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
收藏
页码：3798 / 3808
页数：11
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