Redox condensation of o-halonitrobenzenes, sulfur and isothiocyanates: access to 2-aminobenzothiazoles

Le Anh Nguyen; Dinh Hung Mac; Pascal Retailleau; Thanh Binh Nguyen

doi:10.1039/d4ob01512f

Redox condensation of o-halonitrobenzenes, sulfur and isothiocyanates: access to 2-aminobenzothiazoles

Org Biomol Chem. 2024 Nov 6;22(43):8586-8590. doi: 10.1039/d4ob01512f.

Authors

Le Anh Nguyen^{1

2}, Dinh Hung Mac³, Pascal Retailleau⁴, Thanh Binh Nguyen⁴

Affiliations

¹ Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
² Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
³ Faculty of Chemistry, VNU University of Science, Vietnam National University in Hanoi, 19 Le Thanh Tong, Hanoi, Vietnam. macdinhhung@hus.edu.vn.
⁴ 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: 39373946
DOI: 10.1039/d4ob01512f

Abstract

The elemental sulfur and isothiocyanate (S₈/RNCS) couple was found to undergo redox condensation with o-halonitrobenzenes in the presence of N-methylpiperidine as a base in N-methylpyrrolidin-2-one to provide step- and redox-economical access to 2-aminobenzothiazoles. Alternatively, dithiocarbamate salts generated in situ from addition of amines and CS₂ could be used in place of the S₈/RNCS couple.