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Synthesis 2018; 50(17): 3467-3486
DOI: 10.1055/s-0037-1609857
DOI: 10.1055/s-0037-1609857
paper
Synthesis of Various Heterocycles Having a Dienamide Moiety by Ring-Closing Metathesis of Ene-ynamides
Authors
Further Information
Publication History
Received: 23 March 2018
Accepted after revision: 23 April 2018
Publication Date:
30 May 2018 (online)
Abstract
Ring-closing metathesis (RCM) of ynamides, having alkene substituents of various lengths on the side chain, was demonstrated using the second-generation Grubbs catalyst. When the reaction of ene-ynamides was carried out in the presence of 5 mol% of the catalyst, RCM proceeded smoothly to give quinoline or isoquinoline derivatives having a dienamide unit in good yields. Furthermore, RCM of ene-ynamides, having one more carbon on the side chain, proceeded smoothly to provide seven-membered heterocycles having a dienamide component. Similarly, eight-membered heterocycles, diazocine and benzodiazocine, were also synthesized by RCM of ene-ynamides in good yields.
Key words
ruthenium carbene complex - ynamide - ring-closing metathesis - heterocycles - medium-sized ringSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609857.
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