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

被引：3

作者：

Agarkov, Artem S. ^{[1
]}

Mingazhetdinova, Dilyara O. ^{[2
]}

Nefedova, Anna A. ^{[1
]}

Ovsyannikov, Alexander S. ^{[1
]}

Shiryaev, Andrey K. ^{[3
]}

Litvinov, Igor A. ^{[1
]}

Solovieva, Svetlana E. ^{[1
]}

Antipin, Igor S. ^{[2
]}

机构：

[1] Russian Acad Sci, Arbuzov Inst Organ & Phys Chem, FRC Kazan Sci Ctr, Arbuzova 8, Kazan 420088, Russia

[2] Kazan Fed Univ, AM Butlerov Chem Inst, 18 Kremlevskaya St, Kazan 420008, Russia

[3] Samara State Tech Univ, Dept Chem, Molodogvardeyskaya 244, Samara 443100, Russia

来源：

ORGANICS | 2023年 / 4卷 / 03期

关键词：

thiazolo[3,2-a]pyrimidines; hydrazine derivatives; triazolo[4,3-a]pyrimidines; crystal structure; hydrogen bonding; intramolecular rearrangement; reduction; diastereoselectivity; PYRIMIDINE-DERIVATIVES; BIOLOGICAL EVALUATION; DESIGN;

D O I：

10.3390/org4030031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：438 / 446

页数：9

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