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Issue 26, 2018
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A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using Fischer indolization

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Abstract

A number of 2-(hetero)aryl-substituted thieno[3,2-b]indoles have been successfully prepared using an efficient transition-metal-free strategy, involving the Fiesselmann synthesis of methyl 5-(hetero)aryl-3-hydroxythiophene-2-carboxylates from 2-bromo-3-(hetero)arylacrylates and methyl thioglycolate, and the transformation of the synthesized 3-hydroxyesters into the corresponding thiophen-3(2H)-ones, followed by their treatment with arylhydrazines to directly form the targeted structures via Fischer indolization. At the same time, structural variety of the obtained thieno[3,2-b]indoles has been achieved due to a wide range of available starting materials, including both 2-bromo-3-(hetero)arylacrylates and arylhydrazines. In addition, two π-extended molecules, namely 1,4-bis(4H-thieno[3,2-b]indol-2-yl)benzene and 2,5-bis(4H-thieno[3,2-b]indol-2-yl)thiophene, have been synthesized in line with the current approach towards 2-(hetero)arylated thieno[3,2-b]indoles.

Graphical abstract: A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using Fischer indolization

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Publication details

The article was received on 11 May 2018, accepted on 08 Jun 2018 and first published on 08 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01110A
Citation: Org. Biomol. Chem., 2018,16, 4821-4832
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    A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using Fischer indolization

    R. A. Irgashev, A. S. Steparuk and G. L. Rusinov, Org. Biomol. Chem., 2018, 16, 4821
    DOI: 10.1039/C8OB01110A

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