Synlett 2020; 31(06): 622-626
DOI: 10.1055/s-0039-1691497
cluster
© Georg Thieme Verlag Stuttgart · New York

Aza-Morita–Baylis–Hillman Reaction with Vinyl-oxadiazoles: An Expeditious Approach to Access New Heterocyclic Arrangements

André Capretz-Agy
,
Fábio S. Fernandes∗
,
Manoel T. Rodrigues Jr.
,
Caroline Conti
,
Fernando Coelho  ∗
São Paulo Foundation for Science (FAPESP, Grant No. 2013/07600-3, 2018/02611-0, and 2016/23005-6 to F.C and F.S.F.), Coordenacão de Aperfeiçoamento de Pessoal de Nivel Superior–Brasil (CAPES, Finance Code 001 to M.T.R.Jr. and A.A.C), and Brazilian National Council for Science and Development (CNPq, Processes No. 422890/2016-2 and 301330/2018-2).
Further Information

Publication History

Received: 16 October 2019

Accepted after revision: 09 November 2019

Publication Date:
25 November 2019 (online)

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Published as part of the ISySyCat2019 Special Issue

Abstract

In this communication, we disclosed a new aza-MBH reaction in which traditional nucleophilic partners of these reactions (e.g., acrylates, nitroolefins or enones) were replaced by vinyl-1,2,4-oxadiazoles. Thus, the aza-MBH reaction between 5-aryl-3-vinyl-1,2,4-oxadiazoles and N-sulfonylimines, catalyzed by the mixture DABCO/AcOH, provides a class of new adduct in yields varying from 31% up to 93% in reaction times from 30 minutes to 24 hours. Due to the biological activities and technological applications associated with the 1,2,4-oxadiazole motifs, this new class of heterocycles offers great synthetic and commercial potentiality.

Key words

vinyl-oxadiazoles - heterocycles - organocatalysis - Morita–Baylis–Hillman reaction - aza-Morita–Baylis–Hillman - nucleophilic partner

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691497.
  • Supporting Information
 

  • References and Notes

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