Dimethyl Sulfoxide and N-Iodosuccinimide Promoted 5-exo-dig Oxidative Cyclization of Yne-Tethered Ynamide: Access to Pyrrolidones and Spiro-pyrrolidones

被引：31

作者：

Prabagar, B. ^{[1
]}

Nayak, Sanatan ^{[1
]}

Prasad, Rangu ^{[1
]}

Sahoo, Akhila K. ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 13期

关键词：

SILYL ENOL ETHERS; ENDO; IODOCYCLIZATION; DERIVATIVES; IODINATION; ALKYNES;

D O I：

10.1021/acs.orglett.6b01149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented metal-free dimethyl sulfoxide (DMSO) and N-iodosuccinimide mediated regioselective 5-exo-dig oxidative cyclization of an in situ generated enol equivalent of amides from ynamides bearing internal alkynes is demonstrated. The reaction allows easy access to functionalized pyrrolidone skeletons. Pyrrolidones having 3-o-biaryl motifs successfully undergo intramolecular electrophilic cyclization with the alpha,beta-unsaturated olefin, furnishing spiro-pyrrolidone motifs. A one-pot sequential 5-exo-dig cyclization of the yne-tethered ynamides, followed by electrophilic cyclization of the pyrrolidone, is presented. The role of DMSO in the transformation is clarified, and a tentative reaction pathway is proposed.

引用

页码：3066 / 3069

页数：4

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