Synthesis of 1‐(1H‐Tetrazol‐5‐yl)‐2H‐isoindole Derivatives through Ugi Four‐Component and Silver‐Catalyzed Reactions. Issue 16 (14th April 2014)

• Record Type: Journal Article
• Authors: Wu, Ran; Gao, Shang; Chen, Xu; Yang, Guanghui; Pan, Lingling; Hu, Gaobo; Jia, Ping; Zhong, Weihui; Yu, Chuanming
• Is Part Of: European journal of organic chemistry. Issue 16(2014)
• Page Start: 3379
• Page End: 3386
• Publication Date: 2014-04-14
• Subjects: Multicomponent reactions -- Cyclization -- Nitrogen heterocycles -- ­Alkynes -- Silver; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402098
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A facile and efficient one‐pot, two‐step synthesis of 1, 2‐disubstituted 3‐(1 H ‐tetrazol‐5‐yl)‐2 H ‐isoindoles through Ugi four‐component reaction/AgNO3 ‐catalyzed reaction of 2‐alkynylbenzaldehydes, amines, isonitriles, and Me3 SiN3 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. Abstract : A one‐pot, two‐step synthesis of 1‐(1 H ‐tetrazol‐5‐yl)‐2 H ‐isoindole derivatives through Ugi four‐component reaction/AgNO3 ‐catalyzed reaction of 2‐alkynylbenzaldehydes, amines, isonitriles, and Me3 SiN3 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.