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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.)

Vinyl-1,2,4-oxadiazoles Behave as Nucleophilic Partners in Morita-Baylis-Hillman Reactions

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Author(s):
Fernandes, Fabio S. [1] ; Rodrigues, Jr., Manoel T. [1] ; Zeoly, Lucas A. [1] ; Conti, Caroline [1] ; Angolini, Celio F. F. [2] ; Eberlin, Marcos Nogueira [2, 3] ; Coelho, Fernando [1]
Total Authors: 7
Affiliation:
[1] Univ Estadual Campinas, Lab Sintese Prod Nat & Frmacos, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil
[2] Univ Estadual Campinas, Lab ThoMSon Espectrometria Massas, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil
[3] Mackenzie Presbiterian Univ, BR-01302907 Sao Paulo - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Journal of Organic Chemistry; v. 83, n. 24, p. 15118-15127, DEC 21 2018.
Web of Science Citations: 5
Abstract

We describe that vinyl-oxadiazoles function as a new and efficient nucleophilic partner for the Morita-Baylis-Hillman (MBH) reaction. The reaction between 5-vinyl-3-aryl-1,2,4-oxadiazoles and aromatic and aliphatic aldehydes, catalyzed by DABCO in the absence of solvent, showed high efficiency to afford a new class of heterocyclic MBH adducts with potential biological activity on yields up to 99% and short reaction times. These synthetically attractive adducts bear a heterocyclic scaffold of large pharmaceutical and commercial interest associated with a plethora of biological effects and technological applications. We also demonstrate their synthetic usefulness by a photoinduced addition reaction to a polyfunctionalized amino alcohol. (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
FAPESP's process: 16/23005-6 - Synthesis of new heterocycles exhibiting potential biological activities by exploring the Morita-Baylis-Hillman adducts as building blocks
Grantee:Fábio de Souza Fernandes
Support Opportunities: Scholarships in Brazil - Post-Doctoral