Synthesis of 1-(1H-Tetrazol-5-yl)-2H-isoindole Derivatives through Ugi Four-Component and Silver-Catalyzed Reactions

A facile and efficient one‐pot, two‐step synthesis of 1,2‐disubstituted 3‐(1H‐tetrazol‐5‐yl)‐2H‐isoindoles through Ugi four‐component reaction/AgNO3‐catalyzed reaction of 2‐alkynylbenzaldehydes, amines, isonitriles, and Me3SiN3 is described. This transformation proceeds through 5‐exo‐dig cyclization...

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Veröffentlicht in:European journal of organic chemistry 2014-06, Vol.2014 (16), p.3379-3386
Hauptverfasser: Wu, Ran, Gao, Shang, Chen, Xu, Yang, Guanghui, Pan, Lingling, Hu, Gaobo, Jia, Ping, Zhong, Weihui, Yu, Chuanming
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Sprache:eng
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Zusammenfassung:A facile and efficient one‐pot, two‐step synthesis of 1,2‐disubstituted 3‐(1H‐tetrazol‐5‐yl)‐2H‐isoindoles through Ugi four‐component reaction/AgNO3‐catalyzed reaction of 2‐alkynylbenzaldehydes, amines, isonitriles, and Me3SiN3 is described. This transformation proceeds through 5‐exo‐dig cyclization, [1,3]‐H shift, and [1,5]‐H shift to generate the products in moderate to excellent yields. A one‐pot, two‐step synthesis of 1‐(1H‐tetrazol‐5‐yl)‐2H‐isoindole derivatives through Ugi four‐component reaction/AgNO3‐catalyzed reaction of 2‐alkynylbenzaldehydes, amines, isonitriles, and Me3SiN3 has been developed. The transformation proceeds through 5‐exo‐dig cyclization, [1,3]‐H shift, and [1,5]‐H shift to generate the products in moderate to excellent yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201402098