Homolytic acylation of protonated pyridines and pyrazines with. alpha.-keto acids: the problem of monoacylation

…, MC Nogueira Barbosa, E Vismara

Index: Fontana, Francesca; Minisci, Francesco; Barbosa, Maria Claudia Nogueira; Vismara, Elena Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2866 - 2869

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Citation Number: 116

Abstract

The silver-catalyzed decarboxylation of a-keto acids by persulfate leads to acyl radicals, which can effect the selective homolytic acylation of pyridine and pyrazine derivatives. Compared with the previously developed source of acyl radicals by hydrogen abstraction from aldehydes, this procedure is more effective in monoacylation when multiple positions of high nucleophilic reactivity are available in the heterocyclic ring. Although the introduction ...