Palladium‐Catalyzed Selective Synthesis of Dibenzo[c,e]azepin‐5‐ols and Benzo[c]pyrido[2,3‐e]azepin‐5‐ols

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 dib...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-10, Vol.361 (20), p.4707-4713
Main Authors: Yao, Xinrong, Shao, Yinlin, Hu, Maolin, Zhang, Maosheng, Li, Shaotong, Xia, Yuanzhi, Cheng, Tianxing, Chen, Jiuxi
Format: Article
Language:English
Subjects:
benzo[c]pyrido[2,3-e]azepin-5-ols
dibenzo[c,e]azepin-5-ols
nitriles
palladium-catalyzed
tandem reaction
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900705