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A Click Chemistry Approach to Tetrazoles by Huisgen 1,3‐Dipolar Cycloaddition: Synthesis of 5‐Acyltetrazoles from Azides and Acyl Cyanides
Author(s) -
Demko Zachary P.,
Sharpless K. Barry
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020617)41:12<2113::aid-anie2113>3.0.co;2-q
Subject(s) - cycloaddition , click chemistry , chemistry , alkyl , organic chemistry , 1,3 dipolar cycloaddition , combinatorial chemistry , yield (engineering) , catalysis , materials science , metallurgy
Click chemistry : Acyl cyanides react with alkyl azides in high yield by heating at 120–130°C (see scheme). The reactions are run neat, and the workup is simple. When p ‐nitrophenyl cyanoformate is used as the dipolarophile, the resulting tetrazoles are activated for rapid functionalization as an activated ester.