Tetrahedron

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

AK Nadipuram, SM Kerwin

Index: Nadipuram, Asha K.; Kerwin, Sean M. Tetrahedron, 2006 , vol. 62, # 16 p. 3798 - 3808

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Citation Number: 21

Abstract

Thermolysis of 1, 2-dialkynylimidazoles in chlorinated solvents leads to 5-chloroimidazo [1, 2-a]-pyridine products, which are also formed in DMF containing 1equiv of HCl. 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 ...