Room-temperature transition-metal-free one-pot synthesis of 3-aryl imidazo[1,2-a]pyridines via iodo-hemiaminal intermediate.
A mild and efficient one-pot synthesis of 3-aryl imidazo[1,2-a]pyridines in up to 88% yield was developed. An adduct was formed after the simple mixing of 2-amino-4-methylpyridine, 2-phenylacetaldehyde, and N-iodosuccinimide in CH2Cl2, and the structure of the adduct was characterized by 2D NMR, IR, and high-resolution mass analysis. The adduct was readily cyclized by treatment with a saturated aqueous solution of NaHCO3. The reactions proceeded to completion after several hours at room temperature.
Department of Chemistry and Institute of Functional Materials, Pusan National University, Busan 609-735, Korea.
Seul Ki
SK
Lee
Department of Chemistry and Institute of Functional Materials, Pusan National University, Busan 609-735, Korea.
Jin Kyoon
JK
Park
D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010847:Picolines / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry*; D013696:Temperature; D028561:Transition Elements / Q000737:chemistry*
D007093:Imidazoles; D010847:Picolines; D011725:Pyridines; D013388:Succinimides; D028561:Transition Elements; C015672:2-amino-4-picoline; C008155:N-iodosuccinimide