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Review | Regular issue | Vol 100, No. 3, 2020, pp.321-369
Published online, 8th January, 2020
DOI: 10.3987/REV-19-918
Synthesis of Heterocycles Utilizing N-Alkoxyimines and Amides

Motohiro Yasui, Norihiko Takeda, and Masafumi Ueda*

*Department of Medicinal Chemistry, Kobe Pharmaceutical University, 4-19-1, Motoyamakitamachi, Higashinada, Kobe 658-8558, Japan


N-Alkoxyimines and amides are unique functional groups bearing adjacent N-O bonds. Alkynes having an N-alkoxyimine or amide group generate reactive vinyl metal species through activation by a transition metal catalyst to synthesize heterocycles. This approach, which allows various sequential reactions, can be expected to directly form a complex heterocycle from a simple starting material under mild conditions. Meanwhile, these kinds of reactions require chemoselectivity between the N- and O-atoms at the nucleophilic site and/or regioselectivity at the electrophilic alkyne moiety. This review introduces intramolecular nucleophilic addition of N-alkoxyimines/amides into an alkyne moiety, followed by various transformations to synthesize heterocycles.