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Orientador(es)
Resumo(s)
Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone–phenol rearrangement to provide the corresponding quinolone–phenol in high yield.
Descrição
Palavras-chave
Intramolecular Acyldiazenecarboxylates Synthesis Heterocycles
Contexto Educativo
Citação
PRATA, José V.; [et al] – Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles. Journal of the Chemical Society, Perkin Transactions 1. ISSN 1470-4358. N.º 4 (2002), pp. 513-528
Editora
Royal Society of Chemistry