Reaction of heterocyclic diazonium salts with hydrazones

Depending on the nature of the heteroring and the hydrazone, a formazan or a heterylazophenylhydrazone are formed in the reaction of an aryl hydrazone with the diazonium salt obtained from a heterocyclic amine. Disproportionate to form a triphenylformazan is also possible.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1062–1064, August, 1972     

Reactions of quinazolinium salts with quaternary heterocyclic salts yielding 3-hetarylquinolines

A novel type of transformations of the pyrimidine ring under the action of C-nucleophiles was found and a new method was developed for the synthesis of 3-hetarylquinolines from quinazoline derivatives and quaternary heterocyclic salts. An independent synthesis was carried out and transformations of one of the probable intermediates were studied. By-products were isolated. The effects of the nature of the heterocycle and substituents on the course of the ring transformation reaction were found, and the mechanism of the reaction was suggested. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1210–1215, June, 1998.     

Reactions of heterocyclic cations with N-containing nucleophiles. 17. Synthesis of pyrylium salts with three-ring azole substituents

2,6-Diphenylpyrylium perchlorate was hetarylated with imidazo- and pyrrolo-[1,2-a]benzimidazoles, and deeply colored 4-azolylpyrylium perchlorates were obtained.See [1] for communication 16.Communication 24 from the series Research on imidazo[1,2-a]benzimidazole derivatives. See [2] for communication 23.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 309–313, March, 1987.     

Reactions of heterocyclic cations with nitrogen-containing nucleophiles. 12. Reaction of pyrylium salts with azomethines

The reaction of pyrylium salts with azomethines leads to the formation of styrylpyrylium, styrylpyridinium, and 4-arylbenzylaminopyrylium salts. The reaction of the latter with ammonia and amines gave pyridines and pyridinium salts with a tertiary amino group as a substituent.See [1] for Communication 11.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 465–468, April, 1982.     

Reactions with heterocyclic amidines VIII. Synthesis of some new imidazo[1,2-b]pyrazole derivatives

The reaction of benzoylacetonitrile (III) , its phenylazo derivative (X) , malononitrile and malononitrile derivatives with ethyl hydrazinoacetate was investigated. All the investigated compounds with the exception of phenylazobenzoylacetonitrile and phenylazomalononitrile afforded 1-ethoxycarbonylmethyl-3-aminopyrazole derivatives when treated with I. Compounds Xa and XVIII afforded imidazoypyrazole derivatives under the same experimental conditions.     

Reaction of 5-alkylidenerhodanines with diazonium salts

In the action of diazonium salts on 5-alkylidenerhodanines, azo compounds are formed by the replacement of one or two hydrogen atoms in the methyl group. In the case of 5-ethylidenerhodanines, the formation of an azorhodanine through the replacement of the alkylidene residue by an arylazo group takes place simultaneously. In the formazyl derivatives the long-wave absorption maximum is displaced hypsochromically by 15–20 nm as compared with the dyes having a single azo group.     

Activated nitriles in heterocyclic synthesis: Synthesis of several new coumarin derivatives

Several new benzopyran and benzopyranopyridine derivatives were synthesized via condensation of 2-amino-1,1,3-tricyanopropene (1) and diethyl 2-amino-1-cyanopropene-1,3-dicarboxylate (2) with salicylaldehyde and treatment of the resulted products with active methylene regents. The spectroscopic data of the synthesized compounds are reported and discussed.

---

Aktivierte Nitrile in der Heterocyclen-Synthese: Darstellung einiger neuer Cumarinderivate

Zusammenfassung Einige neue Benzopyran- und Benzopyranopyridin-derivate wurden durch Kondensation von 2-Amino-1,1,3-tricyanopropen (1) und 2-Amino-1-cyanopropen-1,3-dicarbonsäuredimethylester (2) mit Salicylaldehyd und Behandlung der Reaktionsprodukte mit aktiven Methylenreagenzien dargestellt. Die spektroskopischen Daten der neuen Verbindungen werden diskutiert.

     

Reactions of cyclic enaminoketones with benzylidenemalononitriles. Synthesis of new fused heterocyclic systems containing the 1,4-dihydropyridine fragment

The reactions of cyclic enaminoketones with benzylidenemalononitriles were examined and a new procedure was developed for the synthesis of fused heterocyclic systems containing the 1,4-dihydropyridine ring, viz., thienopyrimidoquinolines and furopyrimidoquinolines. The characteristic features of the reactions and the structures of the resulting compounds were investigated.     

Synthesis of salts of heterocyclic N- and C-nitramino-N-nitroimides

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, p. 1239, May, 1991.     

Reaction of some organomercury compounds with diazonium salts

Summary We were the first to replace a mercury atom attached to a saturated carbon atom by the arylazo group. The reaction of the p-nitro- and 2,4-dinitrophenyldiazonium fluoborates with ethyl -bromomercuriphenylacetate and with bromomercurimethyl tert-butyl ketone give the corresponding arylhydrazones in good yields.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1711–1712, September, 1964     

Reaction of heterocyclic betaines. Synthesis of a new heterocyclic system

A new condensed heterocyclic system, viz., 1,3,7,9-tetra-oxo-2,8-diphenyl-6-formylpyrimido [3,4-a]pyrimido[4,5-dloxazine, was synthesized, and its electronic and PMR spectra were recorded. Factors that affect the orientation of nucleophilic substitution in betaines of the pyrimidine series with aliphatic amines are discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 993–995, July, 1980.     

Reactions with heterocyclic diazonium salts: New routes for the synthesis of pyrazolo[1,5-c]-1,2,4-triazoles and pyrazolo[1,5-c]-as-triazines

3-Phenylpyrazole-5-(liazonium chloride ( 1 ) couples with α-chloro derivatives of acetylacetone, ethyl acetoacetate and aceto-o-anisidine to yield the corresponding pyrazole-5-yl hydrazonyl chloride derivatives 2a-c . Compounds 2a,b were cyclised to yield either the pyrazolo[1,5-c]-1,2,4-triazole derivatives 3a,b or the pyrazolo[1,5-c]-as-triazines 4a,b depending on the applied reaction conditions. Compound 2c cyclised only into 3c under different cyclization conditions. The pyrazolo[1,5-c]-as-triazine derivatives 4c-e could be prepared via condensation of 2a with potassium cyanide. Compound 2d reacted with aromatic thioles and with sodium benzene-sulphonate to yield the pyrazolo[1,5-c]-as-triazine derivatives 6a-d . Compound 1 reacted with activated double bond systems to yield pyrazolo[1,5-c]-as-triazines 8a,b and 9 .     

Synthesis and structure of some diazonium salts of the 1,2,4-triazole series

Diazotriazolecarboxylic acid, its methyl ester, and 3-diazonium-5-nitrophenyltriazoles have an internal salt structure. 3-Diazonium-5-methyl- and -5-phenyl-1,2,4-triazoles have been isolated as nitrates, perchlorates, and fluoroborates. All the compounds mentioned exist in strongly acid media as salts of the corresponding acid with diazo cations, but in weakly acid and neutral solutions they exist as zwitterions, formed by elimination of a proton from the imino nitrogen of the heterocycle.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 705–709, May, 1970.