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

Triazolo[4,3-<i>a</i>]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-<i>a</i>]pyrimidine, which are syntheti...

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Main Authors: Artem S. Agarkov, Dilyara O. Mingazhetdinova, Anna A. Nefedova, Alexander S. Ovsyannikov, Andrey K. Shiryaev, Igor A. Litvinov, Svetlana E. Solovieva, Igor S. Antipin
Format: Article
Language:English
Published: MDPI AG 2023-08-01
Series:Organics
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Online Access:https://www.mdpi.com/2673-401X/4/3/31
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Summary:Triazolo[4,3-<i>a</i>]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-<i>a</i>]pyrimidine, which are synthetic precursors for triazolo[4,3-<i>a</i>]pyrimidines. The crystal structure of 6-acetyl-7-methyl-5-phenyl-2-(2-phenylhydrazineylidene)-5<i>H</i>-thiazolo[3,2-<i>a</i>]pyrimidin-3(2<i>H</i>)-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 (1<i>R*</i>)-1-((5<i>S*</i>,6<i>R*</i>,7<i>R*</i>)-(1-(hydroxymethyl)-7-methyl-1,5-diphenyl-1,5,6,7-tetrahydro[1,2,4]triazolo[4,3-<i>a</i>]pyrimidin-6-yl)ethan-1-ol.
ISSN:2673-401X