Thermal cyclization of 1,2-dialkynylimidazoles to imidazo[1,2-a]pyridines

被引：24

作者：

Nadipuram, AK ^{[1
]}

Kerwin, SM ^{[1
]}

机构：

[1] Univ Texas, Div Med Chem, Coll Pharm, Inst Mol & Cellular Biol, Austin, TX 78712 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 16期

关键词：

aza-enediynes; cyclization; thermal rearrangement; carbenes; beta-chloroenamines;

D O I：

10.1016/j.tet.2005.11.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermolysis of 1,2-dialkynylimidazoles in chlorinated solvents leads to 5-chloroimidazo[1,2-a]-pyridine products, which are also formed in DMF containing 1 equiv of HCI. Deuterium labeling of the starting dialkynylimidazoles indicates that reaction may proceed by multiple pathways, depending upon conditions and substituents. Dialkynylimidazoles can also give rise to 5-diethylamino-substituted imidazopyridines when the thermolysis is carried out in the presence of diethylamine. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3798 / 3808

页数：11

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