Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates

Mandal, Tirtha ; Chakraborti, Gargi ; Karmakar, Shilpi ; Dash, Jyotirmayee (2018) Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates Organic Letters, 20 (16). pp. 4759-4763. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.8b01827

Related URL: http://dx.doi.org/10.1021/acs.orglett.8b01827

Abstract

The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.

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Deposited On:17 Oct 2022 05:43
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