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Issue 43, 2018
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Solvent and catalyst free ring expansion of indoles: a simple synthesis of highly functionalized benzazepines

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Abstract

Highly functionalized benzazepines have been synthesized by using various substituted indoles and dialkylacetylene dicarboxylates under thermal and open air conditions. The reaction was carried out in a solvent and under catalyst free conditions and the products are formed in very good yields. The reaction proceeds in a concerted fashion thus providing potentially bioactive benzazepines by ring expansion of a five-membered indole ring. It is also described that the ring contraction of seven-membered benzazepines in the presence of KOtBu base at room temperature smoothly afforded the corresponding 3-alkenylated indole derivatives in very good yields.

Graphical abstract: Solvent and catalyst free ring expansion of indoles: a simple synthesis of highly functionalized benzazepines

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Publication details

The article was received on 29 Jul 2018, accepted on 11 Oct 2018 and first published on 11 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB01825A
Citation: Org. Biomol. Chem., 2018,16, 8160-8168

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    Solvent and catalyst free ring expansion of indoles: a simple synthesis of highly functionalized benzazepines

    M. Bakthadoss, P. V. Kumar, T. T. Reddy and D. S. Sharada, Org. Biomol. Chem., 2018, 16, 8160
    DOI: 10.1039/C8OB01825A

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