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Amine‐carbon disulfide promoted synthesis of novel benzo[ e ][1,3]thiazepin‐5(1 H )‐one derivatives
Author(s) -
Asgari Mohammad Sadegh,
Bahadorikhalili Saeed,
Asadi Mehdi,
Rashidi Ranjbar Parviz,
Larijani Bagher,
Rahimi Rahmatollah,
Mahdavi Mohammad
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3794
Subject(s) - chemistry , carbon disulfide , amine gas treating , sulfuric acid , dimethylformamide , disulfide bond , ethanol , organic chemistry , carbon chain , aldehyde , salt (chemistry) , carbon fibers , medicinal chemistry , solvent , catalysis , biochemistry , materials science , composite number , composite material
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(1 H )‐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(1 H )‐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.