Issue 15, 2025

One-pot synthesis of diaroyl benzothiepine-1,1-dioxides

Abstract

We report the one-pot two-step synthesis of diaroyl benzothiepine-1,1-dioxides via rongalite-mediated double sulfination of α-bromoacetophenones followed by double condensation of the resulting 1,3-diaroyl sulfones and o-phthalaldehydes. In the (1C + 1C + 1S + 4C) reaction process, a seven-membered ring system could be constructed by two carbon–sulfur (C–S) single bonds and two carbon–carbon double bonds (C[double bond, length as m-dash]C) under mild conditions. A related putative mechanism is proposed and discussed in this article.

Graphical abstract: One-pot synthesis of diaroyl benzothiepine-1,1-dioxides

Supplementary files

Article information

Article type
Paper
Submitted
04 Feb 2025
Accepted
10 Mar 2025
First published
11 Mar 2025

Org. Biomol. Chem., 2025,23, 3572-3582

One-pot synthesis of diaroyl benzothiepine-1,1-dioxides

M. Chang and N. Hsueh, Org. Biomol. Chem., 2025, 23, 3572 DOI: 10.1039/D5OB00198F

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