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Issue 36, 2017
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Regioselective oxidative cross-coupling of benzo[d]imidazo[2,1-b]thiazoles with styrenes: a novel route to C3-dicarbonylation

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Abstract

A novel I2 promoted, highly efficient metal-free and peroxide-free greener domino protocol for the C3-dicarbonylation of benzo[d]imidazo[2,1-b]thiazoles (IBTs) with styrenes has been developed via oxidative cleavage of the C(sp2)–H bond, followed by C3-nucleophilic attack of IBT and oxidation. Interestingly, under these conditions 2-(benzo[d]imidazo[2,1-b]thiazol-2-yl)aniline gave the benzo[4′,5′]thiazolo[2′,3′:2,3]imidazo[4,5-c]quinoline derivative via oxidative cleavage of the C(sp2)–H bond, followed by Pictet–Spengler cyclization and aromatization. This method offers the advantages of broad substrate scope, ecofriendly feature and high atom economy apart from higher yields.

Graphical abstract: Regioselective oxidative cross-coupling of benzo[d]imidazo[2,1-b]thiazoles with styrenes: a novel route to C3-dicarbonylation

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Publication details

The article was received on 19 Jul 2017, accepted on 24 Aug 2017 and first published on 05 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB01778B
Citation: Org. Biomol. Chem., 2017,15, 7696-7704
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    Regioselective oxidative cross-coupling of benzo[d]imidazo[2,1-b]thiazoles with styrenes: a novel route to C3-dicarbonylation

    S. P. Shaik, F. Sultana, A. Ravikumar, S. Sunkari, A. Alarifi and A. Kamal, Org. Biomol. Chem., 2017, 15, 7696
    DOI: 10.1039/C7OB01778B

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