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Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor.


ABSTRACT: We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.

SUBMITTER: Chang Z 

PROVIDER: S-EPMC7179414 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of <i>N</i>-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor.

Chang Zhe Z   Ma Tong T   Zhang Yu Y   Dong Zheng Z   Zhao Heng H   Zhao Depeng D  

Molecules (Basel, Switzerland) 20200309 5


We developed an efficient method for synthesis of substituted <i>N</i>-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted <i>N</i>-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including <i>N</i>-acetyl and <i>N</i>-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for <i>N</i>-benzoylindole over benzoxazine, and this is the first example of Pd(II  ...[more]

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