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

Title: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

Volume: 12 Issue: 6

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

Affiliation:

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

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.

Cite this article as:

Rezki Nadjet, Aouad Reda Mohamed, Messali Mouslim and El Ashry Sayed H. El, 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, Letters in Organic Chemistry 2015; 12 (6) . https://dx.doi.org/10.2174/1570178612666150331204431