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Issue 12, 2007
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“On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines

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Abstract

A convenient and clean “on water”-mediated synthesis of benzothiazoles/benzothiazolines is reported. Aromatic, heteroaromatic, and styryl aldehydes are converted to 2-substituted benzothiazoles in high yields in a one-pot reaction with 2-aminothiophenol in water at 110 °C (oil-bath). Alkyl and aryl alkyl aldehydes afforded the benzothiazolines. The reaction is highly chemoselective with no competitive thia-Michael addition, O-dealkylation/debenzoylation, reduction of the nitro or the α,β-unsaturated carbonyl groups, and substitution of the halogen atom or the nitro group. The reaction is found to be general with respect to the 2-aminothiophenol substrate through the reaction of a few substituted 2-aminothiophenols with a few representative aromatic and aliphatic aldehydes. The procedure does not involve the use of any additional reagent/catalyst, produces no waste, and represents a green synthetic protocol.

Graphical abstract: “On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines

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Article information


Submitted
09 Jul 2007
Accepted
17 Sep 2007
First published
10 Oct 2007

Green Chem., 2007,9, 1335-1340
Article type
Paper

“On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines

A. K. Chakraborti, S. Rudrawar, K. B. Jadhav, G. Kaur and S. V. Chankeshwara, Green Chem., 2007, 9, 1335
DOI: 10.1039/B710414F

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