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Thermal transformation of arylamidoximes in the presence of phosphorus ylides. Unexpected formation of 3‐aryl‐5‐arylamino‐1,2,4‐oxadiazoles
Author(s) -
Nicolaides Demetrios N.,
Litinas Konstantinos E.,
Vrasidas Ioannis,
Fylaktakidou Konstantina C.
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410404
Subject(s) - chemistry , aryl , phosphorane , nitrogen atom , cyanide , carbon atom , crystal structure , medicinal chemistry , nitrogen , phosphorus , atom (system on chip) , organic chemistry , ring (chemistry) , alkyl , computer science , embedded system
Abstract The unexpected formation of 3‐aryl‐5‐arylamino‐1,2,4‐oxadiazoles took place, when arylamidoximes reacted thermally with ethoxycarbonylmethylene(triphenyl)phosphorane. Furoxans, nitriles, ureas were also isolated suggesting aryl cyanide oxides as intermediates. 3‐Aryl‐5‐arylamino‐1,2,4‐oxadiazoles were formed via an aryl migration from the carbon atom to the nitrogen atom of the amidoxime, and the structure was further proved from the X‐ray crystal structure of the N ‐(4‐bromobenzoyl) derivative.