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Synthesis 2023; 55(02): 272-288
DOI: 10.1055/a-1868-8092
DOI: 10.1055/a-1868-8092
paper
Special Issue dedicated to Prof. Alain Krief
Radical Cyclization of Ynamides to Nitrogen Heterocycles
Our work was supported by the Université libre de Bruxelles (ULB) and the Région de Bruxelles-Capitale - Innoviris (2019-BRIDGE-5 PhotoCop). C.Z. acknowledges the China Scholarship Council (CSC) for a graduate fellowship.
Dedicated to Prof. Alain Krief on the occasion of his 80th birthday
Abstract
An efficient radical cyclization of suitably functionalized ynamides to nitrogen-containing heterocycles is reported. Upon reaction with tributyltin hydride in the presence of catalytic amounts of AIBN in toluene at 80 °C, a range of ynamides bearing a N-iodopropyl chain could be smoothly cyclized, in a highly regio- and stereoselective manner, to the corresponding 2-arylidenepyrrolidines in good to excellent yields. The exocyclic double bond was in addition shown to be an excellent anchor for further chemical diversification and the generality of this radical cyclization could be highlighted by its extension to the synthesis of other nitrogen heterocycles including piperidines, azepanes, pyrazolidines and hexahydropyridazines.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1868-8092.
- Supporting Information
Publication History
Received: 04 May 2022
Accepted after revision: 03 June 2022
Accepted Manuscript online:
03 June 2022
Article published online:
12 July 2022
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