Synthesis of Benzo[4,5] imidazo[1,2-c] pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C-N Coupling and Cyclization

被引：28

作者：

Pham Duy Quang Dao ^{[1
]}

Lee, Ha Kyeong ^{[1
]}

Sohn, Ho-Sang ^{[2
]}

Yoon, Nam Sik ^{[3
]}

Cho, Chan Sik ^{[1
]}

机构：

[1] Kyungpook Natl Univ, Dept Appl Chem, 80 Daehakro, Daegu 702701, South Korea

[2] Kyungpook Natl Univ, Dept Mat Sci & Met Engn, 80 Daehakro, Daegu 702701, South Korea

[3] Kyungpook Natl Univ, Dept Text Syst Engn, 80 Daehakro, Daegu 702701, South Korea

来源：

ACS OMEGA | 2017年 / 2卷 / 06期

基金：

新加坡国家研究基金会;

关键词：

BETA-BROMO-ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; CARBONYLATIVE CYCLIZATION; ANTIMICROBIAL AGENTS; DOMINO SYNTHESIS; BUILDING-BLOCK; INHIBITORS; 2-AMINOPYRIMIDINES; PYRIMIDINES; CHEMISTRY; DISCOVERY;

D O I：

10.1021/acsomega.7b00693

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-(2-Bromovinyl) benzimidazoles and 2-(2bromophenyl) benzimidazoles react with cyanamide by microwave irradiation in dimethylformamide in the presence of a catalytic amount of CuI along with a base to give the corresponding benzo[4,5] imidazo[1,2-c] pyrimidin-1-amines and benzo[4,5] imidazo[1,2-c] quinazolin-6-amines, respectively, in moderate to good yields. 2-(2-Bromophenyl) indoles also react with cyanamide under similar conditions to afford indolo[1,2-c] quinazolin-6-amines. The reaction pathway seems to proceed via a sequence such as intermolecular C-N coupling, C-N formative cyclization, and tautomerization.

引用

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页码：2953 / 2958

页数：6

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