One pot synthesis of 2‐substituted thiobenzoazoles containing α‐sulfenylated aromatic ketones under transition metal‐free conditions

An efficient synthesis of 2‐substituted thiobenzoazoles in pot manner was reported. Thus, tetramethylthiuram disulfide (TMTD) reacted with 2‐aminothiophenol, 2‐aminophenol, or 1,2‐phenylenediamine to form 2‐mercaptobenzo heterocycles through cyclization, and the subsequent C‐S bonding with 2‐bromoac...

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Published in:Journal of heterocyclic chemistry 2023-10, Vol.60 (10), p.1793-1798
Main Authors: Cheng, Xi, Xu, Xiao‐Hu, Dong, Zhi‐Bing
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Language:English
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Aminophenol
Ketones
Phenylenediamine
Substitutes
Synthesis
Transition metals
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Dong, Zhi‐Bing
description An efficient synthesis of 2‐substituted thiobenzoazoles in pot manner was reported. Thus, tetramethylthiuram disulfide (TMTD) reacted with 2‐aminothiophenol, 2‐aminophenol, or 1,2‐phenylenediamine to form 2‐mercaptobenzo heterocycles through cyclization, and the subsequent C‐S bonding with 2‐bromoacetophenones gave the desired 2‐substituted thiobenzoazoles containing α ‐sulfenylated aromatic ketones smoothly. The method features transition metal‐free, simple operation, mild conditions, short reaction time, and good yields, showing potential synthetic value for the synthesis of a variety of biological or pharmaceutically active compounds.
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subjects Aminophenol
Ketones
Phenylenediamine
Substitutes
Synthesis
Transition metals
title One pot synthesis of 2‐substituted thiobenzoazoles containing α‐sulfenylated aromatic ketones under transition metal‐free conditions
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