Tetrahedron Letters

High-temperature continuous flow synthesis of 1, 3, 4-oxadiazoles via N-acylation of 5-substituted tetrazoles

B Reichart, CO Kappe

Index: Reichart, Benedikt; Kappe, C. Oliver Tetrahedron Letters, 2012 , vol. 53, # 8 p. 952 - 955

Full Text: HTML

Citation Number: 16

Abstract

Applying continuous flow processing in a high-temperature/high-pressure regime (200–220° C, 11–14bar) 2, 5-disubstituted-1, 3, 4-oxadiazoles are prepared in high yields within 5– 10min residence time by treatment of 5-substituted-1H-tetrazoles with anhydrides or acid chlorides as electrophiles (Huisgen reaction).

Related Articles:

Visible-light-promoted aerobic oxidative cyclization to access 1, 3, 4-oxadiazoles from aldehydes and acylhydrazides

[Yadav, Arvind K.; Yadav, Lal Dhar S. Tetrahedron Letters, 2014 , vol. 55, # 13 p. 2065 - 2069]

2-Chloro-1, 3-dimethylimidazolinium chloride. 2. Its application to the construction of heterocycles through dehydration reactions

[Isobe, Toshio; Ishikawa, Tsutomu Journal of Organic Chemistry, 1999 , vol. 64, # 19 p. 6989 - 6992]

A mild and efficient one pot synthesis of 1, 3, 4-oxadiazoles from carboxylic acids and acyl hydrazides

[Rajapakse, Hemaka A.; Zhu, Hong; Young, Mary Beth; Mott, Bryan T. Tetrahedron Letters, 2006 , vol. 47, # 28 p. 4827 - 4830]

A mild and efficient one pot synthesis of 1, 3, 4-oxadiazoles from carboxylic acids and acyl hydrazides

[Rajapakse, Hemaka A.; Zhu, Hong; Young, Mary Beth; Mott, Bryan T. Tetrahedron Letters, 2006 , vol. 47, # 28 p. 4827 - 4830]

More Articles...