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Base-promoted aerobic oxidation of N-alkyl iminium salts derived from isoquinolines and related heterocycles

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Abstract

Potassium tert-butoxide-promoted aerobic oxidation of N-alkyl iminium salts is reported. The reaction is atom-economical and environmentally friendly. Iminium salts derived from isoquinoline, quinoline, phenanthridine, phenanthroline, and phthalazine were successfully transformed into their corresponding unsaturated lactams with up to 95% yield under mild conditions in the absence of photocatalysts and metallic or organic catalysts. Owing to the general substrate scope, low cost, feasibility of scale up, wide availability of reagents, and green reaction conditions, this method shows great potential for preparing isoquinolones and related compounds. The method was applied for atom- and step-economical total synthesis of natural products such as norketoyobyrine.

Graphical abstract: Base-promoted aerobic oxidation of N-alkyl iminium salts derived from isoquinolines and related heterocycles

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Publication details

The article was received on 22 Oct 2019, accepted on 28 Nov 2019 and first published on 28 Nov 2019


Article type: Paper
DOI: 10.1039/C9GC03629F
Green Chem., 2020, Advance Article

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    Base-promoted aerobic oxidation of N-alkyl iminium salts derived from isoquinolines and related heterocycles

    L. Bai, Y. Zhou, X. Zhuang, L. Zhang, J. Xue, X. Lin, T. Cai and Q. Luo, Green Chem., 2020, Advance Article , DOI: 10.1039/C9GC03629F

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