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

Author(s)

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

Affiliation

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

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 85, n. 8, p. 5438-5448, APR 17 2020.
• Web of Science Citations: 1

Abstract

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)

• FAPESP's process: 18/02611-0 - Post-Functionalization of Small Ply-functionalized Molecules: A Robust Approach to the Synthesis of New Structural Patterns with POtential Biological Activity
• Grantee: Fernando Antonio Santos Coelho
• Support Opportunities: Regular Research Grants
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC