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

Bakthadoss, Manickam and Kumar, Polu Vijay and Reddy, Tadiparthi Thirupathi and D S, Sharada (2018) Solvent and catalyst free ring expansion of indoles: a simple synthesis of highly functionalized benzazepines. Organic & Biomolecular Chemistry, 16 (43). pp. 8160-8168. ISSN 1477-0520

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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 (KOBu)-Bu-t base at room temperature smoothly afforded the corresponding 3-alkenylated indole derivatives in very good yields.

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IITH Creators:	IITH Creators ORCiD D S, Sharada UNSPECIFIED
Item Type:	Article
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	22 Jan 2019 06:14
Last Modified:	22 Jan 2019 06:14
URI:	http://raiithold.iith.ac.in/id/eprint/4742
Publisher URL:	http://doi.org/10.1039/c8ob01825a
OA policy:	http://www.sherpa.ac.uk/romeo/issn/1477-0520/
Related URLs:	Google Scholar

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