Preparation of tetrahydro-1H-xanthen-1-one and chromen-1-one derivatives via a Morita-Baylis-Hillman/oxa-Michael/elimination cascade

Author(s)

Rodrigues Jr, Manoel T. ; Santos, Hugo ; Zeoly, Lucas A. ; Simoni, Deborah A. ; Moyano, Albert ; Coelho, Fernando

• Document type: Journal article
• Source: ARKIVOC; v. N/A, p. 60-pg., 2020-01-01.

Abstract

The Morita-Baylis-Hillman (MBH) reaction is a carbon-carbon bond forming transformation between an electrophile, typically an aldehyde, and an activated olefin. MBH adducts obtained from 2-hydroxy-benzaldehydes and cyclic enones are potential substrates for the synthesis of xanthenone and chromenone derivatives. In this work, we investigated conditions to obtain tetrahydro-1H-xanthen-1-ones and chromen-1-ones directly via a Morita-Baylis-Hillman/oxa-Michael/elimination cascade catalyzed by a bifunctional, bicyclic imidazolyl alcohol (BIA), which proved to be an effective catalyst for this transformation. The reactions were performed at room temperature in water to give the products in 10-74 % yield. [GRAPHICS] . (AU)

• FAPESP's process: 17/02364-0 - Mechanistic investigations of the biginelli reaction using experimental and theoretical approaches
• Grantee: Rodrigo Antonio Cormanich
• Support Opportunities: Scholarships abroad - Research
• 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
• 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: 15/09205-0 - New frontiers of the Morita-Baylis-Hillman reaction: 1) New applications of a bifunctional catalyst derived from imidazole. 2) Studies on the asymmetric synthesis of a natural high-potency sweetener
• Grantee: Hugo dos Santos
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)