Radical Cyclization of Ynamides to Nitrogen Heterocycles

Chunyang Zhang; Nicolas Blanchard; Gwilherm Evano

doi:10.1055/a-1868-8092

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(02): 272-288
DOI: 10.1055/a-1868-8092

paper

Special Issue dedicated to Prof. Alain Krief

Radical Cyclization of Ynamides to Nitrogen Heterocycles

Chunyang Zhang

^aLaboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium

^bUniversité de Haute-Alsace, Université de Strasbourg, CNRS,LIMA, UMR 7042, 68000 Mulhouse, France

,

Nicolas Blanchard

^bUniversité de Haute-Alsace, Université de Strasbourg, CNRS,LIMA, UMR 7042, 68000 Mulhouse, France

,

Gwilherm Evano ∗

^aLaboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Dedicated to Prof. Alain Krief on the occasion of his 80^th 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.

Key words

ynamides - radical cyclization - pyrrolidines - heterocycles - ring closure

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Referenzen

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Zusatzmaterial

Supporting Information