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Reaction of 5‐Amino‐4,5‐dihydro‐4‐methylene‐1,2,3‐triazoles with 2,4‐Diaryl‐5(4 H )‐oxazolon‐4‐yl Radicals
Author(s) -
Arlandini Emaanule,
Clerici Francesca,
Erba Emanuela,
Rossi Luisa Maria
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901230136
Subject(s) - chemistry , radical , methylene , nucleophile , dissociation (chemistry) , medicinal chemistry , ion , organic chemistry , catalysis
When bioxazolones 2 are treated at high temperature with 5‐amino‐4,5‐dihydrotriazoles, 3 , the corresponding triazolylmethyl‐5(4 H )‐oxazolones 4 and 5 are produced by dissociation of 2 into oxazolonyl radicals and reaction of these with 3 , followed by transfer a hydrogen or morpholinyl radical. Products 4 and 5 ar also formed starting form 3 and 5(4 H )‐oxazolones 1 , which are oxidized during the reaction to the corresponding bioxazolone 2 , In this case, besides products 4 and 5 , the corresponding triazolymethyl‐5(4 H )‐oxazolones 6 are also formed, presumably by nucleophilic attack of the anion of 1 on substrate 3 .