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On the formation of seven-membered rings by arene-ynamide cyclization.

ABSTRACT:

Abstract

A Brønsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior.

Graphical abstract

SUBMITTER: Brutiu BR

PROVIDER: S-EPMC6320749 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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On the formation of seven-membered rings by arene-ynamide cyclization.

Brutiu Bogdan R BR Bubeneck Wilhelm Andrei WA Cvetkovic Olivera O Li Jing J Maulide Nuno N

Monatshefte fur chemie 20181116 1

<h4>Abstract</h4>A Brønsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior.<h4>Graphical abstract</h4> ...[more]

PMID: 30662090

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