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Synthesis 2022; 54(09): 2185-2192
DOI: 10.1055/s-0040-1719880
DOI: 10.1055/s-0040-1719880
paper
Oxidant-Free Selective Synthesis of Functionalized Chroman-4-ones from ortho-Hydroxyacetophenones under HOAc/DMSO Conditions
Authors
Financial support from the National Natural Science Foundation of China (21702002) and the National College Students Innovation and Entrepreneurship Training Program (202110364407) is gratefully acknowledged.
Abstract
A metal-free and oxidant-free acid-promoted DMSO activation and subsequent reaction is reported. In this protocol, two molecules of DMSO are activated by HOAc and serve as dual synthons which react with ortho-hydroxyacetophenones, affording 3-(methylthiomethyl)chroman-4-ones in moderate to good yields with high selectivity.
Key words
ortho-hydroxyacetophenones - chroman-4-ones - dimethyl sulfoxide - dual synthons - benzopyranopyrimidinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719880.
- Supporting Information (PDF)
Publication History
Received: 27 October 2021
Accepted after revision: 13 December 2021
Article published online:
26 January 2022
© 2022. Thieme. All rights reserved
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Selected reviews on the synthesis and biological activities of chroman-4-ones:
For recent examples see the following, and references cited therein:
Recent examples of transition-metal-catalyzed synthesis:
Recent examples of photoredox synthesis:
Recent reviews on DMSO-involved reactions:
Selected examples of protic acid promoted DMSO transformations:
Recent examples of DMSO serving as a dual synthon: