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Aerobic, metal-free synthesis of 6H-chromeno[4,3-b]quinolin-6-ones.

ABSTRACT: A Friedländer-based method for transition-metal free, aerobic synthesis of chromene-fused quinolinones is reported. The coupling of 4-hydrocoumarins and 2-aminobenzyl alcohols proceeds in the presence of acetic acid solvent and oxygen oxidant, affording 6H-chromeno[4,3-b]quinolin-6-ones in good to excellent yields. The reactions are tolerant of functionalities such as alkyl, methoxy, bromo, chloro, and N-heterocycle. Isosteric cyclic 1,3-diketones and 2-amino acetophenones also give fused quinolinones under reaction conditions. The method herein offers a rapid and benign synthesis of hitherto challenging N-heterocycles. To our best knowledge, such a convenient pathway to obtain chromene-fused quinolinones have not been known in the literature.

SUBMITTER: Ton NNH

PROVIDER: S-EPMC9064357 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Aerobic, metal-free synthesis of 6H-chromeno[4,3-b]quinolin-6-ones.

Ton Nhan N H NNH Dang Ha V HV Phan Nam T S NTS Nguyen Tung T TT

RSC advances 20190523 28

A Friedländer-based method for transition-metal free, aerobic synthesis of chromene-fused quinolinones is reported. The coupling of 4-hydrocoumarins and 2-aminobenzyl alcohols proceeds in the presence of acetic acid solvent and oxygen oxidant, affording 6H-chromeno[4,3-b]quinolin-6-ones in good to excellent yields. The reactions are tolerant of functionalities such as alkyl, methoxy, bromo, chloro, and N-heterocycle. Isosteric cyclic 1,3-diketones and 2-amino acetophenones a ...[more]

PMID: 35521415

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