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Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives Publisher



Asgari MS1 ; Bahadorikhalili S1 ; Asadi M2 ; Rashidi Ranjbar P1 ; Larijani B3 ; Rahimi R4 ; Mahdavi M3
Authors

Source: Journal of Heterocyclic Chemistry Published:2020


Abstract

In this paper, a simple method is introduced for the synthesis of novel 4-substituted-3-thioxo-3,4-dihydrobenzo[e][1,3]thiazepin-5(1H)-one derivatives. The synthesis is based on a two-step reaction of 2-methylbenzoic acid, an amine, and carbon disulfide. In the first step, 2-methylbenzoic acid reacts with sulfuric acid in ethanol, followed by the reaction with N-bromosuccinimide to produce ethyl 2-(bromomethyl)benzoate. Amine and carbon disulfide react in a separate flask in basic medium to give carbamodithioate salt. Carbamodithioate and ethyl 2-(bromomethyl)benzoate react together in dimethylformamide to produce the desired 4-substituted-3-thioxo-3,4-dihydrobenzo[e][1,3]thiazepin-5(1H)-one derivatives. The method is simple and fast and is applicable to a wide variety of substrates and gives the desired products in high isolated yields. © 2019 Wiley Periodicals, Inc.
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