Radical Cyclization of Ynamides to Nitrogen Heterocycles

被引：3

作者：

Zhang, Chunyang ^{[1
,2
]}

Blanchard, Nicolas ^{[2
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] Univ Libre Bruxelles ULB, Lab Chim Organ, Serv Chim & Physicochim Organ, Ave FD Roosevelt 50,CP160-06, B-1050 Brussels, Belgium

[2] Univ Strasbourg, Univ Haute Alsace, CNRS, LIMA,UMR 7042, F-68000 Mulhouse, France

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 02期

关键词：

ynamides; radical cyclization; pyrrolidines; heterocycles; ring closure; KETENIMINIUM IONS; GENERAL-SYNTHESIS; ALKYNES; RULES; PHENANTHROINDOLIZIDINE; ALKYNYLATION; NUCLEOPHILES; PIPERIDINES; AMIDATIONS; PRECURSORS;

D O I：

10.1055/a-1868-8092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 degrees 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.

引用

收藏

页码：272 / 288

页数：17

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