Reaction of 4-oxoalkane-1,1,2,2-tetracarbonitriles with 1,3,5-trlaryl-2,4-diaza-1,4-pentadienes

2-Aryl-1,2,3,4-tetrahydropyridine-3,3,4,4,-tetracarbonitriles and 1,3,5-triaryl-9-oxo-1,2,3,4b,5,6,8a,9-octahydropyrido[3,4:3,4]pyrrolo[1,2-a][1,3,5]triazine-4b,8a-dicarbonitriles are formed by the reaction of 4-oxoalkane-1,1,2,2-tetracarnonitriles with 1,3,5-triaryl-2,4-diaza-1,4-pentadienes depending on the solvent used.Chuvash State University, Cheboksary 428015. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1395–1409, October, 1996. Original article submitted October 2, 1996.     

Reaction of 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles with hydrochloric acid

Russian Journal of Organic Chemistry -     

Decyanation of 5-Alkyl-6-aryl-4-oxocyclohexane-1,1,2,2-tetracarbonitriles

Russian Journal of Organic Chemistry -     

Synthesis of 5-amino-3H-pyrrole-3,4-dicarbonitriles from 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles

Russian Journal of Organic Chemistry -     

Reaction between 4-oxoalkane-1,1,2,2-tetracarbonitriles and morpholine: regioselective synthesis of 5-amino-2-(morpholin-4-yl)-3-(2-oxoalkyl)-3H-pyrrol-3,4-dicarbonitriles

A new approach to the regioselective synthesis of polyfunctional 3H-pyrroles from 4-oxoalkane-1,1,2,2-tetracarbonitriles is described. 5-Amino-3-(2-aryl-2-oxoethyl)-3H-pyrrol-3,4-dicarbonitriles are prepared from 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles. Diastereomeric 5-amino-2-morpholin-4-yl-3-(2-oxocyclohexyl)-3H-pyrrole-3,4-dicarbonitriles were obtained from 1-(2-oxocyclohexyl)ethane-1,1,2,2-tetracarbonitriles.     

Synthesis of a new organic anion by reaction of 4-aryl(hetaryl)-4-oxobutane-1,1,2,2-tetracarbonitriles with ammonia

Russian Journal of Organic Chemistry -     

A New Branch of the Diversity-Oriented Synthesis Based on 4-Oxoalkane-1,1,2,2-tetracarbonitriles: Synthesis of Cyano-Substituted Iminofuran Derivatives

4-Oxo-3,4-diphenylbutane-1,1,2,2-tetracarbonitrile reacted with aliphatic, aromatic, and heterocyclic aldehydes in the presence of ammonium acetate to afford previously unknown iminofuran derivatives, 5-imino-4-(2-oxo-1,2-diphenylethyl)tetrahydrofuran-3,3,4-tricarbonitriles.     

Reaction of 4-Oxocyclohexane-1,1,2,2-tetracarbonitriles and 5-Hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles with Amines

New methods have been developed for the synthesis of fused amino-substituted pyrrolidinones and dihydropyrrolones. 4-Oxocyclohexane-1,1,2,2-tetracarbonitriles react with ammonia, hydrazine, and hydroxylamine to give, respectively, 5-amino-, 5-hydrazino-, and 5-hydroxylamino-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles, while with phenylhydrazine, semicarbazide, and thiosemicarbazide, 6-hydrazono-, 6-semicarbazono-, and 6-thiosemicarbazono-3-amino-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-isoindole-3a,7a-dicarbonitriles are formed. The latter can also be obtained under analogous conditions from 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles. Reactions of 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles with diethylamine or triethylamine give 3-amino-1,6-dioxo-3a,4,5,6,7,7a-hexahydro-1H-isoindole-3a,7a-dicarbonitriles.     

Different Directions of the Reaction of 1-(2-Oxocycloalkyl)-ethane-1,1,2,2-tetracarbonitriles with Aqueous Ammonia

Russian Journal of Organic Chemistry - Tetracyanoethylene adducts of cycloalkanones, 1-(2-oxocycloalkyl)ethane-1,1,2,2-tetracarbonitriles, reacted with aqueous ammonia at room temperature to give,...     

Reactions of 6,6-dialkyl-5,7-dioxo-4,8-dioxaspiro[2.5]octane-1,1,2,2-tetracarbonitriles with O-centered nucleophiles

The reactions of 6,6-dialkyl-5,7-dioxo-4,8-dioxaspiro[2.5]octane-1,1,2,2-tetracarbonitriles with primary aliphatic alcohols lead to the formation of alkyl 2,2,3,3-tetracyanocyclopropanecarboxylates; the reactions of the same compounds with ketone oximes give 2-amino-4,4-bis(alkylideneaminooxy)-6-(alkylidene-aminooxycarbonyl)-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitriles, while with aldehyde oximes 2-amino-2-oxo-1,5-dicyano-3-azabicyclo[3.1.0]hex-2-ene-6-carboxylic acid is formed.     

Spiro heterocyclization of 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles to 3H-pyrrole derivatives, 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes

4-Aryl-3-methyl-4-oxobutane-1,1,2,2-tetracarbonitriles reacted with morpholine to give 8-amino-3-aryl-1-imino-4-methyl-6-(morpholin-4-yl)-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles.     

Two directions of interaction of 2-aryl-1,2,3,4-tetrahydropyridine-3,3,4,4-tetracarbonitriles with nucleophiles

Depending on the reaction conditions, 2-aryl-1,2,3,4-tetrahydropyridine-3,3,4,4-tetracarbonitriles react with alcohols, thiols and ketoximes to give 3-amino-4-aryl-1,1-di[R-oxy(thio)]-6,7-dialkyl-3a,4,5,7a-tetrahydro-1H-pyrrolo[3,4-c]pyridine-3a, 7a-dicarbonitrles or 2-aryl-5,6-dialkylpyridine-3,4-dicarbonitriles.Chuvash State University, Cheboksary 428015. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 367–375, March, 1997.