Tetrahedron Letters

Thiocyanation of alkylanilines. A simple and efficient synthesis of thiosulfonates containing 2-aminobenzothiazole

JVNV Prasad, A Panapoulous, JR Rubin

Index: Vara Prasad; Panapoulous; Rubin, John R. Tetrahedron Letters, 2000 , vol. 41, # 21 p. 4065 - 4068

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Citation Number: 24

Abstract

Thiocyanation of anilines was used to introduce a thiol functionality and to construct the aminothiazole ring, all in a single step. A systematic study of thiocyanation of alkyl anilines was investigated to understand the regiochemistry of the reaction. X-Ray crystal structures of two 2-aminobenzothiazoles were determined to assign the structures without any ambiguity. The intermediates obtained were further expanded to thiosulfonates containing 2- ...