S. A. Chumachenko

Recyclization of 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile by benzylamine, phenethylamine, and phenylhydrazine

Reaction of 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile with benzylamine, phenethylamine and phenylhydrazine results in the new substituted 5-amino-2,3-dihydro-1H-imidazol-2-ones.

Reactions of N-(2,2-dichloro-1-cyanoethenyl)-N′-methyl(phenyl)ureas with aliphatic amines

Novel derivatives of 3,3-dichloroprop-2-enenitrile containing methylurea or phenylurea fragments have been synthesized. The obtained N-(2,2-dichloro-1-cyanoethenyl)-N′-methyl(phenyl)ureas undergo intramolecular cyclization in the presence of triethylamine to form 4-(dichloromethylidene)-5-imino-1-methyl (phenyl)imidazolidin-2-ones. Reactions of N-(2,2-dichloro-1-cyanoethenyl)-N′-methylurea with aliphatic amines have afforded 4-(alkylamino)-4-(dichloromethyl)-5-imino-1-methylimidazolidin-2-ones.

Synthesis of new substituted 5-amino-1H-imidazole-4-carbonitriles

A series of new 5-amino-1H-imidazole-4-carbonitriles were synthesized based on substituted 3,3-di-amino-2-methylideneaminoprop-2-enenitriles.

Interaction of 5-(Morpholin-4-Yl)-2-(4-Phthal-Imidobutyl)- and 5-(Morpholin-4-Yl)-2-(5-Phthal-Imidopentyl)-1,3-Oxazole-4-Carbonitriles with Hydrazine Hydrate

5-Morpholino-1,3-oxazole-4-carbonitriles bearing 4-phthalimidobutyl or 5-phthalimidopentyl substi-tuent at position 2 of the oxazole ring were synthesized. Upon reaction with hydrazine hydrate, 5-(morpholin-4-yl)-2-(4-phthalimidobutyl)-1,3-oxazole-4-carbonitrile formed the recyclization product (3-amino-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)(morpholin-4-yl)methanone, whereas for 5-(morpholin-4-yl)-2-(5-phthalimidopentyl)-1,3-oxazole-4-carbonitrile, the reaction stops at the stage of 2-(5-aminopentyl)-5-(morpholin-4-yl)-1,3-oxazole-4-carbonitrile after removal of the phthalimido protecting group.

Application of the Recyclization Products of 5-Alkyl(aryl)amino-2-(3-phthalimidopropyl)-1,3-oxazole-4-carbonitriles to the Synthesis of Condensed Tricyclic Nitrogenous Structures

N-Alkyl(aryl)-3-amino-5H,6H,7H-pyrrolo[1,2-a]imidazole-2-carboxamides were obtained by the interaction of 5-alkyl(aryl)amino-2-(3-phthalimidopropyl)-1,3-oxazole-4-carbonitriles with hydrazine hydrate and have been used for the synthesis of substituted 3H,4H,6H,7H,8H-pyrrolo[2,1-h]purin-4-ones, their thione analogs, and also 1,2,3,6,7,8-hexahydro-4H-pyrrolo[2′,1′:2,3]imidazo[4,5-d]-[1,3,2]diazaphosphinine derivatives.

Reaction of 1-alkyl(aryl)-5-alkyl(aryl)amino-2-oxo-2,3-dihydro-H-imidazole-4-carbonitriles with Lawesson’s reagent

The reaction of substituted 2-oxo-2,3-dihydro-1H-imidazole-4-carbonitriles with Lawesson’s reagent gave new compounds of the fused imidazo[4,5-d][1,3,2]diazaphosphinine system.

Formation of 3-acylamino-2-arylhydrazono-3-cyano-2,3-dihydro-1H-indoles in the reaction of 2-acylamino-3,3-dichloroacrylonitriles with arylhydrazines

The reaction of 2-acylamino-3,3-dichloroacrylonitriles with arylhydrazines in tetrahydrofuran upon heating was investigated. It led to previously unknown 3-acylamino-2-arylhydrazono-3-cyano-2,3-di-hydro-1H-indoles.

Reaction of 2-acylamino-3,3-dichloroacrylonitriles with 2-aminothiophenol

Reactions of 2-acylamino-3,3-dichloroacrylonitriles with 2-aminothiophenol in the presence of triethylamine was shown to lead to 2-aryl-3,3-bis(2-aminophenylsulfanyl)acrylonitrile, which suffered a transformation into 5-amino-4-(benzothiazol-2-yl)oxazole derivatives at heating without solvent. The formation of the same compounds from these reagents proceeded in one step in the presence of N,N-dimethylaniline. The presence of primary amino groups in the derivatives of 5-aminooxazole was confirmed by acylation and further transformation, which was used also for indroduction of various biophoric sites in 5 position of the oxazole ring.