Kirtikumar B. Jadhav - "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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      Chakraborti, Asit K., Rudrawar, Santosh, Jadhav, Kirtikumar B.,   Kaur, Gurmeet, Chankeshwara, Sunay V. Green Chemistry  2007 9 (12) 1335-1340

      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 [degree]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 [small alpha],[small   beta]-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.

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