Catalyst-Free Conjugate Addition of Indolizines to In Situ-Generated Oxidized Morita-Baylis-Hillman Adducts

Autor(es)

Silva, Thiago S. ^[1] ; Zeoly, Lucas A. ^[1] ; Coelho, Fernando ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, Lab Synth Nat Prod & Drugs, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 85, n. 8, p. 5438-5448, APR 17 2020.
• Citações Web of Science: 1

Resumo

Sequential one-pot 2-iodoxybenzoic acid (IBX) oxidation of Morita-Baylis-Hillman (MBH) adducts followed by catalyst-free indolizine conjugate addition was developed. The wide scopes of MBH adducts and indolizines were investigated, and densely functionalized adducts were obtained in yields of up to 94%. The conjugate addition step occurred in less than a minute at room temperature with total regioselectivity toward indolizine C3 carbon. Less nucleophilic C1 carbon was also alkylated when C3-substituted indolizines were employed as the substrate. (AU)

• Processo FAPESP: 18/02611-0 - A pós-Funcionalização de Pequenas Moléculas Poli-funcionalizadas: Uma Abordagem Robusta para a Síntese de Novos Padrões Estruturais com Potencial Atividade Biológica
• Beneficiário: Fernando Antonio Santos Coelho
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs