A General Protocol for the Aqueous Morita-Baylis-Hillman Reaction between Cyclic Enones and 1,2-Dicarbonyl Compounds

Author(s)

Rodrigues Jr, Manoel T. ; Serafim, Jose Claudio ; Santos, Hugo ; Arantes, Joao ; Senna, Ana Julia ; Acconcia, Lais V. ; Moyano, Albert ; Coelho, Fernando

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 27, n. 48, p. 9-pg., 2024-12-11.

Abstract

In this report, we present an extensive methodological study of the aqueous Morita-Baylis-Hillman (MBH) reaction of a range of cycloenones with di- and tricarbonyl compounds, such as glyoxal derivatives, aliphatic and aromatic alpha-keto esters, 1,2-diketones, diethyl ketomalonate, ninhydrin, acenaphthenequinone, and phenanthrene-9,10-dione, through mediation of a bicyclic imidazolyl alcohol (BIA) as catalyst in aqueous medium. The desired MBH adducts were obtained in up to 98 % yield. The synthetic applicability of the MBH adducts was demonstrated by the preparation of an acenaphtho[1,2-b]indole derivative. (AU)

• 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: 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: 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)
• FAPESP's process: 23/18007-3 - Strategies for the Synthesis of Structurally Complex Heterocycles and Evaluation of Potential Biological Activities
• Grantee: Fernando Antonio Santos Coelho
• Support Opportunities: Regular Research Grants