S. E. Sosonyuk

Synthesis of novel МТ3 receptor ligands via an unusual Knoevenagel condensation

New 5-acetamido-substituted melatonin derivatives were efficiently synthesized in excellent yields via Knoevenagel condensation. The relative binding affinity of new synthesized compounds to MT3 receptor was tested via enzymatic assays and the X-ray structures of the most potent compounds were determined in complex with MT3.

New electrophilic iodochlorinating systems based on iodine (+1)

Two new convenient systems for electrophilic iodochlorination of olefins are proposed: KIO3+I2+HCl (in aqueous solutions) and KlCl4+I2 (in organic solvents).

Nucleophilic Opening of the Aziridine Ring in 1-Alkyl-1-azoniatricyclo[2.2.1.02,6]heptanes

Opening of the aziridine ring in 3-bromo-1-alkyl-1-azoniatricyclo[2.2.1.02,6]heptane bromides by the action of various nucleophiles leads to formation of the corresponding 6-substituted 2-alkyl-2-azabicyclo[2.2.1]heptanes.

Halogenation of 2-alkyl-2-azabicycloalkenes as a method for the synthesis of stable aziridinium salts of a new class

Addition of bromine and potassium dihaloiodates(i) to 2-alkyl-2-azabicyclo[2.2.1]hept-5-enes and 2-alkyl-2-azabicyclo[2.2.2]oct-5-enes affords quaternary ammonium salts containing the aziridine ring and the polyhalide anion. The possibility of using these salts for the synthesis of 6-substituted 2-alkyl-2-azabicyclo[2.2.1]heptanes has been shown.

Iodosulfenylation of olefins with sulfenamides in the presence of metal iodides

Reactions of arylsulfenamides, arylsulfenates, thiobisamines, and dithiobisamines with olefins in the presence of zinc, tin(ii), tin(iv), antimony(iii), or magnesium iodides were investigated. In the case of cage olefins, the reactions afford mixtures of 1,2-iodosulfides and diiodides, the ratio between which depends on the type of iodine-containing Lewis acid. lodosulfides were obtained in the highest yields in the reactions of cage olefins upon activation with zinc or tin(ii) iodides. In the case of olefins prone to the Wagner—Meerwein rearragement (bicyclo[2.2.1]heptanes) or to the addition—elimination reaction (camphene), the corresponding products formed. A reaction mechanism is proposed.

Preparative successive generation of dehydrobenzene intermediate from 2,5-Bis(trimethylsilyl)-1,4-phenylene bis(trifluoromethanesulfonate) and its cycloaddition reactions

Abstract A method of preparative successive cycloaddition to synthetic equivalent of bis(dehydrobenzene) was found. Monoaddition products were isolated and characterized.

Synthesis of 1,3,5-Tribromo- and Triiodophloroglucinol Tris(triflates)

A method for the preparative synthesis of 1,3,5-tribromophloroglucinol and 1,3,5-triiodophloroglucinol tris(triflates) was suggested. This synthesis was shown to be extremely sensitive to reaction temperature conditions.

Synthesis of N-(2,2,2-trichloro-1-hydroxyethyl)aldimines and their derivatives

The preparative procedure for the synthesis of N-(2,2,2-trichloro-1-hydroxyethyl)aldimines from the corresponding aldehyde, chloral, and ammonium acetate was developed. Preparative silylation and acylation of their hydroxy groups were acomplished for the first time. The possibility to use the synthesized O-trimethylsilyl and O-acetyl derivatives as the synthetic equivalents of N-nonsubstituted imines in the reactions with cyclopropenone was investigated.

Homocoupling of bromotriazole derivatives on metal complex catalysts

Homocoupling of 4-bromo-1,2,3-triazoles upon treatment with stoichiometric amount of bis(pinacolato)diboron on a palladium catalyst gives 4,4´-bi-1,2,3-triazoles in up to 95% yields.

Stable synthetic equivalents of N-unsubstituted imines: Part 1. Synthesis

The key role of imines in organic synthesis, for example in the synthesis of amine derivatives and nitrogen heterocycles, is well known. However, the instability of N-unsubstituted imines is often an obstacle to the selection of synthesis strategy. Therefore, it is rather topical to design stable imines with a readily removable group at the nitrogen atom. The first part of this review deals with the methods of synthesis of N-sulfinyl imines (including chiral), N-sulfonyl imines, N-phosphinoyl imines, N-acylimines, N-silylimines, N-(hexopyranosyl)imines, N-benzylimines, N-(methoxyphenyl)imines, N-allylimines, 1,3,5-trisubstituted 2,4-diazapenta-1,4-dienes, and N-(1-hydroxyethyl-2,2,2-trichloro)imines and the methods for removing these protective groups.