Nickel(II)-Catalyzed [5+1] Annulation of 2-Carbonyl-1-propargylindoles with Hydroxylamine To Synthesize Pyrazino[1,2-a]indole-2-oxides in Water

被引：18

作者：

Bi, Hong-Yan ^{[1
]}

Du, Min ^{[1
]}

Pan, Cheng-Xue ^{[1
]}

Xiao, Yuhong ^{[2
]}

Su, Gui-Fa ^{[1
]}

Mo, Dong-Liang ^{[1
]}

机构：

[1] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, State Key Lab Chem & Mol Engn Med Resources, Minist Sci & Technol China, 15 Yu Cai Rd, Guilin 541004, Peoples R China

[2] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 16期

基金：

中国国家自然科学基金;

关键词：

CONJUGATE ADDITION METHODOLOGY; H BOND; ALKYNYLCARBONYL COMPOUNDS; TANDEM REACTION; CYCLOADDITION; CONSTRUCTION; EFFICIENT; AMINATION; KETONES; OXIMES;

D O I：

10.1021/acs.joc.9b00784

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An atom-economical and practical method for the efficient synthesis of various pyrazino[1,2-a]indole-2-oxides was developed through a nickel(II)-catalyzed [5 + 1] annulation of 2-carbonyl-1-propargylindoles with hydroxylamine in water without using an organic solvent. The reaction involved an initial condensation of 2-carbonyl-1-propargylindoles with hydroxylamine to afford oxime intermediates, which then underwent a nickel(II)-catalyzed 6-exo-dig cyclization. Preliminary studies showed that (n-Bu)(4)NI served as a phase transfer catalyst and promoted the formation of active nickel(II) species. More importantly, the nickel(II) salt and phase transfer catalyst-in-water could be recycled seven times, and a gram scalable product was easily obtained in good yields through a filtration and washing protocol.

引用

收藏

页码：9859 / 9868

页数：10

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