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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.
Heteroatom Chemistry – Wiley
Published: Jan 1, 1997
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