Regio- and Diastereoselective Synthesis of Substituted Triazolo [3,4-b ]thiadiazin-6-ols and Triazolo[3,4-b ]thiadiazines

被引：4

作者：

Mohammadlou, Mahsa ^{[1
]}

Halimehjani, Azim Ziyaei ^{[1
,2
]}

机构：

[1] Kharazmi Univ, Fac Chem, POB 15719-14911,49 Mofateh St, Tehran, Iran

[2] Sharif Univ Technol, Dept Chem, POB 11155-9516, Tehran, Iran

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 14期

关键词：

nitroepoxide; 6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazin-6-ols; 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines; diastereoselective??????; catalyst-free; BIOLOGICAL EVALUATION; DERIVATIVES; NITROEPOXIDES; ANTIBACTERIAL; HETEROCYCLES;

D O I：

10.1055/a-2017-4814

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, catalyst-free, regio-and diastereoselective approach for the synthesis of novel 7-aryl-3-alkyl(aryl)-6-methyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-ols has been developed via the reaction of 4-amino-[1,2,4]triazole-3-thiols with nitroepoxides in methanol at room temperature. The products were simply dehydrated in the presence of PTSA in ethanol at 70 degrees C to afford the corresponding 7-aryl-3-alkyl(aryl)-6-methyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines in 91-98% yields. In addition, treatment of the product with acidic chloroform afforded the corresponding alpha-((4-amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)-alpha-phenylpropan-2-one in quantitative yield.

引用

页码：2284 / 2294

页数：11

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