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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Rodrigues Jr, Manoel T. ; Santos, Hugo [1] ; Zeoly, Lucas A. [1] ; Simoni, Deborah A. [2] ; Moyano, Albert [3] ; Coelho, Fernando [1]
Total Authors: 6
Affiliation:
[1] Rodrigues Jr, Jr., Manoel T., Univ Estadual Campinas, UNICAMP, Inst Chem, Lab Synth Nat Prod & Drugs, POB 6154, BR-13083970 Campinas, SP - Brazil
[2] Univ Estadual Campinas, UNICAMP, Inst Chem, Lab Crystallog, POB 6154, BR-13083970 Campinas, SP - Brazil
[3] Univ Barcelona, Fac Quim, Dept Quim Inorgan & Organ, Seccio Quim Organ, Marti i Franques 1-11, Barcelona 08028, Catalonia - Spain
Total Affiliations: 3
Document type: Journal article
Source: ARKIVOC; n. 2, p. 77+, 2020.
Web of Science Citations: 0
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: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
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 type: Scholarships in Brazil - Doctorate (Direct)
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 type: 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 type: Scholarships abroad - Research