Palladium-Mediated Oxidative Annulation of delta-Indolyl-alpha,beta-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines

Autor(es)

Agy, Andre Capretz ^[1] ; Rodrigues, Jr., Manoel T. ^[1] ; Zeoly, Lucas A. ^[1] ; Simoni, Deborah A. ^[2] ; Coelho, Fernando ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Lab Synth Nat Prod & Drugs, POB 6154, BR-13083979 Campinas, SP - Brazil

^[2] Univ Estadual Campinas, Lab Crystallog, Inst Chem, POB 6154, BR-13083979 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 84, n. 9, p. 5564-5581, MAY 3 2019.
• Citações Web of Science: 4

Resumo

The cyclopenta{[}b]indole moiety represents a key skeletal unit in several natural and synthetic compounds that exhibit diverse biological properties. We described herein a two-step sequence for synthesizing cyclopenta{[}b]indoles with great structural diversity in overall yields up to 37%. The key step was a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara-Moritani reaction). The obtained cyclopenta{[}b]indoles were used as substrates in heterogeneous hydrogenation reactions to afford new fused indolines in moderate yields. An acid-catalyzed intramolecular cyclization of three such indolines gave tetracyclic lactams in 89, 90, and 61% yields. (AU)

• Processo FAPESP: 13/10449-5 - Adutos de Morita-Baylis-Hillman como blocos de contrução eficientes para a síntese de moléculas de interesse biológico
• 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