Polar effects in free??radical reactions. A novel homolytic acylation of heteroaromatic bases by aerobic oxidation of aldehydes, catalysed by N??hydroxyphthalimide and …
F Minisci, F Recupero, A Cecchetto…
Index: Minisci, Francesco; Recupero, Francesco; Cecchetto, Andrea; Punta, Carlo; Gambarotti, Cristian; Fontana, Francesca; Pedulli, Gian Franco Journal of Heterocyclic Chemistry, 2003 , vol. 40, # 2 p. 325 - 328
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Citation Number: 24
Abstract
Abstract A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N-oxyl radical (PINO) generated from N-hydroxyphthalimide by air oxygen and Co (II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearo-matised in a chain process. Quinazoline has an anomalous behaviour, giving 3H-quinazolin-4-one as the only ...
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