Benzo[b]thiophenes are known to have physiological and biological purposes, such as anti-tumor, anti-fungal, kinases inhibitor, anti-inflammatory, anti-mitotic, and anti-depressants. Substituted benzo[b]thiophenes have also found their application in the area of organic materials as they been used as phosphorescent organic light emitting diodes, organic thin-film field effect transistors, dye-sensitized solar cells and organic dyes and pigments. Herein we report a novel one-pot two step reaction for the synthesis of benzo[b]thiophenes by combing three simple starting reagents. The electrophilic iodocyclization methodology was performed to synthesize benzo[b]thiophene derivatives by using iodine as an electrophile as well as a catalyst for an alkylation reaction which involves 1,3-diketone as a nucleophile. This relatively green and atom economical reaction goes through mild and ambient reaction conditions. Highly functionalized 2,3-disubstituted benzo[b]thiophene core structures were obtained in excellent yields. The reaction also eliminates the excessive use of reagents and did not result in any indicative byproducts.

Synthesis of diverse benzothiophene derivatives via iodine mediated one-pot successive cyclization-alkylation reaction strategy

255th National Meeting (2018)

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