Room temperature dithiocarbamation of 2-tetralones with elemental sulfur and isothiocyanates S8/R-NCS: atom-efficient access to 4-hydroxythiazolidine-2-thiones

Le Anh Nguyen; Quoc Anh Ngo; Pascal Retailleau; Thanh Binh Nguyen

doi:10.1039/d4cc05053c

Room temperature dithiocarbamation of 2-tetralones with elemental sulfur and isothiocyanates S₈/R-NCS: atom-efficient access to 4-hydroxythiazolidine-2-thiones

Chem Commun (Camb). 2024 Nov 14;60(92):13586-13589. doi: 10.1039/d4cc05053c.

Authors

Le Anh Nguyen^{1

2}, Quoc Anh Ngo¹, Pascal Retailleau³, Thanh Binh Nguyen³

Affiliations

¹ Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam. ngoqanh@ich.vast.vn.
² Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
³ Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av de la Terrasse, 91198 Gif-sur-Yvette, France. thanh-binh.nguyen@cnrs.fr.

PMID: 39480192
DOI: 10.1039/d4cc05053c

Abstract

2-Tetralones were found to undergo dithiocarbamation with elemental sulfur and isothiocyanates S₈/R-NCS in the presence of N-methylpiperidine as a base catalyst under solvent-free conditions. The reaction could proceed quickly at room temperature to provide convenient access to substituted 4-hydroxythiazolidine-2-thiones with complete atom efficiency. The adducts could be easily dehydrated in neat TFA to give thiazole-2-thiones.