Synlett 2017; 28(09): 1051-1056
DOI: 10.1055/s-0036-1588415
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© Georg Thieme Verlag Stuttgart · New York

Tandem Oxidative Phenol Dearomatization/Formal [3+2] Annulation Protocol En Route to Highly Functionalized Benzothiophenes

Santhosh Kumar Chittimalla*
Medicinal Chemistry Department, AMRI Singapore Research Centre, 61 Science Park Road, #05-01, The Galen, Science Park II, Singapore 117525, Singapore   Email: santhosh.chittimalla@amriglobal.com   Email: chemcsk@gmail.com
,
Chennakesavulu Bandi
Medicinal Chemistry Department, AMRI Singapore Research Centre, 61 Science Park Road, #05-01, The Galen, Science Park II, Singapore 117525, Singapore   Email: santhosh.chittimalla@amriglobal.com   Email: chemcsk@gmail.com
› Author Affiliations
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Publication History

Received: 26 October 2016

Accepted after revision: 17 January 2017

Publication Date:
09 February 2017 (online)


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Abstract

A new strategy for the synthesis of benzothiophenes through formal [3+2] annulation of sulfanylacetaldehyde and cyclohexa-2,4-dien-1-one monoketals has been developed. This approach relies on the ease of aromatization of tetrahydrobenzothiophenone derivatives prepared by the aforementioned protocol. Given the ready accessibility of various substituted cyclohexa-2,4-dien-1-one monoketals, a range of benzothiophene derivatives became available.

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