AN IMPROVED PROCEDURE FOR THE PREPARATION OF 1-BENZYL-1H-1,2,3-TRIAZOLES FROM BENZYL AZIDES

A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described. The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used. Benzyl azides...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 28; no. 2; pp. 301 - 304
Main Authors COTTRELL, IF, HANDS, D, HOUGHTON, PG, HUMPHREY, GR, WRIGHT, SHB
Format Journal Article
LanguageEnglish
Published TAMPA HETERO CORPORATION 01.02.1991
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC AZIDES
KETONES
1,2,3-TRIAZOLES
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Summary:A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described. The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used. Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35-40-degrees to give 1H-1,2,3-triazoles usually in good yield. Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and beta-diketones respectively. Benzyl methyl ketone reacted to give a 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react. Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate.
ISSN:0022-152X
DOI:10.1002/jhet.5570280216