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Synthesis 2024; 56(14): 2284-2294
DOI: 10.1055/a-2017-4814
DOI: 10.1055/a-2017-4814
paper
Regio- and Diastereoselective Synthesis of Substituted Triazolo [3,4-b]thiadiazin-6-ols and Triazolo[3,4-b]thiadiazines
We are grateful to the Faculty of Chemistry of Kharazmi University for supporting this work. We also thank the Alexander von Humboldt Foundation for supporting this work.
Abstract
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 °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 α-((4-amino-5-methyl-4H-1,2,4-triazol-3-yl)thio)-α-phenylpropan-2-one in quantitative yield.
Key words
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-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2017-4814.
- Supporting Information
Publication History
Received: 16 March 2022
Accepted after revision: 22 January 2023
Accepted Manuscript online:
22 January 2023
Article published online:
15 February 2023
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