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Synthesis 2021; 53(01): 135-145
DOI: 10.1055/s-0040-1707245
paper
© Georg Thieme Verlag Stuttgart · New York

MeONH2·HCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonyl o-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones

Meng-Yang Chang  ∗
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Email: mychang@kmu.edu.tw
b   Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan
,
Kuan-Ting Chen
a   Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan   Email: mychang@kmu.edu.tw
› Author AffiliationsThe authors would like to thank the Ministry of Science and Technology of the Republic of China, Taiwan for financial support (MOST 109-2113-M-037-014-MY3).
Further Information

Publication History

Received: 06 July 2020

Accepted after revision: 13 July 2020

Publication Date:
19 August 2020 (online)

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Abstract

A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o-hydroxyacetophenones with methyl sulfoxides via a MeONH2·HCl-mediated sequential methylenation/ conjugate­ addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.

Key words

chroman-4-ones - o-hydroxyacetophenones - methylenation - methyl sulfoxides - sulfonyl compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707245. Included are scanned photocopies of NMR spectra for all compounds and X-ray analysis data of 4a, 4f, 4x, 5a and 5b.
  • Supporting Information
  • CIF File
 

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