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Paper | Regular issue | Vol 26, No. 2, 1987, pp.427-436
Published online, 1st January, 1970
DOI: 10.3987/R-1987-02-0427
Ortho-lithiation of 2-(Benzothiazol-2-ylthio)pyridine. Preparation of 2,3-Disubstituted Pyridines

Alan R. Katritzky,* Jose M. Ayrrecoechea, and Luis M. Vazquez de Miguel

*Center for Drug Discovery, College of Pharmacy, University of Florida, Gainesville, Florida 32611-7200, U.S.A.

Abstract

2-(Benzothiazal-2-ylthio)py1idine undergoes lithiation exclusively at the 3-position. The products of reaction with electrophiles of the lithiated species undergo sulfide cleavage to give 3-substituted 2-alkylthiopyridines and/or 3-substituted pyridine-2-thiones.