V. A. Tafeenko

First synthesis of adamantylated thiacalix[4]arenes

p-(1-Adamantyl)thiacalix[4]arene was synthesized both by condensation of p-(1-adamantyl)phenol with sulfur in the presence of NaOH and by alkylation of p-H-thiacalix[4]arene with 1-adamantanol in trifluoroacetic acid. Using the latter method, the first thiacalix[4]arene carboxylated at the upper rim was obtained from p-H-thiacalix[4]arene and 3-carboxy-1-adamantanol. The X-ray structural analysis revealed that p-(1-adamantyl)thiacalix[4]arene adopts a cone conformation leading to an inclusion complex with chloroform under the conditions of crystallization.

(CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones

Summary A very simple and convenient reaction for 1,3-diketone preparation from carboxylic acids and aromatic ketones in TFAA/TfOH system is described. When the β-phenylpropionic acids were used as starting materials, they initially gave 1-indanones and then underwent further acylation with the formation of 2-(β-phenylpropionyl)-1-indanones as the main reaction products. In addition, the application of the proposed protocol allowed for the synthesis of selected polysubstituted pyrazoles in a one-pot procedure directly from acids and ketones.

New push–pull chromophores. Synthesis of 2-[4-Aryl-3-cyano-5-hydroxy-5-methyl-1H-pyrrol-2(5H)-ylidene]malononitriles

Abstract2-Aminoprop-1-ene-1,1,3-tricarbonitrile (malononitrile dimer) reacted with 1-arylpropane-1,2-diones in ethanol in the presence of piperidine to give new donor–acceptor chromophores, 2-[4-aryl-3-cyano-5-hydroxy-5-methyl-1H-pyrrole-2(5H)-ylidene]malononitriles.

Selective quasi-hydrolysis of cyano group in 6-hydroxypiperidine-3,4,4-tricarbonitriles

Reactions of 3,3-dialkyl-4-oxoalkane-1,1,2,2-tetracarbonitriles with water in the presence of pyruvic acid are accompanied by selective quasi-hydrolysis of cyano groups in intermediate 6-hydroxypiperidine-3,4,4-tricarbonitriles.

Transformations of 3,3,4-tricyano-3,4-dihydro-2 H -pyran-4-carboxamides. Synthesis of pyrano[3,4- c ]pyrrole derivatives

A procedure has been developed for the synthesis of polyfunctional pyrano[3,4-c]pyrrole derivatives via intramolecular cyclization involving vicinal cyano and carboxamide groups on a pyran ring. 3-Amino-1-oxo-1,3a,4,7a-tetrahydropyrano[3,4-c]pyrrole-3a,7a-dicarbonitrile thus obtained react with organic amines to give stable ammonium salts and undergo hydrolysis to 1,3-dioxo-1,2,3,3a,4,7a-hexahydropyrano[3,4-c]pyrrole-3a,7a-dicarbonitriles in the presence of sulfuric acid.

Synthesis of 9-alkyl-8-methoxy-8-methyl-1,3,6-trioxo-2,7-diazaspiro[4.4]nonane-4-carbonitriles

A method of synthesis of 9-alkyl-8-methyl-8-methoxy-1,3,6-trioxo-2,7-diazaspiro[4.4]nonane-4-carbonitriles consisting in the reaction of 3-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with methanol in the presence of sulfuric acid was developed.

N -acylimino-substituted 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes in the synthesis of 3-(1 H -1,2,4-triazol-3-yl)-3 H -pyrrole-4-carbonitriles

Reaction with phenylhydrazine of 3Н-pyrroles spirobound to a furan ring, N-acylimino-substituted 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes, occurs with a diasteroselective formation of previously unknown derivatives of 1,2,4-triazole: 5-amino-3-(5-alkyl-1-phenyl-1H-1,2,4-triazol-3-yl)-2-morpholin-4-yl-3H-pyrrole-4-carbonitriles.

Synthesis of 4-halo-3-(phenylamino)furo[3,4- c ]pyridin-1(3 H )-ones

A method was developed for the synthesis of 4-halo-3-(phenylamino)-furo[3,4-c]pyridin-1(3H)-ones by the reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with aniline at room temperature.