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Synthesis of 3-iodobenzo[b]thiophenes via iodocyclization/etherification reaction sequence
Journal article   Peer reviewed

Synthesis of 3-iodobenzo[b]thiophenes via iodocyclization/etherification reaction sequence

Tanay Kesharwani, Jason Craig, Cathlene Del Rosario, Renee Shavnore and Cory Komman
Tetrahedron letters, Vol.55(50), pp.6812-6816
12/10/2014
DOI: https://doi.org/10.1016/j.tetlet.2014.10.064
Web of Science ID: WOS:000345809800014

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Abstract

An efficient method was developed for the synthesis of benzo[b]thiophene core structure using a two-step, multicomponent reaction resulting in favorable yields. This convergent reaction requires room temperature thus eliminating the harsh reaction conditions usually associated with the synthesis of benzo[b]thiophene ring structures. Used in many drugs that treat conditions such as osteoporosis, asthma, and fungal infections, the benzo[b]thiophene core structure is of extreme importance to medicinal and pharmaceutical research. The key step in this process involves the use of an iodine as a cyclizing agent that acts simultaneously as a catalyst. Alcohols such as alkyl, allyl, propargyl, and benzylic are employed to prepare a diverse library of 3-iodobenzo[b]thiophenes. (C) 2014 Elsevier Ltd. All rights reserved.

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