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Thermolysis of 3‐phenyl‐5‐arylamino‐1,2,4‐oxadiazole and thiadiazole derivatives

Thermolysis of 3‐phenyl‐5‐arylamino‐1,2,4‐oxadiazole and thiadiazole derivatives Thermal reactions of 3‐phenyl‐5‐arylamino‐1,2,4‐oxadiazoles I and II were investigated. Neat heating at ca. 250°C for 6 hours afforded H2O, benzonitrile, arylcyanamides, arylamines, azobenzene, benzimidazole derivatives, and 3,3′‐diphenyl‐5,5′‐bis[1,2,4‐oxadiazolyl]. Analogous results were obtained by the thermolysis of 3‐phenyl‐5‐anilino‐1,2,4‐thiadiazole III at ca. 200°C for 2 hours. In addition to H2S, NH3, and HNCS, phenyl isothiocyanate and thiocarbanilide were obtained. Thermolysis of III in quinoline as a radical trap gave analogous resuLts but also 2‐anilinoquinoline. A free‐radical mechanism has been suggested to account for the identified products. © 1997 John Wiley & Sons, Inc. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Thermolysis of 3‐phenyl‐5‐arylamino‐1,2,4‐oxadiazole and thiadiazole derivatives

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References (14)

Publisher
Wiley
Copyright
Copyright © 1997 Wiley Subscription Services
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/(SICI)1098-1071(1997)8:4<287::AID-HC1>3.0.CO;2-8
Publisher site
See Article on Publisher Site

Abstract

Thermal reactions of 3‐phenyl‐5‐arylamino‐1,2,4‐oxadiazoles I and II were investigated. Neat heating at ca. 250°C for 6 hours afforded H2O, benzonitrile, arylcyanamides, arylamines, azobenzene, benzimidazole derivatives, and 3,3′‐diphenyl‐5,5′‐bis[1,2,4‐oxadiazolyl]. Analogous results were obtained by the thermolysis of 3‐phenyl‐5‐anilino‐1,2,4‐thiadiazole III at ca. 200°C for 2 hours. In addition to H2S, NH3, and HNCS, phenyl isothiocyanate and thiocarbanilide were obtained. Thermolysis of III in quinoline as a radical trap gave analogous resuLts but also 2‐anilinoquinoline. A free‐radical mechanism has been suggested to account for the identified products. © 1997 John Wiley & Sons, Inc.

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 1997

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