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Synlett 2025; 36(11): 1548-1552
DOI: 10.1055/s-0043-1773524
DOI: 10.1055/s-0043-1773524
letter
Ring-Opening Reactions of Donor–Acceptor Cyclopropanes with Some Enolizable Azaheterocyclic Thiones: S- versus N-Attack
This work was in part supported by the University of Lodz within the IDUB-Grant (to G.M.). M.K. thanks the Bio-Med-Chem Doctoral School of the Uniwersytet Łódzki and Łodź Institutes of the Polish Academy of Sciences for a stipend.
This work is dedicated to Professor Mieczysław Mąkosza (Warsaw) on the occasion of his 90th birthday
Abstract
We report ring-opening reactions of donor–acceptor (D–A) cyclopropanes with a variety of five- and six-membered enolizable azaheterocyclic thiones, using Sc(OTf)3 as catalyst in dichloromethane. The majority of these systems reacted through nucleophilic S-attack at the donor position of the cyclopropane. 5-Mercapto-1,3,4-triazoles were shown to give the products of formal N-attack, and systems bearing two external C-S bonds could react with two equivalents of D–A cyclopropane to generate difunctionalized azaheterocycles.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055s-0043-1773524.
- Supporting Information
Publication History
Received: 24 November 2024
Accepted after revision: 04 February 2025
Article published online:
20 March 2025
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