followed by hydrolysis and distillation, N‐vinylpyrrolidone (1) gives five‐membered ring imines 3‐8, whereas N‐vinylcaprolactam (2) gives mixtures of seven‐membered ring imines and the corresponding ∈‐amino ketones.
Synthesis via pummerer intermediates. III. Rearrangements of 3‐(methylsulfinyl)quinolinones, 3‐(methylsulfinyl)cinnolinones, 3‐(methylsulfinyl)chromanones and 3‐(methylsulfinyl)chromones with acetic anhydride and with thionyl chloride
Authors: Connor David T. , Young Patricia A. , von Strandtmann Maximillian
Published: April 2009

The reaction of 1‐methyl‐3‐(methylsulfinyl)‐4(1H)quinolinone (1) with acetic anhydride and thionyl chloride gave 3‐[[(acetyloxy)methyl]thio]]‐1‐methyl‐4(1H)quinolinone (2) and 3‐[(chloromethyl)thio]‐1‐methyl‐4(1H)quinolinone (3) respectively. 3‐(Methylsulfinyl)‐4(1H)cinnolinone (4) gave the corresponding products when treated under similar conditions. Treatment of 8‐methoxy‐3‐(methylsulfinyl)‐4H‐1‐benzopyran‐4‐one (11) with acetic anhydride and thionyl chloride gave bis addition vinyl Pummerer products 2,3‐bis(acetyloxy)‐2,3‐dihydro‐8‐methoxy‐3‐(methylthio)‐4H‐1‐benzopyran‐4‐one (12) and 2,3‐dichloro‐2,3‐dihydro‐8‐methoxy‐3‐(methylthio)‐4H‐1‐benzopyran‐4‐one (13), respectively.
Synthesis of an imidazo[1,2‐c]pyrimidine analog of a thiamine antagonist coccidiostat and a comparison of several methods for the preparation of imidazo[1,2‐c]pyrimidines
Authors: Kluge Arthur F.
Published: April 2009

Several methods for the preparation of imidazo[1,2‐c]pyrimidines are presented. Compound 12 was prepared from 11 and chloroacetaldehyde in water using a buffer to control pH. Compound 12 was converted in two steps to 14, the etheno bridged analog of the coccidiostat 1. Several methods were used to prepare 8‐phenylimidazo[1,2‐c]pyrimidine (16). In terms of yield the best method was the reaction of the aminopyrimidine 15 with chloroacetaldehyde in acetone and in the presence of calcium carbonate as an acid scavenger. Reaction of the 4‐chloro‐pyrimidine 19 with aminoacetaldehyde diethyl acetal gave 16 directly in modest yield.
The synthesis of the 1‐ and 2‐cycloalkyl‐1,2,3‐benzotriazole system
Authors: Serve' M. Paul , Seybold P. G. , Covault H. Patrick
Published: April 2009

The first reported synthesis of 1‐ and 2‐cycloalkyl‐1,2,3‐benzotriazoles is reported. Physical and spectral data of the system are reported. Molecular orbital calculations on the 1,2,3‐benzotriazole anion show that N1 is a more nucleophilic site than N2.
The mass spectrometric fragmentation of selenophene and tellurophene
Authors: Fringuelli F. , Taticchi A.
Published: April 2009

The mass spectra of selenophene and tellurophene have been measured and their modes of fragmentation compared with those of furan and thiophene.
Synthesis of 3‐N‐acetyl‐N‐arylaminoacetyl‐4‐ethoxycarbonyl‐5‐methylpyrazoles
Authors: Chantegrel Bernard , Gelin Suzanne
Published: April 2009

The acetylation of 2‐N‐arylaminomethylene‐4‐ethoxycarbonyl(or acetyl)‐5‐melhyl‐3(2H)furan‐ones produces N‐acetylated compounds which react with hydrazine to yield substituted pyrazoles.
Condensed benzopyrans II. Some derivatives of 3H‐pyrano[3,2‐f]quinoline
Authors: Khan Misbahul Ain , Gemal André Luis
Published: April 2009

The reaction of 6‐aminoeoumarin with some ethoxymethylene compounds and dimethyl acetylenedicarboxylate led to condensation products which on thermal cyclizations afford new derivatives of 3H‐pyrano[3,2‐f]quinoline (IIa‐IIc).
The synthesis of 7,8‐dihydroimidazo[1,2‐e]pyrazolo[1,5‐a]‐1,3,5‐triazines, 8,9‐dihydro‐7H‐pyrimido[1,2‐e]pyrazolo[1,5‐a]‐1,3,5‐triazines and 7,8,9,10‐tetrahydro[1,3]diazepino[1,2‐e]pyrazolo[1,5‐a]triazines
Authors: Lalezari I. , Sadeghi‐Milani S.
Published: April 2009

Cyclic hydrazino amidines were converted to the corresponding aminopyrazolyl derivatives. Ring closure between the amino groups of pyrazoline moieties and NH groups of cyclic amidines afforded the following ring systems: 7,8‐Dihydroimidazo[1,2‐e]pyrazolo[1,5‐a]‐1,3,5‐triazines, 8,9‐dihydro‐7H‐pyrimido[1,2‐e]pyrazolo[1,5‐a]‐1,3,5‐triazines and 7,8,9,10‐tetrahydro[1,3]diazepino[1,2‐e]pyrazolo[1,5‐a]‐1,3,5‐triazines.
Potential histidine decarboxylase inhibitors. II. 3‐(4‐Imidazolyl)‐2‐pyridine and piperidinecarboxylates
Authors: Degraw J. I. , Engstrom J. S. , Ellis M. , Johnson H. L.
Published: April 2009

The synthesis of methyl 3‐(4‐imidazolyl)‐2‐pyridine (12) and piperidineearboxylates (13) is described. Hydrolysates of these esters were found to be devoid of inhibitory activity against histidine decarboxylase. 3‐Bromoacetyl‐2‐pieoline (2) could be converted to 3‐(4‐imidazolyl)‐2‐picoline (6) by two different routes. Treatment of 6 with peroxide and acetic anhydride, followed by transesterification yielded the 2‐hydroxymcthyl pyridine (9). Oxidation of 9 followed by esterification gave the imidazole pyridine acid ester (12) which after hydrogenation afforded the imidazolylpiperidine ester (13).
The resolution of an optically active pyridinethiol
Authors: Mulvey Dennis M. , Jones Howard
Published: April 2009

The resolution of a chiral pyridine thiol has been eonveniently carried out through derivatives with optically active α‐phenethylisoeyanates. Optically active heterocyclic thiols in which the thiol occupies the center of chirality are not known in the literature. In conjunction with a synthetic program dealing with derivatives and analogues of 5‐mercaptopyridoxine (1), the preparation of such species was accomplished. Their resolution proved to be difficult, but the techniques devised herein should prove of general utility for other heteroeyclic thiols or alcohols.
Tetrahydropyridoazepines and tetrahydropyridoazepinones from the corresponding dihydroquinolones
Authors: Jössang‐Yanagida Akino , Gansser Charles
Published: April 2009

The p‐toluenesulfonate of 7,8‐dihydro‐5(6H)quinoloneoxime(3) was subjected of a Beckmann rearràngement. The resulting 2,3,4,5‐tetrahydro‐1H‐pyrido[3,2‐b]azepin‐2‐one (4) was reduced with lithium aluminum hydride affording 2,3,4,5‐tetrahydro‐1H‐pyrido[3,2‐b] azepine (5). 5,6‐l)ihydro‐8(7H)quinolone (7), obtained by oxidation of 5,6,7,8‐tetrahydro‐8‐quinolinol (6), was converted into the p‐toluenesulfonate of 5,6‐dihydro‐8(7H)quinolone oxitne (9). Similarly the latter compound could be rearranged into 2,3,4,5‐letrahydro‐1H‐pyrido [2,3‐b] azepin‐2‐one (10) which on reduction produced 2,3,4,5‐tetrahydro‐1H‐pyrido [2,3‐b] azepine (11).
Perhydroisoindoliniums et perhydroisoquinoliniums: Préparation et étude stéréochimique
Authors: Mayrargue Joëlle , D'Engenières Michel Duchon , Miocque Marcel
Published: April 2009

Les éthynylcyclohexanols aminométhylés en position 2 se cyclisent en présence d'eau pour former des perhydroisoindoliniums; les propynylcyclohexanols homologues eonduisent à des perhydroisoquinoliniums.

Les diastéréoisomères ont été isolés. Leur stéréochimie est étudiée par spectrographie (1H rmn et 13C rmn): elle met en évidence une stéréopréférence pouvant aller jusqu' à la sélectivité complète lors de la cyclisation des aminocyclohexanols acétyléniques à l'état de mélanges de diastéréoisomères (obtention exclusive d'hétérocycles à jonction trans).
Synthesis and stereochemical analysis of isomeric N‐substituted 5‐ and 6‐propanilido‐2‐azabicyclo[2.2.2]octanes
Authors: Law Say‐Jong , Lewis Daniel H. , Borne Ronald F.
Published: April 2009

The synthesis and stereochemical analysis of N‐methyl and N‐phenethyl‐substituted 5‐ and 6‐propanilido derivatives of 2‐azabicyclo[2.2.2]octane were investigated for potential evaluation as analgesics related to fentanyl. Stereochemical assignments for the eight isomers reported here were made on the basis of nmr studies employing europium chemical shift reagents and hydrogen bonding studies employing ir analysis of the anilino‐ and propanilido‐derivatives.
The insertion and extrusion of heterosulfur bridges. VI. Comparative desulfurizations of dibenzothiophene and biphenylthiols
Authors: Klemm L. H. , Karchesy Joseph J.
Published: April 2009

Products were determined from reaction of biphenyl‐2‐thiol (5) with methanol in a packed flow reactor at elevated temperatures and ca. atmospheric pressure. At 450–550° thermolysis of 5 gives small yields of dibenzothiophene (1) and biphenyl (2). With sulfided alumina, products vary with reaction temperature from 82% S‐methyl‐5 at 250° to only 1 plus 2 at 550°. At 450° with sulfided cobaltous oxide‐molybdic oxide‐aluminum oxide (CMA‐1), 5 and its isomers give mainly desulfurization to 2 (81%), plus C‐melhylalion to melhylbiphenyls and fluorene. With CMA‐1 at 450° the arrays of products from 1 and 5 are closely similar.
Addition reactions of heterocycles. VI. Reactions of 1,2‐dimethylpyrrole and 1‐methyl‐2‐carbomethoxypyrrole with nitrilimines
Authors: Ruccia Michele , Vivona Nicolò , Cusmano Giuseppe
Published: April 2009

Addition reactions of 1,2‐dimethylpyrrole and 1‐methyl‐2‐carbomethoxypyrrole with C‐acetyl‐N‐phenylnitrilimine, have been investigated. 1,2‐Dimethylpyrrole gives three different types of adducts: i.e. bis‐cycloadducts (Vc) and (VIc), spirocycloadduct (IX), and non cyclic bis‐adduct (XII). On the other hand, 1‐methyl‐2‐carbomethoxypyrrole gives the bis‐cycloadduct (VIb) only. Compound XII arises probably through a double 1,3‐addition reaction, whereas the formation of cycloadducts Vc, VIc, and IX depends on the substituents present at C2 of the pyrrole ring and consequentially on the intermediary occurence of mono‐cycloadduct (IIIc), its methylenic tautomer VII, VIc, and XL The behaviour of the cycloadducts towards heating or acidic treatment showed a termal cleavage of the pyrazoline ring and acidic cleavage of the pyrrolidine ring.
A base induced fragmentation of tetramisole
Authors: Fibiger Richard F. , Banks Allen R. , Jones Ted , Haltiwanger R. Curtis , Watt David S.
Published: April 2009

The exposure of dl‐2,3,5,6‐tetrahydro‐6‐phenylimidazo[2,1‐6 Jthiazole (tetramisole) to lithium diisopropylamide in tetrahydrofuran ruptures the thiazole ring to give, following the introduction of primary or secondary alkyl halides, 1‐(2′‐alkylthio)ethyl‐4‐phenylimidazoles. Conclusive evidence for the thiazole ring opening was obtained by a single crystal x‐ray diffraction study of 1‐(2′‐p‐bromobenzylthio)ethyl‐4‐phenylimidazole.
Pyrazolo[3,4‐b]pyridines. I. Xanthine and isoguanine analogs derived from 1‐methylpyrazolo[3,4‐b]pyridine
Authors: Schneller S. W. , Moore D. R.
Published: April 2009

The synthesis of 4,6‐dihydroxy‐l‐methylpyrazolo[3,4‐b Jpyridine (2) and 4‐amino‐6‐hydroxy‐1‐methylpyrazolo[3,4‐b] pyridine (3) as analogs of xanthine and isoguanine has been accomplished from ethyl 5‐amino‐1‐methylpyrazole‐4‐carboxylate (4) and 5‐amino‐1‐methylpyrazole‐4‐carbo‐nitrile (6), respectively.
Steric controls in the preparation of 1‐benzyl‐1,4‐dihydro‐3‐(2H)isoquinolones and 1‐benzyl‐1,2,4,5‐tetrahydro(3H)‐2‐benzazepin‐3‐ones via Beckmann rearrangement
Authors: Jensen Bruce L. , Michaud Dennis P.
Published: April 2009

The effect of substituents in the 1‐position of 2‐indanones and 2‐tetralones on the course of Beckmann rearrangement reactions was studied. Nmr spectral anaylses of the intermediate oximes and final products demonstrated that steric controls were operative both before and during rearrangement. Use of the appropriate substituents and reaction conditions makes this reaction scheme attractive for preparation of the title compounds.
Chlorination of 1H‐pyrrolo[3,2‐c]pyridin‐4,6(5H,7H)dione (3,7‐dideazaxanthine) and its 5‐methyl derivative
Authors: Schneller S. W. , Hosmane R. S.
Published: April 2009

The chlorination of 1H‐pyrrolo[3,2‐c]pyridin‐4,6(5H, 7H)dione (3,7‐dideazaxanthine) (2) and 5‐methyl‐1H‐pyrrolo[3,2‐c] pyridin4,6(5H,7H)dione (1 ‐methyl‐3,7‐dideazaxanthine) (3) with phenylphosphonic dichloride has yielded 4,6‐dichloro‐1H‐pyrrolo[3,2‐c]pyridine (2,6‐dichloro‐3,7‐dideazapurine) (1). A mechanism for the demethylation of the 5‐methyl derivative under these conditions is proposed. Ammonolysis of 4,6‐dichloro‐1H‐pyrrolo[3,2‐c] pyridine was unsuccessful while catalytic reduction of this dichloro derivative produced 1H‐pyrrolo[3,2‐c]‐pyridine (4).
Electrochemical reduction of cinoxacin. The unexpected formation of an isatin derivative
Authors: Dinner A. , Rickard E.
Published: April 2009

The electrochemical reduction of cinoxacin (I) has resulted, via a series of chemical and electrochemical steps, in the formation of an indole dione III.
Alkylation of picolinaldehyde with bromohydrins. A new class of heterocyclic ring tautomers
Authors: Dewhurst John Elton , Jones Paul R.
Published: April 2009

Entry into the pyrido[2, 1‐c] [1,4]oxazinium and pyrido(2,1‐c] [1,4]oxazepinium ring systems has been achieved by the interaction of picolinaldehyde with 2‐bromoethanol and 3‐bromo‐propanol, respectively. The products, ring‐tautomeric hemiacetals, are presumably formed by rapid hemiacetalization, followed by an intramolecular Menschutkin Reaction.
About the mechanism of formation of 3‐azidoindazole from 3‐diazoindazole or 3‐indazolyldiazo phenyl sulphide and potassium azide
Authors: Slanovnik B. , Tišler M. , Polanc S. , Janežič D.
Published: April 2009

It has been shown by mass spectrometrie analysis that 3‐azidoindazole, the product of the reaction between 3‐diazoindazole and azide ion, was formed through acyclic pentazene(IV and V) and cyclic pentazole (VIII and IX) intermediates in the ratio 2:1.
Studies on the syntheses of analgesics. Part 50. Synthesis of optically active 2‐[4‐(1‐oxo‐2‐isoindolinyl)phenyl]propanoic acid. [Studies on the syntheses of heterocyclic compounds. Part 742]
Authors: Kametani Tetsuji , Kigasawa Kazuo , Hiiragi Mineharu , Ishimaru Haruhide , Haga Seiji , Shirayama Keiko
Published: April 2009

2‐[4‐(1‐Oxo‐2‐isoindolinyl)phenyl]propanoic acid (1) having a potent analgesic and anti‐inflammatory activity could be obtained by three methods, which were found to provide extremely useful ways for the synthesis of 1 from the industrial point of view. (E)‐ and (Z)‐Isomers of 2‐butenoic acid and oxiranecarboxylic acid derivatives as the intermedaites in the synthesis of 1 were separated and characterized. Furthermore, the optical resolution of (±)‐2‐[4‐(1‐oxo‐2‐isoindolinyl)phenyl]propanoic acid was successfully achieved using cinchonidine as a resolution reagent.
Thiazoles and thiadiazines. The condensation of ethyl 4‐chloroacetoacetate with thiosemicarbazide
Authors: Campaigne E. , Selby T. P.
Published: April 2009

By varying the acidity, solvent polarity, and temperature when thiosemicarbazide reacted with ethyl 4‐chloroacetoacetate, ethyl 2‐amino‐6H‐1,3,4‐thiadiazine‐5‐acetate hydrochloride, ethyl 2‐hydrazinothiazole‐4‐acetate, and ethyl 2‐imino‐3‐aminothiazoline‐4‐acetate hydrochloride were prepared selectively. Double bond migration occurred after neutralizing the thiadiazine and thiazoline hydrochlorides to form the α,β‐unsaturated esters: 2‐amino‐5‐carbethoxymethylidene‐4,5‐dihydro‐6H‐1,3,4‐thiadiazine and 2‐imino‐3‐amino‐4‐carbethoxymethylidenethiazolidine. Pmr studies revealed that an equilibrium existed in solution between the imine and enamine tautomers of the thiadiazine free base. In the enamine structure, a 6‐membered hydrogen bonded ring system promotes stability. The thiadiazine contracted in acidic aqueous acetone to ethyl 2‐isopropylidenehydrazonothiazole‐4‐acetate.

Monobenzoylation at the primary amine of the thiadiazine yielded ethyl 2‐benzamido‐6H‐1,3,4‐thiadiazine‐5‐acetate without disruption of the hydrogen bonded ring, but benzoylating the imino functionality of the thiazolidine caused deconjugation of the α,β‐unsaturated ester by double bond migration back into the ring, and ethyl 2‐benzimido‐3‐aminothiazoline‐4‐acetate was produced, dehydration yielded ethyl 2‐phenylthiazolo[3,2‐b]‐s‐triazole‐5‐acetate. This compound was also obtained by reacting 3‐phenyl‐1,2,4‐triazole‐5‐thiol with ethyl 4‐chloroacetoacetate, while the monobenzoylated derivative of the hydrazinothiazole, ethyl 2‐(2‐benzoylhydrazino)thiazole‐4‐acetate underwent a dehydrative cyclization to ethyl 3‐phenyl‐thiazolo [2,3‐c]‐s‐triazole‐5‐acetate.

In chloroform solvent, the second site of benzoylation on the thiadiazine was ring nitrogen 3 while in ethanol or acetonitrile‐pyridine ring nitrogen 4 was benzoylated instead. Benzoylation at ring nitrogen 3 resulted in deconjugation of the α,β‐unsaturated ester moiety and formed the endocyclic imine, ethyl 2‐benzimido‐3‐benzoyl‐2,3‐dihydro‐6H‐1,3,4‐thiadiazine‐5‐acetate. However, deconjugation of the unsaturated ester did not occur after benzoylation at ring nitrogen 4; the product was trans‐2‐benzamido‐4‐benzoyl‐5‐carbethoxymethylidene‐4,5‐dihydro‐6H‐1,3,4‐thiadiazine.

The hydrogen bonded oximes, syn‐2‐amino‐5‐ethyloxalyl‐6H‐1,3,4‐thiadiazine oxime, 3,3‐dimethyl‐5‐ethyloxalyl‐2H‐1,2,4‐triazolo[3,4‐b]thiazole oxime, and 2‐(2‐benzoylhydrazino)‐4‐ethyloxalylthiazole oxime were synthesized by nitrosation.

2‐Amino‐5‐ethyloxalyl‐6H‐1,3,4‐thiadiazine oxime benzoate, 2‐benzamido‐5‐ethyloxalyl‐6H‐1,3,4‐thiadiazine oxime dibenzoate, and the tribenzoylated derivatives, 2‐benzimido‐3‐benzoyl‐5‐ethyloxalyl‐2,3‐dihydro‐6H‐1,3,4‐thiadiazine oxime benzoate and 2‐benzamido‐4‐benzoyl‐5‐ethyl‐oxalyl‐4H‐1,3,4‐thiadiazine oxime benzoate, of the thiadiazine oxime werè prepared. The oxime benzoylated first, the primary amine second, and the number 3 and 4 ring nitrogens last.
Some derivatives of 4H‐pyrano[4,3‐d]thiazole, a novel ring system
Authors: Philipp Adolf H. , Humber Leslie G. , Martel René R.
Published: April 2009

A synthesis of the novel 4H‐pyrano[4,3‐d]thiazole ring system is described. Derivatives bearing alkylamine and alkanoic acid side chains have been prepared and tested for potential antidepressant and antiinflammatory activities, respectively; only marginal activities were found in these tests.
The insertion and extrusion of heterosulfur bridges. VII. Desulfurization of phenanthro[4,5‐bcd]thiophene by means of methanol and a molybdena catalyst
Authors: Klemm L. H. , Karchesy Joseph J. , Lawrence Ross F.
Published: April 2009

Phenanthro[4,5‐bcd]thiophene (1) is converted into phenanthrene (2) (50%) and a mixture of methylphenanthrenes (3) (12%) by means of methanol and a sulfided cobaltous oxide‐molybdic oxide‐aluminum oxide catalyst (CMA‐1) at 450° in a flow system. Similarly, 2 gives 3; and 4‐methylphenanthrene yields 2 plus 3 (main component 3‐methylphenanthrene) under the same reaction conditions. Mechanisms of the reactions are discussed. A facile chromatographic separation for 1‐ and 4‐keto‐1,2,3,4‐tetrahydrophenanthrenes is presented.
The mass spectra of four‐membered alicyclic sulfur compounds
Authors: Scala A. A. , Colon Ismael
Published: April 2009

The mass spectra of thietane, trimethylene sulfoxide, and trimethylene sulfone are reported. The major competing reactions are four‐center fragmentation, heteroatom group elimination and rearrangement. The oxidation state of the sulfur atom has a profound effect upon the competition among these reaction channels. As the oxidation state of the sulfur increases the molecular ion becomes increasingly less stable and consequently the amount of rearrangement decreases. Elimination of the heteroatom increases as its oxidation state increases, while the amount of four‐center fragmentation decreases.
Linearly fused isoquinolines. Part II. The synthesis of the s‐triazolo[4,3‐b]isoquinoline system
Authors: Hajós Gy. , Messmer A.
Published: April 2009

3‐Hydrazinoisoquinoline (2) was synthesized via its N‐oxide derivative by removal of the N‐oxide funçtion with titanium trichloride. Acylation of the hydrazino compound (2) led to suitable starting materials (4 and 6) for cyclization to the novel, linearly fused ring system: tri‐azolo[4,3‐b]isoquinoline, which was more stable in the form of its perchlorate salt. The structure of the first representatives of the new ring system was proved by ir, nmr and ms spectroscopy.
Synthesis of 3‐formylbenzo[b]furan and 1‐methyl‐3,4‐dihydrobenzo[b]‐furo[2,3‐c]pyridine
Authors: Shafiee A. , Mohamadpour M.
Published: April 2009

Starting from the readily available 3‐methylcoumarilate, 3‐formylbenzo[b]furan was synthesized in high yield. The latter could be converted to 1‐methyl‐3,4‐dihydrobenzo[b]furo‐[2,3‐c]pyridine in moderate yield.
New routes to 1‐deoxy‐(3,4‐dihydro‐7,8‐dimethyl‐2,4‐dioxopyrimido[4,5‐b]‐quinolin‐10(2H)yl)‐D‐ribitols (5‐deazariboflavins)
Authors: Ashton Wallace T. , Brown Ronald D. , Tolman Richard L.
Published: April 2009

The acid‐catalyzed reaction of 6‐(N‐D‐ribityl‐3,4‐xylidino)uracil (1) with trimethyl ortho‐formate yields a bis(methoxymethylene) derivative (2), which is readily deprotected to give 5‐deazariboflavin (3). Correspondingly, 5‐methyl‐5‐deazariboflavin (6) is produced by cyclization of the tetraacetate of 1 with acetyl chloride in the presence of stannic chloride followed by deacetylation.
On the oxidation of N‐methylpyrimidinium salts
Authors: van der Plus H. C. , Buurman D. J.
Published: April 2009

Oxidation of 1,2‐dihydro‐1,3‐dimethyl‐2‐oxopyrimidinium bisulfate (1+·HSO) with hydrogen peroxide in acetic acid in the presence of potassium iodide gave 1,3‐dimethyl‐5‐iodouracil (65‐70%), 1,3‐dimethyluracil (10‐15%) and 3‐methyl‐2,4‐oxazolidinedione (10‐15%). Similar results were obtained on oxidation of the iodide (1+·I−). Oxidation of 1‐methyl‐4‐phenylpyrimidinium iodide or oxidation of 1‐methyl‐4‐phenylpyrimidinium methylsulfate in the presence of potassium iodide gave 1,6‐dihydro‐5‐iodo‐1‐methyl‐6‐oxo‐4‐phenylpyrimidine.
bis‐Isatoic anhydrides I. The preparation of bis‐isatoic anhydrides
Authors: Hall Randall W. , Bernhardt F. Christian , Beam Charles F.
Published: April 2009

bis‐Isatoic anhydrides have been prepared in 20‐40% yield by the treatment of sodio‐isatoic anhydride with alkane dibromides and ditosylates.
Selenium heterocycles XXIII. Synthesis of 4,5‐dihydrophenanthro[1,3‐d]‐1,2,3‐selenadiazoles and 10,11 ‐dihydrophenanthro[1,2‐d]‐1,2,3‐selenadiazoles
Authors: Lalezari I. , Sadeghi‐Milani S.
Published: April 2009

The selenium dioxide oxidation of a series of 1,2,3,4‐tetrahydrophenanthrone and 1,2,3,4‐tetrahydrophenanthren‐4‐one semicarbazones afforded 4,5‐dihydrophenanthro[4,3‐d]‐1,2,3‐selenadiazoles and 10,11‐dihydrophenanthro[1,2‐d]‐1,2,3‐selenadiazoles. The latter series which represent a new type of selenaazasteroidal compounds were pyrolyzed and gave the corresponding 1,4‐deselenine derivatives.
N,N‐Disubstituted 4‐amino‐3‐chloro‐5,6‐polymethylene‐2H‐pyran‐2‐ones
Authors: Evangelisti Filippo , Bignardi Gaetano , Bargagna Alberto , Schenone Pietro
Published: April 2009

The title compounds were obtained by dehydrochlorination with collidine, DBN or triethyl‐amine of N,N‐disubstituted 4‐amino‐3,3‐dichloro‐3,4‐dihydro‐5,6‐polymethylene‐2H‐pyran‐2‐ones already described.
A facile synthesis of 2‐phenylbenzo[b]thiophene‐3‐amine and the corresponding S‐oxides
Authors: Beck James R.
Published: April 2009

A rapid synthesis of 2‐phenylbenzo[b]thiophene‐3‐amine and its S‐oxides from o‐nitrobenzonitrile is described. Also reported is the preparation of 2‐phenylbenzo[b]thiophene‐3‐(2H)one, 1,1‐dioxide from methyl o‐nitrobenzoate.
Reaction of thiete 1,1‐dioxide with α‐chlorobenzalphenylhydrazine and methyl phenylhydrazonochloroacetate
Authors: Croce Piero Dalla , Del Buttero Paola , Mayorana Stefano , Vistocco Raffaele
Published: April 2009

Thiete 1,1‐dioxide reacts with 2 moles of α‐chlorobenzalphenylhydrazine and methyl phenylhydrazonochloroacetate in the presence of triethylamine leading to the pyrazole derivatives 6 and 7 whose structure and mechanism of formation are discussed.
New synthesis of condensed heterocycles from isoxazole derivatives VI. 2,5‐Dimethyl‐3‐aeetyl‐7‐amino‐1H‐pyrrolo[3,2‐b] pyridine
Authors: Aiello E. , Dattolo G. , Cirrincione G. , Plescia S. , Daidone G.
Published: April 2009

A new synthesis of pyrrolo[3,2‐b] pyridine starting with pyrrole ring is described. The procedure allows the synthesis of 4‐azaindoles bearing a sensitive group at C‐7. The nitration of 4b with nitric acid and acetic anhydride at −15° gave 5. The hydrogenation of 5 led to simultaneous reduction of N‐hydroxy and nitro groups and to hydrogenolysis of the isoxazole nucleus, affording an appropriate chain of atoms to building up the pyrrolo[3,2‐b] pyridine ring.
Mechanism study of base‐catalyzed cyclization of 2‐nitrophenylhydrazine in aqueous solution
Authors: Munson James W. , Hodgkins Thomas G.
Published: April 2009

The mechanism of cyelizalion of 2‐nitrophenylhydrazine to 1‐hydroxybenztriazole in alkaline aqueous solutions is studied. Kinetic parameters, product distribution and activation parameters are determined. A mechanism involving direct attack of the β‐hydrazino nitrogen on the nitrogen ol the nilro group with elimination of water is postulated. Substituted 2‐nitrophenylhydrazines are synthesized and studied under the same conditions.
Synthesis of 1,3‐dihydro‐2H‐benzimidazol‐2‐one from 2‐aminobenzamide
Authors: Heyman Duane A.
Published: April 2009

A method for the synthesis of 2‐henzimidazolone (1) has been devised which does not depend on 1,2‐diaminobenzene (2) as a starting material. This method produces 1 in good yield by the reaction of hypohalite with 2′‐carbamoylphthalanilic acid (7), a compound readily prepared by the reaction of 2‐aminobenzamide (3) and phthalic anhydride. Contrary to prior indications 1 can be hydrolyzed in the presence of acid at temperatures greater than 200 giving excellent yields of 2.
Synthèse de systèmes comportant deux cycles thiophéniques orthocondensés à un hétérocycle à sept chainons
Authors: Meunier P.
Published: April 2009

La réduction du carbonyle de dérivés des bithiényles porteurs sur chacun des cycles thiophéniques, d'un groupe formyle lié à l'atome de carbone voisin de la jonction intercyclique, conduit aux dialcools primaires attendus. Ces dialcools peuvent donner naissance aux bithiényles bis‐halogénomethylés correspondants. Par deshydratation des alcools et par action du sulfure de sodium ou d'amines sur les halogénures obtenus, on accéde respectivement à des dihydrodithieno[c,e]oxépinnes, thiépinnes et azépines. Lesdérivés tétraméthylés des “oxépinnes” précédentes ont été obtenus à partir de bithiényles diacé'tylés.
Synthesis of α‐hydroxy‐β‐lactams
Authors: Marthas M. S. , Amin S. G. , Chawk H. P. S. , Bose Ajay K.
Published: April 2009

A convenient synthesis of α‐hydroxy‐β‐lactams has been devised that involves the annelation of an inline with benzyloxyacetyl chloride and triethylamine and subsequent hydrogenolysis in the presence of palladium on carbon. In most cases a cis‐β‐lactam was obtained. A thioimidate can also be used as the imino component in the annelation reaction but the hydrogenolysis step fails. The annelation of the appropriate thiazoline to a 6‐epi‐penicillin derivative occurred much more readily with benzyloxyacetyl chloride than with azidoacetyl chloride.
New polycyclic pyran ring systems
Authors: Mazzei Mauro , Roma Giorgio , Ermili Aldo
Published: April 2009

Reaction of 1‐oxo‐3‐dialkylamino‐1H‐naphtho[2,1‐b]pyrans, 4‐hydroxycoumarin and formaldehyde gave rise to the formation of 1‐oxo‐2‐((2‐oxo‐4′‐hydroxy‐2′H‐1′‐benzopyran‐3′‐yl)‐melhyl J‐3‐dialkylamino‐1H‐naphtho[2,1‐b]pyrans. When these compounds were refluxed in glacial acetic acid, cyclization occurred and 6,8‐dioxo‐6H,7H,07‐,5,15,16‐trioxadibenzo[a,j]‐naphthacene arose by cleavage of the dialkylamino group. In a similar manner, starting from suitable products, many other trioxanaphthacene or azadioxanaphthacene derivatives were synthesized.
Magnetic circular dichroism spectra of some 3‐arylfervenulins and 3‐aryltoxoflavins
Authors: Yamaguchi H. , Kuwata R. , Yoneda F.
Published: April 2009

The magnetic circular dichroism (MCU) spectra of some 3‐arylfervenulins and 3‐aryltoxo‐flavins were measured. From the dependence of the Faraday B values of 3‐arylfervenulins and 3‐aryltoxoflavins on the Hammet σpara values, it is concluded that the substituent effects on the Faraday B values of 3‐aryltoxoflavins are reverse to the substituent effects on the Faraday B values of 3‐arylfervenulins and the reverse property of 3‐aryltoxoflavins concerning the substituent effects rises from the contribution of the 1,5‐dipolar structure of 3‐aryltoxoflavins.
Photochimie d'hétérocycles azotés. IV. Transposition de type photo‐fries des N‐acétyl benzimidazolones
Authors: Bouchet Philippe , Joncheray Gerard , Jacquier Robert , Elguero José
Published: April 2009

La photolyse des N‐acé'tyl et N,N ‐diacétyl benzimidazolones en solution dans le benzéne ou l'alcool 95 conduit à des mélanges de produits de désacétylation, d'ortho‐transposition et de para‐transposition. Les différents produits obtenus ont été identifiés par rmn, spectrométrie de masse et synthése univoque.
Über die acetolysenprodukte der cyanhydrine von 4‐pyridazoin und 4‐pyridoin: Struktur und ungewöhnliche reaktivität 9. Mitteilung über pyridazine
Authors: Heinisch Gottfried , Luszczak Ernst , Mayrhofer Andreas
Published: April 2009

4‐Pyridazoin‐eyanhydrin liefert mit Aeetanhydrid das 1,4‐Dihydropyridazin‐Derivat 2a. Die Strukturen von 2a und dem Pyridin‐Analogon 2b werden spektroskopisch gesichert. Bei Chromatographie auf Kieselgel, gefolgt von Elution mit Methanol reagiert 2a zum Pyridazin‐4‐carbonsäuremethylester, 2b liefert hingegen neben Isonicotinsäuremethylester 4‐Pyridymethyl acetat. Die Mechanismen dieser ungewöhnlichen Reaktionen werden diskutiert.
Reactivity of 4‐hydroxy‐2‐methyl‐7,8,9,10‐tetrahydrobenzo[h] quinoline towards base‐catalyzed cyclization, mannich and turpin reactions
Authors: Abbasi M. , Nasr M. , Zoorob H. H. , Michael J. M.
Published: April 2009

Mannich reaction upon 4‐hydroxy‐2‐methyl‐7,8,9,10‐tetrahydrobenzo[h]quinoline (1) as well as its nitration were studied. Condensation of the chloroquinoline 6b with sodium azide, benzylamine and ethanolamine gave the quinoline derivatives 6c, 6f and 6g, respectively. Phenylhydrazine and sodium borohydride effected reduction of the azidoquinoline 6c to the corresponding amino‐ and hydroxyamino derivatives 6d and 6e, respectively. Also, Turpin's reaction gave the benzoquinobenzoxazines 7a‐d when applied to 6b. Treatment of 6f, 6g with alkali and the condensation of 6b with glycine in alcoholic sodium carbonate solution afforded the imidazo[4,5‐c]quinoline derivatives 9a‐c, respectively.
A side reaction encountered in using the peptide coupling reagent N‐ethoxycarbonyl‐2‐ethoxy‐1,2‐dihydroquinoline (EEDQ)
Authors: Lombardino Joseph G. , Anderson Susan L. , Norris Charles P.
Published: April 2009

An unusual side reaction has been found during an attempt to form an amide link between 2‐aminothiazole and thiophene‐2‐carboxylic acid in the presence of EEDQ. Ethyl N‐(‐thiazolyl)‐carbamate (3) was isolated in significant amounts indicating that 2‐aminothiazole, and perhaps other heterocyclic amines, can react directly with EEDQ to form carbamates.
Organolithium addition to 5,6‐disubstituted pyrimidines
Authors: Bennett Gregory B.
Published: April 2009

The addition of organolithium reagents to the azomethine bond of 5,6‐disubstituted pyrimidines provided, in every case, a single adduct. When reacted with either ethyl chloro‐formate or hydrogen chloride, these adducts gave a single dihydro pyrimidine. The resulting N‐H dihydro pyrimidines were oxidized with potassium permanganate to the corresponding pyrimidines.
Synthesis of some 3‐aryl‐4‐oxothiazolin‐2‐yl‐[3‐(2‐aryl)indolyl]hydrazories
Authors: Agrawal A. K. , Hastogi V. K. , Parmar S. S.
Published: April 2009

Several 4‐aryl‐l‐[3‐(2‐aryl)indolyl]‐3‐thiosemiearbazones and 3‐aryl‐4‐oxothiazolin‐2‐yl‐[3‐(2‐aryl)indolyl] hydrazones were synthesized as possible antilertility agents. J. Heterocyclic Chem., 15, 677 (1978)
Synthesis of l‐(N‐acelylpiperidino)‐4‐aryl semicarbazides as possible anticonvulsants
Authors: Misra R. S. , Dwivedi C. , Parmar S. S. , Singh S. P.
Published: April 2009

Six 1‐(N‐acetylpiperidino)‐4‐aryl semicarbazides were synthesized from ethyl‐N‐piperidino‐aeetatc which on treatment with hydrazine hydrate was converted into N‐piperidinoacethydrazide. The resulting hydrazide on treatment with the appropriate arylisoeyanales formed l ‐(N‐acelyl‐piperidino)‐4‐aryl semicarbazides. Amongst these piperidinosemicarbazides, three compound possessed low anticonvulsanl activity and provided 20‐40% protection against pentylenetetrazol‐induced convulsions in mice. All piperidino semicarbazides (0.1 mM) possessed antihemolytic activity (13‐35%) and caused 40‐72% inhibition of monoamine oxidase activity of rat brain homogenates at a final concentration of 0.3 mM.
An oxidation with thionyl chloride
Authors: Walser Armin , Flynn Thomas
Published: April 2009

The reaction of the 2‐methylquinoline‐3‐carboxylic acid 1b with thionyl chloride gave the dichlorothiolactone 2, the structure of which was confirmed by chemical transformations.
2,3,9,10‐Tetrachlorobenzo[1,2‐b: 4,5‐b']bis[1,4]benzodioxin, a homologue of TCDD
Authors: Oliver James E. , Lusby William R.
Published: April 2009

Catechol and 4,5‐dichlorocatechol have been condensed with 1,5‐dichloro‐2,4‐dinitrobenzene to provide benzo[1,2‐b: 4,5‐b ]bis[1,4]benzodioxin and its 2,3,9,10‐tetrachloro derivative, respectively. The latter compound is a novel homologue of the extremely toxic 2,3,7,8‐tetrachloro‐dibenzo‐p‐dioxin (TCDD).
Systèmes aromatiques à 10 électrons π dérivés de l'aza‐3a pentalène. XXXII. Recherches dans la série du pyrazolo[1,5‐a]benzimidazole
Authors: Lazaro René , Elguero José
Published: April 2009

Le probleme de l'aromatiuité d'un dérivé aza‐3a pentalénique, le méthyl‐2 pyrazolo[1,5‐a]‐benzimidazole, a été abordé par 1′étude de sa réactivité comparée à celle d'un produit modèle, le phényl‐1 méthyl‐3 amino‐5 pyrazole. La mono‐ et diprotonation, l'alcoylation, la quater‐narisation, la formylation, l'acétylation et le comportement des dérivés N‐acétylés ont été examinés. On eonclue à une structure aromatique fortement polarisée.
On the synthesis and animation of 5‐chloro‐and 5‐bromo‐1,7‐naphthyridine
Authors: Woźaniak M. , van der Plas H. C.
Published: April 2009

A new synthesis of 5‐chloro‐ and 5‐bromo‐1,7‐naphthyridine, using 8‐amino‐1,7‐naphthyridine as starting material is described. On amination with potassium amide in liquid ammonia, the 5‐bromo compound undergoes a tele‐amination into 8‐amino‐ and 2‐amino‐1,7‐naphthyridine and a Chichibabin reaction yielding 8‐amino‐5‐bromo‐1,7‐naphthyridine. The reaction with the 5‐chloro compound occurs at a much lower rate than the 5‐bromo compound and only gives 8‐amino‐5‐chloro‐1,7‐naphthyridine in a small yield. Convincing 1H‐nmr evidence is presented, showing that the 5‐bromo‐ and 5‐chloro‐1,7‐naphthyridine give addition of the amide ion at position 8 and that the 5‐chloro compound also gives addition at position 2.
The knoevenagel condensation of ethyl acylpyruvates
Authors: Kurihara Takushi , Sakamoto Yasuhiko , Kobayashi Toshio , Mori Masanobu
Published: April 2009

Extensive studies of the Knoevenagel condensation of aromatic aldehydes and active methyl‐lene compounds have been reported (2). In 1894, Knoevenagel reported (3) the reaction of benz‐aldehyde with ethyl benzoylpyruvate in the presence of piperidine to give ehtyl benzyl‐(bis‐benzoyl)pyruvate, m.p. 162°, but no yield of the product was reported. This paper deals with the interesting results of the reactions of ethyl acetylpyruvate (2) (4) and ethyl benzoylpyruvate (3) (5) with some aromatic aldehydes (1a‐f).
Zur darstellung der l‐(diazinyl)‐2‐(pyridyl)‐äthene (triazastilbene)
Authors: Felbecker H. , Hollenberg D. , Schaaf R. , Bluhm Th. , Perkampus H.‐H.
Published: April 2009

In Weiterführung unserer Untersuchungen an Azaanalogen des Stilbens warden die 18 isomeren l‐(Diazinyl)‐2‐(pyridyl)‐äthene (Triazastilbene) dargestellt. Zur Diskussion der Aktivierung der Methylgruppen und der Carbonylgruppen bei den Edukten für die Aldolkondensation wurden die Ergebnisse von Elektronendichteberechnungen nach der CNDO/2‐Methode herangezogen.
Carbon‐13 spectra of some tetrahydropyridines. The structure of the tetrahydropyridines from 3,5‐lutidine 1‐oxide and mercaptans in acetic anhydride
Authors: Kokosa John M. , Chu Ih , Bauer Ludwig , Hlgan Richard S.
Published: April 2009

The reaction of 3,5‐lutidine 1‐oxide (1) with t‐butyl mereaptan in acetic anhydride, with or without triethylamine, was reinvestigated. There was obtained 2‐t‐butylthio‐3,.5‐lutidine as the major product, a small quantity of 3‐(t‐bulylthio)methyl‐5‐picoline, 1‐acetyl‐2,3‐diacetoxy‐3,5‐dirnethyl‐6‐t‐butylthio‐1,2,3,6‐tetrahydropyridine (which represents a structure revision) and l‐acetyl‐2,6‐dihydroxy‐3‐t‐butylthio‐3,5‐dimethyl‐1,2,3,6‐tetrahydropyridine. A similar reaction of 1 with 1‐adamantyl mercaptan furnished 2‐(l‐adamantylthio)‐3,5‐lutidine and 1‐acetyl‐2,3‐diacetoxy‐3,5‐dimethyl‐6‐(1‐adamantylthio)‐1,2,3,6‐tetrahydropyridine. The structures of these new tetrahydropyridines were established primarily by carbon‐13 nmr spectra.
Etude de nouveaux systemes aromatiques possédant des propriétes diéniques: [2]benzothiéno[5,6‐g] phtalazines, thiéno[3,4‐g]phtalazines et leurs analogues furanniques
Authors: Lepage Lucette , Lepage Yves
Published: April 2009

De nouveaux systémes polydiéniques sont déerits: deux [2]benzothiéno[ 5,6‐g]phtalazines, analogues diazotés des anthra[2,3‐c] thiophénes ineonnus, une f'uro[3,4‐g]phtalazine et une thiéno[3,4‐g]phtalazine. Ces différents composés subissent la réaction de Diels et Alder. Des tetraza‐2,3,8,9 naphtacénes ont été synthetise's pour la première fois. Les structures de ces composés ont été démontrées par des méthodes chimiques et spectrographiques.
Synthesis and nuclear magnetic resonance spectra of 2H‐pyrido [1,2‐a] pyrimidin‐2‐ones
Authors: Al‐Jallo Hikmat N. , At‐Biaty Ibtisam A.
Published: April 2009

Reaction of ethyl phenylpropiolate with several 2‐aminopyridines afforded the corresponding 2H‐pyrido[1,2‐a] pyrimidin‐2‐ones in good yields. Analysis of the nmr spectra of these compounds and their hydrobromides were based on comparing their spectra with their 3‐deuterated analogues. It was found that in these 2‐oxo compounds, the proton at position‐7 is shielded and absorbs together with the olefinie proton at position‐3 in the region of 5 6.35‐6.70 ppm. The latter proton could be used for differentiating these compounds from the corresponding 4‐oxo isomers which have already been identified by the deshielded proton at pusition‐6 near § 9.0 ppm. The ir and nmr spectral data for all these compounds are tabulated and discussed.
Ring‐chain tautomerism of aldehyde n‐methylated semicarbazones
Authors: Uda Masayuki , Kubota Seiju
Published: April 2009

Ring‐chain tautomerism of thirty‐six aldehyde semicarbazones was studied by nmr spectro‐scopy. The 2,4‐dimethylsemicarbazones of benzaldehyde,p‐tolualdehyde,p‐anisaldehyde, andP‐chlorobenzaldehyde exist as chain forms in DMSO‐d6, but as both ring and chain forms in deuteriotriiluoroacetic acid. Unlike these semicarbazones, the aldehyde semicarbazones ofN‐unsubstituted semicarbazide, 2‐methylsemicarbazide, and 4‐methylsemicarbazide did not cyclo‐isomerize in either DMSO‐d6or deuteriotrifluoroacetic acid. These results indicate that protona‐tion of the C=N nitrogen atom and steric hindrance of the 2‐methyl group with an aromatic group at the C=N carbon atom in the chain form cause cycloisomerization to ring isomers.
Sels d'aziridinium stables, C‐fonctionnalisés
Authors: Pierre Jean‐Louis , Baret Paul , Rivoirard Eve‐Marie
Published: April 2009

La réaction de diverses aziridines C‐fonctionnalisées avec le fluorosulfonate de méthyle conduit avec des rendements élevés aux fluorosulfonates d'aziridinium correspondants. Ces composés sont caractérisés sans ambiguïté par voie chimique. La réaction d'ouverture des sels d'aziridinium par le chlorure de lithium est étudiée. Deux méthodes quantitatives de changement du contre‐ion sont décrites.
Synthesis and nuclear magnetic resonance spectra of fused pyrimidines
Authors: Al‐Jallo Hikmat N. , Muniem Muhamad A.
Published: April 2009

Ethy phenylpropiolate reacted with 2‐aminobenzothiazoles, benzimidazoles, thiazoline and thiazole to give the corresponding fused 2‐oxopyrimidines. 2‐Mercaptobenzimidazole reacted with ethyl phenylpropiolate to give 4‐phenyl‐2H‐1‐thiapyrimido(1,2‐a ]benzimidazol‐2‐one in very good yield. The thiones, methylthio iodides and the hydrobromides of some of the products were prepared. Analysis of the nmr spectra of the benzothiazole and benzimidazole products and their 3‐deuterio analogs showed that the proton at position 6 is shielded and absorbs together with the proton at position 3 near δ 6.0 ppm. The nmr and ir spectral data of all the products are tabulated and discussed.
Synthèse de dérivés O‐substitués du (dihydroxy‐3′,4′ phényl)‐2 indole par utilisation de groupes protecteurs sulfonylés
Authors: Bazile Yves , De Cointet Paul , Pigerol Charles
Published: April 2009

On synthétise les dérivés O‐substitués du (dihydroxy‐3′,4′ phényl)‐2 indole au départ d'acétovanillone par différentes méthodes qui mettent en évidence l'intérět du groupe protecteur benzènesulfonyle et méthylsulfonyle. En effet la protection de l'hydroxyle de l'acétovanillone par de tels groupements facilite la cyclisation de Fischer et, plus particulièrement, celle de Bischler. De plus, elle autorise les réactions de O‐déméthylation et de O‐alkylation sélectives. Enfin elle permet de régénérer aisément le groupe hydroxy greffé en position ‐4′ sur les (alkyloxy‐3′ phényl)‐2 indoles.
Synthesis of substituted 2‐ethyl‐3‐(4‐hydrazinocarbonylphenyl)‐4‐quinazo‐lones and 2‐ethyl‐3‐(4‐hydrazinocarbonylmethylphenyl)‐4‐quinazolones
Authors: Arora R. C. , Rastogi V. K. , Agrawal A. K. , Parmar S. S.
Published: April 2009

Some substituted 2‐ethyl‐3‐(4‐hydrazinocarbonylphenyl)‐4‐quinazolones and 2‐ethyl‐3‐(4‐hydrazinocarbonylmethylphenyl)‐4‐quinazolones were synthesized and characterized by their sharp melting points, elemental analyses and spectral data.
Preparation of some tricyclic fused ring iminopyrido[3,2‐e]pyrimidines
Authors: Kwok Russell
Published: April 2009

The preparation of a number of tricyclic fused ring iminopyrido[3,2‐e]pyrimidines is described. Treatment of 2‐chloronicotinonitrile with primary amines afforded the corresponding 2‐amino derivative which was condensed with ethylenediamine or higher congeners to give substituted cyclic amidines. The latter on treatment with cyanogen bromide gave the desired imino‐pyrido[3,2‐e]pyrimidines. The preparation of diaminopyrido[2,3‐d]pyrimidines and tricyclic quinazolines by related procedures is discussed.
1H Nmr structural analysis of azabicyclospirohydantoins
Authors: Trigo G. G. , Galvez E. , Avendaño C.
Published: April 2009

Based on the data from 1H nmr spectra, the structure and spatial configuration of the ahove mentioned hydantoins are established. In the 3‐alkyl‐3‐azabicyelo[3.3.f ]nonane‐9‐spiro‐5′‐hydantoins analyzed, we confirm the chair‐chair configuration and the presence of only one stereoisomer at the spiro carbon atom (with the C4′=() group axial with regard to the piperidine ring). In the 3,7‐dialkyl‐3,7‐diazabieyclo[3.3.1 ]nonane‐9‐spiro‐5′‐hydantoins analyzed, we also confirm the chair‐chair configuration and we calculate the percentage of the two stereoisomers when they exist.
Tricyclic heteroaromatic ring systems II A convenient synthesis of 1H‐pyrrolo[3,2‐c]quinolines
Authors: Khan Misbahul Ain , da Rocha João Ferreira
Published: April 2009

Various quinol‐4‐yl hydrazones on heating in high boiling solvents undergo cyclizations to give lH‐pyrrolo[3,2‐c]quinolines in good yields. Some of these pyrroloquinolines were alkylated to provide their N‐alkyl derivatives.
Indole and quinoline derivatives of 2,3‐dihydro‐l‐benzothiepin‐4(5H) one
Authors: Pellicciari Roberto , Natalini Benedetto , Ricci A. , Alunni‐Bistocchi G. , De Meo G.
Published: April 2009

By application of the Friedlander synthesis on 2,3‐dihydro‐l‐benzothiepin‐4(5H) one (4), the corresponding [4,5‐b]quinoline derivatives 5a and 5b were obtained. Starting from the ketone (4) and by application of the Fischer indole synthesis, 1‐benzolhiepino[4,5‐b ]indole (6) and 1‐benzothiepino[4,5‐b]benzo[g]indole (7) were obtained. When β‐naphthylhydrazine was used in the indolisation reaction, a mixture of 1‐benzothiepino[4,5‐b]benzo[e]indole (8) and 1‐benzothiepino[4,3‐b]benzo[e] indole (9) was obtained.
An infrared spectroscopic investigation on N‐methyl‐1,3‐thiazolidine‐2‐thione and ‐2‐selone
Authors: Devillanova Francesco A. , Verani Gaetano , Sathyanarayana D. N.
Published: April 2009

An infrared investigation cm N‐methyl‐1,3‐thiazolidine‐2‐thione and ‐2‐selone in the range 4000‐200 cm−1 is reported. The v CS and v CSe vibrations give contributions to the absorptions around 1000 cm−1 and below 600 cm−1. The assignments are supported by comparison of their ir spectra with those of S‐ and Se‐methiodides. The π‐bond orders of the thio‐ and seleno‐ketonic links in these compounds are higher than those found for 1,3‐imidazolidine‐2‐thione and ‐2‐selone.
Synthesis and thermal reaction of 2‐perfluoropropyl or (2‐pyridyl)‐5‐phenyl‐6‐[4‐(4‐ethynylphenoxy) phenyl] ‐as‐triazine
Authors: Hergenrother P. M. , Sykes G. F. , Young P. R.
Published: April 2009

4‐(4‐Ethynylphenoxy) benzil was separately reacted with two amidrazones to provide acetylene‐containing phenyl‐as‐triazine products. Each product consisted of two isomers which were separated by high pressure liquid chromatography and analyzed by mass spectroscopy. Differential scanning calorimetry was employed to study the thermal reaction of the acetylene‐containing phenyl‐as‐triazine products. The principal component from the thermally induced reaction of the acetylene‐containing phenyl‐as‐triazine was identified by mass spectroscopy as a dimer.
Analogues of antipsychotic phenothiazines. 10‐(β‐dialkylamino) ethylaminophenothiazines
Authors: Corral Carlos , Lissavetzky Jaime , Quintanilla Gloria
Published: April 2009

A series of 10‐(β‐dialkylaniino) ethylarninophenothiazines III was obtained by lithium alumi‐um hydride reduction of 10‐dialkylaminoacetylaminophenothiazines II. Compounds II were synthesized by intramolecular cyclization, via a Smiles rearrangement, of 2‐nitro‐2′‐(β‐dialkyl‐aminoacetyl) hydrazinodiphenyl sulfides I and XI, which in turn were best prepared by condensation of the appropriate dialkylaminoacetic acid hydrochloride with the corresponding 2‐nitro‐2′‐hydrazinodiphenyl sulfide in the presence of dicyclohexyl carbodiimide. Other attempted methods for the synthesis of compounds 1 are also described.
Polymethyl derivatives of furo[3,4‐c]pyran4‐one, furo[3,4‐c] pyridin‐4‐one and pyrrolo[3,4‐c]pyran‐4‐one
Authors: Giardina Dario , Ballini Roberto , Ferappi Marcello , Casini Giovanni
Published: April 2009

The: title compounds were prepared from Michael adducts, obtained from acetoacetic esters and trans‐3‐hexene‐2,5‐dione, and from the corresponding dehydration products, by direct cyclization to oxygen rings or by reaction with ammonia (or methylamine) to give nitrogen rings.