Base-promoted fused β-carboline formation from 2-(1<i>H</i>-indol-3-yl)cyclohexan-1-ones, aldehydes and ammonium salts

Chen, Jinjin; Zhang, Yu; Liu, Xinping; Liu, Kang; Wu, Junting; Peng, Xinlei; Deng, Guo-Jun

doi:10.1039/d4qo00551a

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00551a

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Base-promoted fused β-carboline formation from 2-(1H-indol-3-yl)cyclohexan-1-ones, aldehydes and ammonium salts

Jinjin Chen,

Yu Zhang,

Xinping Liu

et al.

Abstract: A novel base-promoted fused β-carboline formation strategy from 2-(1H-indol-3-yl)cyclohexan-1-ones, aldehydes and ammonium salts has been developed. In this cascade reaction, ammonium salts served as the convenient nitrogen source and simultaneously...

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Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing N-Heterocycles via Transforming C–H to C–OH Bonds

Guo,

Miao,

Zhao

et al. 2024

Org. Lett.

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We developed a molecular-oxygen-mediated multicomponent oxidative cyclization strategy to synthesize Nheterocycles containing tertiary alcohol units via the formation of key C−OH bonds and quaternary carbon centers. This formal [3 + 2 + 1] annulation offers a green and sustainable alternative for the de novo C−OH bond formation, using O 2 as both the oxidant and oxygen source under metal-and catalyst-free conditions. Notably, continuous [1,5]-hydrogen transfer together with excess alcohols promotes the formation of C−OH-bearing products. Additionally, the generation of quaternary carbon centers inhibits the conversion of C−OH bonds to C�O bonds, thus stabilizing the desired products.

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Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing N-Heterocycles via Transforming C–H to C–OH Bonds

Guo,

Miao,

Zhao

et al. 2024

Org. Lett.

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show abstract

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Base-promoted fused β-carboline formation from 2-(1H-indol-3-yl)cyclohexan-1-ones, aldehydes and ammonium salts

Abstract: A novel base-promoted fused β-carboline formation strategy from 2-(1H-indol-3-yl)cyclohexan-1-ones, aldehydes and ammonium salts has been developed. In this cascade reaction, ammonium salts served as the convenient nitrogen source and simultaneously...

Cited by 1 publication

References 48 publications

Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing N-Heterocycles via Transforming C–H to C–OH Bonds

Molecular-Oxygen-Mediated Multicomponent Oxidative Cyclization: Synthesis of Tertiary-Alcohol-Unit-Bearing N-Heterocycles via Transforming C–H to C–OH Bonds

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