L. D. Konyushkin

Synthesis and structures of 4,6-disubstituted 2-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

New 1,2,4-oxadiazolyl-1,3,5-triazines were synthesized from amidoximes derived from sym-triazine mononitriles. The structure of one of the resulting compounds was studied in detail by X-ray diffraction.

Synthesis of substituted benzoxazinylthieno [2,3-b]pyridines by the reaction of (3-cyanopyridin-2-ylthio)acetic acids or their amides with o-aminophenyl(diphenyl)carbinol

A general method for the synthesis of 3-amino-2-(4,4-diphenyl-4H-3,1-benzoxazin-2-yl)thieno[2,3-b]pyridines was proposed. The method involves reactions of (3-cyanopyridin-2-ylthio)acetic acids or their amides with o-aminophenyl(diphenyl)carbinol in nitromethane in the presence of perchloric acid followed by neutralization of the resulting salts.

Synthesis of 4-amino-substituted but-2-en-4-olides

Previously unknown 4-amino derivatives of spiro-annelated Δ2-butenolide were synthesized by the addition of various amines at the activated triple bond of 4-hydroxy-2-alkynoic esters.

ELECTROCHEMICAL SYNTHESIS AND STUDIES OF SUBSTITUTED 2-THIOPYRIDINES

A series of substituted 2-alkyl(aryl-, hetaryl-)thiopyridines was prepared by cathodic electrolysis of thiols in the presence of 2-chloro-3-cyano-4-methoxymethyl-6-methylpyridine or 4-chloro-6-methyl-3-oxo-1H-furo[3,4-c]pyridine. The reaction of 3-cyano-4-methoxymethyl-6-methyl-2(1H)-thiopyridone with alkyl halides in the presence of KOH is regioselective and leads toS-alkyl derivatives. The advantages of electrosynthesis for the preparation of 2-alkylthiopyridines fused with 2(5H)-furanone and of 3-aminothieno [2,3-b]pyridines is demonstrated.

Cathode generation of thiolate anions and the correlation between their oxidationE1/2 and nucleophilic reactivity

Cathode reduction of a series of aliphatic, aromatic, and heteroaromatic thiols on a rotating disk Pt electrode in abs. MeCN against the background of 0.1N Bu4NClO4 was investigated. It was found that this process results in the formation of the corresponding thiolate anions whose oxidation half-wave potentials are linearly correlated with their nucleophilicity in theSN 2 reaction.

Electrochemical synthesis of functionally substituted sulfides

A method of synthesis of functionally substituted sulfides by cathode electrolysis of thiols on platinum or carbon glass electrodes in the presence of organyl halides was developed. The method of the rotating disk electrode with ring showed that this process passes through the intermediate formation of a thiolate anion on the cathode, and its reaction with the organyl halide results in a high yield of sulfides.