2-Azido-1,3,4-thiadiazoles, 2-Azido-1,3-thiazoles, and Aryl Azides in the Synthesis of 1,2,3-Triazole-4-carboxylic Acids and Their Derivatives

Diazotization of 2-amino-1,3,4-thiadiazoles gave 1,3,4-thiadiazole-2-diazonium sulfates which were converted to 2-azido-1,3,4-thiadiazoles. The latter reacted with ethyl acetoacetate in the presence of sodium methoxide in methanol to produce 1-(5-R 1 -1,3,4-thiadiazol-2-yl)-5-R 2 -1 H -1,2,3-triazol...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 54; no. 7; pp. 1090 - 1099
Main Authors Pokhodylo, N. T., Shyyka, O. Ya, Savka, R. D., Obushak, M. D.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.07.2018
Springer Nature
Springer Nature B.V
Subjects
Aromatic compounds
Carboxylic acids
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Derivatives
Organic Chemistry
Physical Sciences
Potassium carbonate
Science & Technology
Thiadiazoles
REACTIVITY
SYSTEMS
AZEPINES
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Summary:Diazotization of 2-amino-1,3,4-thiadiazoles gave 1,3,4-thiadiazole-2-diazonium sulfates which were converted to 2-azido-1,3,4-thiadiazoles. The latter reacted with ethyl acetoacetate in the presence of sodium methoxide in methanol to produce 1-(5-R 1 -1,3,4-thiadiazol-2-yl)-5-R 2 -1 H -1,2,3-triazole-4-carboxylic acid derivatives. The reactions of 2-azido-5-methyl-1,3,4-thiadiazole and 2-azido-1,3-thiazole with ethyl 3-(1,3-benzodioxol-5-yl)-3-oxopropanoate led to the formation of 1,2,3-triazole ring under milder conditions (K 2 CO 3 , DMSO). Various 1,2,3-triazole-4-carboxylic acid derivatives were synthesized.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428018070205