Alkylation/Ipso-cyclization of Active Alkynes Leading to 3-AlkylatedAza- and Oxa-spiro[4,5]-trienones

被引：22

作者：

Chen, Pu ^{[1
]}

Fan, Jian-Hong ^{[1
]}

Yu, Wen-Qin ^{[1
]}

Xiong, Bi-Quan ^{[1
]}

Liu, Yu ^{[1
]}

Tang, Ke-Wen ^{[1
]}

Xie, Jun ^{[1
]}

机构：

[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 09期

基金：

中国国家自然科学基金;

关键词：

INTRAMOLECULAR IPSO-HALOCYCLIZATION; METAL-FREE; RADICAL CYCLIZATION; N-ARYLPROPIOLAMIDES; CINNAMAMIDES ACCESS; HANTZSCH ESTERS; DEAROMATIZATION; SPIROCYCLIZATION; N-(P-METHOXYARYL)PROPIOLAMIDES; 4-ALKYL-1,4-DIHYDROPYRIDINES;

D O I：

10.1021/acs.joc.1c03118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the preparation of 3-alkylated spiro[4.5]trienonesviaalkylation/ipso-cyclization of activated alkyneswith 4-alkyl-DHPs under transition-metal-free conditions is proposed. This alkylation successively undergoes the generation of alkylradicals, addition of alkyl radicals to the alkynes, and intramolecular ipso-cyclization. The mechanism studies suggest that thealkylation/ipso-cyclization involves a radical process. This ipso-cyclization procedure shows a series of advantages, such asaccessibility, mild conditions, high efficiency, greater safety, and an environmentally friendly method

引用

页码：5643 / 5659

页数：17

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