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
收藏
页码：5643 / 5659
页数：17
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