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

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

Show Affiliations

1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
2. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
3. Department of Medicinal chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medicinal Sciences, Tehran, Iran
4. Department of Chemistry, Iran University of Science and Technology, Tehran, Iran

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.

Style	Citing Format
MLA	Asgari MS, et al.. "Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives." Journal of Heterocyclic Chemistry, vol. 57, no. 1, 2020, pp. 413-418.
APA	Asgari MS, Bahadorikhalili S, Asadi M, Rashidi Ranjbar P, Larijani B, Rahimi R, Mahdavi M (2020). Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives. Journal of Heterocyclic Chemistry, 57(1), 413-418.
Chicago	Asgari MS, Bahadorikhalili S, Asadi M, Rashidi Ranjbar P, Larijani B, Rahimi R, Mahdavi M. "Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives." Journal of Heterocyclic Chemistry 57, no. 1 (2020): 413-418.
Harvard	Asgari MS et al. (2020) 'Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives', Journal of Heterocyclic Chemistry, 57(1), pp. 413-418.
Vancouver	Asgari MS, Bahadorikhalili S, Asadi M, Rashidi Ranjbar P, Larijani B, Rahimi R, et al.. Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives. Journal of Heterocyclic Chemistry. 2020;57(1):413-418.
BibTex	@article{ author = {Asgari MS and Bahadorikhalili S and Asadi M and Rashidi Ranjbar P and Larijani B and Rahimi R and Mahdavi M}, title = {Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives}, journal = {Journal of Heterocyclic Chemistry}, volume = {57}, number = {1}, pages = {413-418}, year = {2020} }
RIS	TY - JOUR AU - Asgari MS AU - Bahadorikhalili S AU - Asadi M AU - Rashidi Ranjbar P AU - Larijani B AU - Rahimi R AU - Mahdavi M TI - Amine-Carbon Disulfide Promoted Synthesis of Novel Benzo[E][1,3]Thiazepin-5(1H)-One Derivatives JO - Journal of Heterocyclic Chemistry VL - 57 IS - 1 SP - 413 EP - 418 PY - 2020 ER -

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