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Issue 17, 2020
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Synthesis of methylene cyclopropane-fused chromenes and dihydroquinolines by sequential [4 + 2]- and [1 + 2]-annulation

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Abstract

A base promoted sequential [4 + 2]- and [1 + 2]-annulation of 2-hydroxychalcones or 2-tosylaminochalcones with prop-2-ynylsulfonium salts has been developed to give the corresponding methylene cyclopropane fused dihydroquinolines or chromenes in moderate to good yields. This transformation has advantage of wide substrate scope and functional group tolerance as well as excellent regioselectivity. Prop-2-ynylsulfonium salts act as both C2 and C1 synthons in the tandem processes.

Graphical abstract: Synthesis of methylene cyclopropane-fused chromenes and dihydroquinolines by sequential [4 + 2]- and [1 + 2]-annulation

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Supplementary files

Article information


Submitted
22 Feb 2020
Accepted
07 Apr 2020
First published
07 Apr 2020

Org. Biomol. Chem., 2020,18, 3303-3311
Article type
Paper

Synthesis of methylene cyclopropane-fused chromenes and dihydroquinolines by sequential [4 + 2]- and [1 + 2]-annulation

T. Lu, X. Zhang and Z. Miao, Org. Biomol. Chem., 2020, 18, 3303
DOI: 10.1039/D0OB00389A

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