Thermal cyclization of 1,2-dialkynylimidazoles to imidazo[1,2-a]pyridines |
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| Authors: | Asha K. Nadipuram |
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| Affiliation: | Division of Medicinal Chemistry, College of Pharmacy, Institute for Cellular and Molecular Biology, University of Texas at Austin, Austin, TX 78712, USA |
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| 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 1 equiv 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 the presence of diethylamine. |
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| Keywords: | Aza-enediynes Cyclization Thermal rearrangement Carbenes β-Chloroenamines |
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