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

Weekes, Ashley Ann, Bagley, Mark Christopher and Westwell, Andrew D. 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: 04 Jun 2017 03:04
URI: http://orca.cf.ac.uk/id/eprint/16203

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