Copper(II) Acetate Mediated Synthesis of 3-Sulfonyl-2-aryl-2H-chromenes

Meng-Yang Chang; Yu-Hsin Chen; Han-Yu Chen

doi:10.1055/s-0039-1689973

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3419-3430
DOI: 10.1055/s-0039-1689973

paper

Copper(II) Acetate Mediated Synthesis of 3-Sulfonyl-2-aryl-2H-chromenes

Meng-Yang Chang *

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC

^bDepartment of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan, ROC Email: mychang@kmu.edu.tw

,

Yu-Hsin Chen

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC

,

Han-Yu Chen

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC

› Author Affiliations

Abstract

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Abstract

This paper describes a concise, easy-operation, high-yielding method for the synthesis of 3-sulfonyl-2-aryl-2H-chromenes by a one-pot, straightforward two-step synthetic route, which includes (i) Cu(OAc)₂/PyBOP-mediated intermolecular [4+2] annulation of substituted salicylic acids with β-sulfonylstyrenes in the presence of DMAP in refluxing DMF, and (ii) sequential O-alkylation of the resulting sulfonylflavanones with n-butyl bromide. A plausible mechanism is proposed and discussed. This protocol provides a highly effective annulation via one carbon–oxygen (C–O) and one carbon–carbon (C–C) bond formations.

Key words

copper(II) acetate - 2-aryl-2H-chromenes - salicylic acids - β-sulfonylstyrenes - intermolecular [4+2] annulation

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References

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Supplementary Material