Some nucleophilic reactions of 2-isothiocyanatobenzyl bromide. A new simple synthesis of 2-substituted 4H-benzo [d][1, 3] thiazines

J Gonda, P Kristian

Index: Gonda, Jozef; Kristian, Pavol Collection of Czechoslovak Chemical Communications, 1986 , vol. 51, # 12 p. 2802 - 2809

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Citation Number: 17

Abstract

Abstract N-Bromosuccinimide reacts with o-tolyl isothiocyanate to afford 2- isothiocyanatobenzyl bromide, a new type of bifunctional synthon. Nucleophiles I-, SCN-, 4- CH 3 C 6 H 4 SO 2-and hexamethylenetetramine yield substitution products of bromine. Amines and phenols react exclusively with the NCS grouping under formation of unstable thioureas, which in turn cyclize to the corresponding 4H-benzo [d][1, 3] thiazines. Structure ...