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

Chakraborti, Asit K. ; Rudrawar, Santosh ; Jadhav, Kirtikumar B. ; Kaur, Gurmeet ; Chankeshwara, Sunay V. (2007) “On water” organic synthesis: a highly efficient and clean synthesis of 2-aryl/heteroaryl/styryl benzothiazoles and 2-alkyl/aryl alkyl benzothiazolines Green Chemistry, 9 (12). pp. 1335-1340. ISSN 1463-9262

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2007...

Related URL: http://dx.doi.org/10.1039/B710414F

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.

Item Type:Article
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ID Code:100415
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