Room-temperature transition-metal-free one-pot synthesis of 3-aryl imidazo[1,2-a]pyridines via iodo-hemiaminal intermediate

The Journal of Organic Chemistry
Seul Ki Lee, Jin Kyoon Park

Abstract

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.

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Citations

Aug 11, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anna Kwiecień, Zbigniew Ciunik
Aug 27, 2015·Organic Letters·Praveen Reddy AdiyalaRam Awatar Maurya
Sep 9, 2016·The Journal of Organic Chemistry·Irwan Iskandar RoslanStephan Jaenicke
Jul 25, 2018·Organic & Biomolecular Chemistry·Zhiyuan HuJunbiao Chang
Mar 23, 2018·Beilstein Journal of Organic Chemistry·Irwan Iskandar RoslanStephan Jaenicke
Apr 16, 2020·Organic & Biomolecular Chemistry·Benyao FangJunbiao Chang

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