Application of N,N-Dimethylethanolamine as a One-Carbon Synthon for the Synthesis of Pyrrolo[1,2-a]quinoxalines, Quinazolin-4-ones, and Benzo[4,5]imidazoquinazolines via [5+1] Annulation

被引：15
|
作者：
Geng, Meiqi [1 ,2 ,3 ]
Huang, Minzhao [1 ,2 ]
Kuang, Jinqiang [1 ,2 ]
Fang, Weiwei [4 ]
Miao, MaoZhong [3 ]
Ma, Yongmin [1 ,2 ]
机构：
[1] Taizhou Univ, Inst Adv Studies, Taizhou 318000, Zhejiang, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut Sci, Taizhou 318000, Zhejiang, Peoples R China
[3] Zhejiang Sci Tech Univ, Dept Chem, Key Lab Surface & Interface Sci Polymer Mat Zheji, Hangzhou 310018, Peoples R China
[4] Nanjing Forestry Univ NFU, Coll Chem Engn, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 21期
关键词：
DIRECT AEROBIC CARBONYLATION; EFFICIENT SYNTHESIS; SYNERGISTIC CATALYSIS; OXIDATIVE SYNTHESIS; BRONSTED ACID; QUINAZOLINONES; DERIVATIVES; CONSTRUCTION; CYCLIZATION; ACTIVATION;
D O I：
10.1021/acs.joc.2c02079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of N-heterocycles composes a significant part of synthetic chemistry. In this report, a Cu(II)-catalyzed green and efficient synthesis of pyrrolo[1,2-a]quinoxaline, quinazolin-4-one, and benzo[4,5]imidazoquinazoline derivatives was developed, employing N,N-dimethylethanolamine (DMEA) as a C1 synthon. Green oxidant O-2 is critical in these transformations, facilitating the formation of a key intermediate-a reactive iminium ion. The method conducted under mild conditions is compatible with a diversity of functional groups, providing an appealing alternative to the previously developed protocols.
引用
收藏
页码：14753 / 14762
页数：10
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