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

页码：14753 / 14762

页数：10

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