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Reaction of pyrroles with ethyl 2-nitroso- and 2-azo-propenoates, and with ethyl cyanoformate N-oxide: a comparison of the reaction pathways
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Orientador(es)
Resumo(s)
The reaction of ethyl 2-nitrosopropenoate 2a with 1 -methylpyrrole, 2.5-dimethylpyrrole and 2.5-
diphenylpyrrole has been investigated. In every case the products result from highly regioselective attack
at C-2 of the pyrrole by the electrophile. The azopropenoate esters 2b and 2c react similarly with pyrroles,
to the extent that even 1 -(triisopropylsilyl)pyrrole is attacked exclusively at the 2-position by the azo
ester 2b. In contrast, the nitrile oxide ethyl cyanoformate N-oxide 12 reacts at the 3-position of 2.5-
dimethyl- and of 2,5-diphenyl-pyrrole. The reactions of the nitroso and azo esters with pyrroles are
interpreted as Diels-Alder cycloadditions with inverse electron demand.
Descrição
Palavras-chave
Diels-Alder Heterocycles azoalkene
Contexto Educativo
Citação
Journal of the Chemical Society, Perkin Transactions 1, 13, 1391-1391, 1993.