Effective and Catalyst-Free Preparation of Thiazolidines via Novel [3+2] Annulation of 1,4-Dithiane-2,5-diol and Benzothiazolimines

Abstract

A novel [3+2] annulation of 1,4-dithiane-2,5-diol and benzothiazolimines has been developed for the efficient, one-step preparation of highly sterically demanding thiazolidines in excellent yields (up to 99%) and moderate diastereoselectivities (1:1 to 2.4:1) under mild conditions within a few minutes. A series of thiazolidines compounds were obtained and a scaled-up experiment was conducted with excellent results. The absorption, metabolism, and toxic (ADMET) properties of the compounds were evaluated with good results, demonstrating the potential applications of this protocol.

Key words

[3+2] annulation - 1,4-dithiane-2,5-diol - benzothiazolimines - thiazolidines - ADMET

Publication History

Received: 31 October 2024

Accepted after revision: 02 January 2025

Accepted Manuscript online:
02 January 2025

Article published online:
31 January 2025

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• 11 CCDC 2306452 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures