Alexander V. Shevtsov

Reaction of 1,2-dialkyldiaziridines with ketenes as a new approach to cyclic and linear systems containing the N— C—N fragment

The reaction of 1,2-dialkyldiaziridines with ketenes proceeds through the N—N bond cleavage to form three types of structures containing the N—C—N fragment, viz., 1,3-dialkylimidazolidin-4-ones, 3,5-diacyl-3,5-diazahept-1-enes, and β-lactams. The reaction pathway depends on the reaction conditions and the structures of the starting compounds.

Synthesis of 4-aroyl-1,2,4-triazolidin-3-ones via ring extension in reactions of 1,2-di- and 1,2,3,3-tetraalkyldiaziridines with aroyl isocyanates

Reactions of 1,2-di-and 1,2,3,3-tetraalkyldiaziridines with aroyl isocyanates involve opening of the diaziridine ring through cleavage of the C—N bond followed by cyclization of the zwitterionic intermediate into 4-aroyl-1,2,4-triazolidin-3-one derivatives.

Synthesis and structures of complexes ofN-(2-aminoethyl)diaziridines with transition metal salts

A series of complexes ofN-(2-aminoethyl)diaziridines with transition metal salts (Zn2+, Cd2+, Ni2+, Co2+, Mn2+, or Fe2+) were synthesized. Their structures were established by IR and NMR spectroscopy. The structure of bis[1,2-bis(2-aminoethyl)diaziridine]cadmium(II) diperehlorate was confirmed by X-ray diffraction analysis.

Synthesis of 1,3,5-triazabicyclo[3.1.0]hexanes containing the fragments of α-amino acids and their esters at the N(3) atom

With 3,3-pentamethylene-1,2H-diaziridine as an example, it was shown that 3,3-dialkyl-1,2H-diaziridines can undergo cyclocondensation with α-amino acids and their esters to give the corresponding N(3)-substituted 1,3,5-triazabicyclo[3.1.0]hexanes, including pure enantiomers.

Diastereoselective synthesis of substituted 1,3,6-triazabicyclo[3.1.0]hexanes

A general method was developed for the synthesis of substituted 1,3,6-triazabicyclo[3.1.0]hexanes via intramolecular aminomethylation of the NH group of the diaziridine ring by the reactions of 3-aminomethyl-1,3-dimethyldiaziridine with aliphatic, aromatic, and heteroaromatic carbonyl compounds. These reactions with aldehydes proceeded diastereoselectively to form mixtures of two racemates, viz., 1R*,2R*,5R*,6R* and 1R*,2S*,5R*,6R*, in a ratio of (3—20) : 1, the predominant diastereomer being isolated in all cases. The reactions with symmetrical ketones gave rise exclusively to the (1R*,5R*,6R*) racemate. The predominant diastereomer 1R*,2R*,5R*,6R*-2-(2-bromothien-5-yl)-1,3,6-triazabicyclo[3.1.0]hexane crystallized as a conglomerate. The structure of one of its enantiomers was established by X-ray diffraction analysis.