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Issue 14, 2017
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Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion

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Abstract

Imidazoline-fused [1,4]oxazepines (prepared in two simple steps from methyl 2-hydroxyaroates, ethylene diamine and bis-electrophilic aromatics) undergo a facile, good-yielding hydrolytic imidazoline ring expansion (HIRE) upon N-alkylation and treatment with aqueous K2CO3. The resulting arene-fused ten-membered lactams significantly add to the contemporary arsenal of small-molecule scaffolds where medium-sized ring systems are severely underrepresented.

Graphical abstract: Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion

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Supplementary files

Article information


Submitted
10 Feb 2017
Accepted
12 Mar 2017
First published
15 Mar 2017

This article is Open Access

Org. Biomol. Chem., 2017,15, 2906-2909
Article type
Communication

Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion

A. Sapegin, A. Osipyan and M. Krasavin, Org. Biomol. Chem., 2017, 15, 2906
DOI: 10.1039/C7OB00535K

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