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Isatin as 2-Aminobenzaldehyde Surrogate: Transition Metal-free Efficient Synthesis of 2-(2’-Aminophenyl)benzothiazole Derivatives

Abstract

A transition metal-free, convenient, and efficient practical approach has been devised for the synthesis of substituted 2-(2’-aminophenyl)benzothiazoles via sulfur insertion strategy using isatin derivatives as 2-aminobenzaldehyde surrogates. KI assisted one-pot operation of isatin, arylamines and elemental sulfur resulted in formation of a C-N and two C-S bonds and cascade cleavage of isatin ring resulting in formation of 2-(2’-aminophenyl)benzothiazoles. The significant features of this strategy are the readily available and inexpensive starting materials, broad substrate scope, sustainable reaction conditions and high yield of products. Importantly, the strategy was found appropriate for gram scale synthesis (> 10g) of 2-(2’-aminophenyl)benzothiazole derivatives. Moreover, the excellent photophysical properties (ΦF up to 60%) of 2-(2’-aminophenyl)benzothiazole derivatives provide huge scope in material science.

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Supplementary files

Article information


Submitted
29 Apr 2020
Accepted
19 May 2020
First published
20 May 2020

Org. Biomol. Chem., 2020, Accepted Manuscript
Article type
Paper

Isatin as 2-Aminobenzaldehyde Surrogate: Transition Metal-free Efficient Synthesis of 2-(2’-Aminophenyl)benzothiazole Derivatives

M. Singh, V. -, A. K. Paul and V. Singh, Org. Biomol. Chem., 2020, Accepted Manuscript , DOI: 10.1039/D0OB00888E

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