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Synthesis and Structure of 6-Acetyl-2-Arylhydrazone Derivatives of Thiazolo[3,2-a]Pyrimidine

Artem S. Agarkov, Dilyara O. Mingazhetdinova, Anna A. Nefedova, Alexander S. Ovsyannikov, Andrey K. Shiryaev, Igor A. Litvinov, Svetlana E. Solovieva, Igor S. Antipin

Organics · pp. 438–446 · Published 11 Aug 2023

10.3390/org4030031

Abstract

Triazolo[4,3-a]pyrimidine is one of the promising structural fragments for the development of drugs, including anticancer drugs. This work is devoted to the synthesis of a number of new 2-arylhydrazone derivatives of thiazolo[3,2-a]pyrimidine, which are synthetic precursors for triazolo[4,3-a]pyrimidines. The crystal structure of 6-acetyl-7-methyl-5-phenyl-2-(2-phenylhydrazineylidene)-5H-thiazolo[3,2-a]pyrimidin-3(2H)-one was established by SCXRD. In the reduction reaction of the compound, the following system was used: vanadium(V) oxide, and sodium borohydride in ethanol at room temperature, which led to the formation of only one pair of diastereomers (1R*)-1-((5S*,6R*,7R*)-(1-(hydroxymethyl)-7-methyl-1,5-diphenyl-1,5,6,7-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidin-6-yl)ethan-1-ol.

Pyrimidine Chemistry Sodium borohydride Hydroxymethyl Diastereomer Stereochemistry Crystal structure Vanadium

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