Synthesis of 1,4-Dihydropyridines and Related Heterocycles by Iodine-Mediated Annulation Reactions of N‑Cyclopropyl Enamines

The annulation of N-cyclopropyl enamines to produce 1,4-dihydropyridine (1,4-DHP) derivatives is described. In the presence of molecular iodine (I2), an N-cyclopropyl enamine substrate undergoes iodination, opening of the cyclopropyl ring, and annulation with a second molecule of the substrate to fo...

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Bibliographic Details
Published in:Organic letters 2021-12, Vol.23 (24), p.9625-9630
Main Authors: Wei, Lanlan, Wang, Manman, Zhao, Yifei, Fang, Yingchao, Zhao, Zongxiang, Xia, Biao, Yu, Wenquan, Chang, Junbiao
Format: Article
Language:English
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Summary:The annulation of N-cyclopropyl enamines to produce 1,4-dihydropyridine (1,4-DHP) derivatives is described. In the presence of molecular iodine (I2), an N-cyclopropyl enamine substrate undergoes iodination, opening of the cyclopropyl ring, and annulation with a second molecule of the substrate to form the 1,4-DHP product. This reaction is amenable to gram-scale operations under mild reaction conditions with no transition metals being required. Further transformations of the 1,4-DHPs leads to related pyridine and bicyclic frameworks.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03859