Herein, we report two methodologies for the synthesis of 2,3-disubstituted benzo[b]thiophenes. In the first methodology we report a one-pot cyclization-alkylation reaction where iodine acts as a cyclizing agent as well as a catalyst. Iodine mediated cyclization of various propargyl alcohols resulted in the formation of benzo[b]thiophen-2-ylmethanol, which undergoes iodine catalyzed alkylation reaction using various 1,3-dicarbonyl molecules. In the second one-pot methodology we report another iodine mediated cyclization reaction in combination with an alcohol oxidation reaction. In this cyclization-oxidation methodology benzo[b]thiophene obtained from an iodocyclization reaction of alkynyl thioether is further reacted with potassium carbonate and iodine to give an aldehyde or a ketone moiety. Both methodologies employ mild conditions and results in high yield of desired functionalized benzo[b]thiophenes. Sulfur heterocycles are well established in the field of material science and pharmaceuticals. The properties of benzo[b]thiophenes have been showed case in phosphorescent organic light-emitting diodes and dye-sensitized solar cells due to thermal stability and electronic properties. Benzo[b]thiophenes are also well-known for their range of biological activities They are known to exhibit antiviral, antimalarial, anti-inflammatory, anti-tumor, anti-mitotic activities. Benzo[b]thiophene core structures are also well established as estrogen receptor modulator and kinases inhibitor.

Iodine mediated one-pot cyclization-alkylation and cyclization-oxidation methodologies for the synthesis of 2,3-disubstituted benzo[b]thiophenes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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