An efficient synthetic route to biologically relevant 2-phenylbenzothiazoles substituted on the benzothiazole ring

Weekes, Ashley Ann, Bagley, Mark Christopher and Westwell, Andrew D. ORCID: https://orcid.org/0000-0002-5166-9236 2011. An efficient synthetic route to biologically relevant 2-phenylbenzothiazoles substituted on the benzothiazole ring. Tetrahedron 67 (40) , pp. 7743-7747. 10.1016/j.tet.2011.08.004

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Abstract

Certain 2-phenylbenzothiazoles containing substituents on the benzothiazole ring possess important biological properties, yet the majority of synthetic methods to 2-phenylbenzothiazoles described to date focus on their unsubstituted ring counterparts. Here we describe a new concise and efficient synthetic route to biologically relevant 2-phenylbenzothiazoles in high yield from the reaction of substituted 2-aminothiophenol disulfides and benzaldehydes, promoted by the inexpensive and non-toxic inorganic oxidant sodium metabisulfite in DMSO at 120 °C. Our new method is tolerant of a range of substituents on both the benzothiazole and phenyl ring, and affords efficient access to substituted 2-phenylbenzothiazoles without the need for column chromatography.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry Pharmacy
Subjects:	Q Science > QD Chemistry R Medicine > RM Therapeutics. Pharmacology
Uncontrolled Keywords:	2-Phenylbenzothiazoles ; Sodium metabisulfite; enzaldehydes ; Aromatic heterocycle synthesis
Publisher:	Elsevier
ISSN:	0040-4020
Last Modified:	18 Oct 2022 14:01
URI:	https://orca.cardiff.ac.uk/id/eprint/16203

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