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

Author:

Agarkov Artem S.1ORCID,Mingazhetdinova Dilyara O.2ORCID,Nefedova Anna A.1,Ovsyannikov Alexander S.1ORCID,Shiryaev Andrey K.3,Litvinov Igor A.1,Solovieva Svetlana E.1ORCID,Antipin Igor S.2

Affiliation:

1. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Arbuzova 8, 420088 Kazan, Russia

2. A.M. Butlerov Chemical Institute, Kazan Federal University, 18 Kremlevskaya St., 420008 Kazan, Russia

3. Department of Chemistry, Samara State Technical University, Molodogvardeyskaya 244, 443100 Samara, Russia

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.

Funder

Arbuzov Institute of Organic and Physical Chemistry

Publisher

MDPI AG

Subject

Industrial and Manufacturing Engineering

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