Copper-catalyzed tandem cyclization of 2-(2-iodophenyl)imidazo[1,2-a] pyridine derivatives with selenium: Synthesis of benzo[b]selenophene-fused imidazo[1,2-a]pyridines

被引：21

作者：

Matsumura, Mio ^{[1
]}

Sakata, Yumi ^{[1
]}

Iwase, Atsuya ^{[1
]}

Kawahata, Masatoshi ^{[2
]}

Kitamura, Yuki ^{[1
]}

Murata, Yuki ^{[1
]}

Kakusawa, Naoki ^{[3
]}

Yamaguchi, Kentaro ^{[2
]}

Yasuike, Shuji ^{[1
]}

机构：

[1] Aichi Gakuin Univ, Sch Pharmaceut Sci, Chikusa Ku, 1-100 Kusumoto Cho, Nagoya, Aichi 4648650, Japan

[2] Tokushima Bunri Univ, Pharmaceut Sci Kagawa Campus, 1314-1 Shido, Sanuki, Kagawa 7692193, Japan

[3] Hokuriku Univ, Fac Pharmaceut Sci, Ho 3 Kanagawa Machi, Kanazawa, Ishikawa 9201181, Japan

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 49期

关键词：

Benzo[b]selenophene-fused imidazo[1,2-a; pyridine; Selenium; Copper catalyst; Tandem cyclization; Imidazo[1,2-a]pyridine; C-H BOND; ARYL HALIDES; DIRECT ARYLATION; ORGANOSELENIUM CHEMISTRY; COUPLING REACTION; DIARYL SELENIDES; EFFICIENT; COMPLEXES; IODIDE; SE;

D O I：

10.1016/j.tetlet.2016.10.095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu-catalyzed tandem cyclization of 2-(2-iodophenyl)imidazo[1,2-a]pyridines with selenium for the practical synthesis of the benzo[b]selenophene-fused imidazo[1,2-a]pyridines occurred smoothly via Ullmann-type Se-arylation and C-sp2-H selenation. A variety of benzo[b]selenophene-fused imidazo[1,2a]pyridines were easily obtained in moderate-to-high yields. Single-crystal X-ray analysis of 2a revealed that the benzo[b]selenophene and imidazopyridine rings are almost coplanar. The maximum absorption of tetracyclic compound 2a was red-shifted by 45-47 nm from those of imidazo[1,2-a]pyridine and benzo [b]selenophene.

引用

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页码：5484 / 5488

页数：5

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