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Pyrolysis and photolysis of 1‐aroylamino‐4,5‐diaryl‐1,2,3‐triazoles: Generation and thermal transformations of 4,5‐diaryl‐1,2,3‐triazolyl radicals
Author(s) -
HadjiantoniouMaroulis C. P.,
Charalambopoulos A. Ph.,
Maroulis A. J.
Publication year - 1998
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.5570350418
Subject(s) - chemistry , radical , benzamide , hydrogen atom abstraction , triazole , photodissociation , pyrolysis , photochemistry , aryl , medicinal chemistry , organic chemistry , alkyl
The pyrolysis of 1‐aroylamino‐4,5‐diphenyl‐1,2,3‐triazoles 1 yields, pressumably via the 4,5‐diphenyl‐1,2,3‐triazolyl radical ( 2a ), 2,3‐diphenyl‐2 H ‐azirine ( 11a ) and 2‐aryl‐4,5‐diphenylimidazoles 14 as the major products. Upon irradiation 1‐benzoylamino‐4,5‐diphenyl‐1,2,3‐triazole ( 1a ) gives 4,5‐diphenyl‐1 (2) H ‐1,2,3‐triazole ( 4a ) via the 1,2,3‐triazolyl radical 2a , together with benzamide ( 5a ) and 1,2‐bisbenzoylhydrazine ( 6a ). Products 5a and 6a result from the benzoylamino radical 3a by hydrogen atom abstraction and dimerization respectively.