Alkylation of 5-(3-chlorobenzo[b]thien-2-yl)-1,2,4-triazole-3-thione with Epichlorhydrin and the Role of MW and Solid Support in the Reaction

Author(s): Nadjet Rezki, Mohamed Reda Aouad, Mouslim Messali, El Sayed H. El Ashry

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 6 , 2015

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Graphical Abstract:


An efficient eco-friendly approach has been adopted for the selective synthesis of 2,3- epoxypropylsulfanyltriazole 4 from the reaction of 1-chloro-2,3-epoxy-propane (2) with 5-(3- chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole-3-thione (1) under solvent free microwave conditions in the presence of a solid support. Instead, when the mixture of reactants was irradiated for prolonged time in the absence of solid support, triazolo[ 2,1-b]thiazine 3 was exclusively afforded in excellent yield. On the other hand, performing the irradiation in the presence of a base, mixtures of compounds 4 and 3 were obtained; the ratio of the two products was dependent on the nature of the base, although 4 was the major product in each case.

Keywords: Benzo[b]thiophene, 1, 2, 4-triazoles, thiazine, triazolothiazine, solid support, microwave, green chemistry, epoxide ring opening.

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Article Details

Year: 2015
Published on: 03 June, 2015
Page: [418 - 423]
Pages: 6
DOI: 10.2174/1570178612666150331204431
Price: $65

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