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Synlett
DOI: 10.1055/a-2746-2320
DOI: 10.1055/a-2746-2320
Letter
Published as part of the Special Issue dedicated to Prof. S. Chandrasekaran on his
80th birthday
Transition-Metal Free Chemoselective C(sp3)–S Cross-Coupling/Cyclization Cascade: Reagent-Controlled Divergent Synthesis of Methylene-functionalized Thiazolidines and 1,3-Thiazinanes
Authors
Supported by: Anusandhan National Research Foundation CRG/2023/000021
Supported by: IoE 6031
Funding Information We gratefully acknowledge the financial support from the IoE, BHU Incentive Grant (Scheme No. 6031), Anusandhan National Research Foundation (CRG/2023/000021) and JC Bose National Fellowship (JCB/2020/000023), New Delhi.
Abstract
A highly chemoselective consecutive cross-coupling/cyclization cascade of β-ketothioamides with dihaloalkanes has been achieved under transition-metal free condition, enabling the formation of methylene-functionalized thiazolidines and 1,3-thiazinanes at room temperature in open air in high yields. The typical features of this straightforward sustainable approach include readily accessible starting materials, simple one-pot operation, atom-/step-economy, cost-effective, good substrate scope, and scalability. Noteworthy, HX is the only by-product, and stereochemistry of the exocyclic methylene moiety was assigned to have Z-configuration. Late-stage functionalization could provide new opportunities for the discovery of N, S-heterocyclic drugs, and other potential functional molecules.
Publication History
Received: 30 September 2025
Accepted after revision: 12 November 2025
Accepted Manuscript online:
12 November 2025
Article published online:
04 December 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
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