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Synthesis 2021; 53(01): 135-145
DOI: 10.1055/s-0040-1707245
DOI: 10.1055/s-0040-1707245
paper
MeONH2·HCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonyl o-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones
The 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).Weitere Informationen
Publikationsverlauf
Received: 06. Juli 2020
Accepted after revision: 13. Juli 2020
Publikationsdatum:
19. August 2020 (online)
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 compoundsSupporting 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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