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Palladium‐Catalyzed Selective Synthesis of Dibenzo[ c , e ]azepin‐5‐ols and Benzo[ c ]pyrido[2,3‐ e ]azepin‐5‐ols
Author(s) -
Yao Xinrong,
Shao Yinlin,
Hu Maolin,
Zhang Maosheng,
Li Shaotong,
Xia Yuanzhi,
Cheng Tianxing,
Chen Jiuxi
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900705
Subject(s) - chemistry , palladium , tandem , catalysis , stereochemistry , medicinal chemistry , selectivity , organic chemistry , materials science , composite material
An efficient palladium‐catalyzed tandem addition/cyclization of 2′‐formyl‐[1,1′‐biaryl]‐2‐carbonitriles with arylboronic acids is reported. This reaction affords dibenzo[ c , e ]azepin‐5‐ols and benzo[ c ]pyrido[2,3‐ e ]azepin‐5‐ols with excellent selectivity and wide functional group compatibility. The dibenzo[ c , e ]azepin‐5‐ols show good cell growth inhibitory activity against a triple‐negative breast cancer cell line. Moreover, the proposed mechanistic rationale for this tandem process is supported by theoretical calculations.