Metal‐Free Catalyzed Cyclization of N‐Methoxybenzamides to Construct Quaternary Carbon‐Containing Isoindolinones

• Published in: Chinese journal of chemistry Vol. 39; no. 4; pp. 903 - 908
• Main Authors: Zhang, Lin‐Bao, Wang, Zi‐Chen, Sun, Sheng‐Zheng, Ni, Shao‐Fei, Wen, Li‐Rong, Li, Ming
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 01.04.2021; Wiley; Wiley Subscription Services, Inc
• Subjects: Alkynes; Annulation; Catalysts; Chemistry; Chemistry, Multidisciplinary; Computer applications; Density functional theory; Functional groups; Physical Sciences; Quaternary carbe; Regioselectivity; Science & Technology; Synthetic methods; Quaternary carbe; Density functional theory; Synthetic methods; Annulation; Alkynes
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.202000534

Main observation and conclusion Through the intramolecular cyclization of N‐methoxybenzamides, a simple and efficient method for constructing valuable isoindolinones under metal‐free conditions was developed. The reaction was featured by employing low‐cost catalyst, simple operation, 100% atomic economy and excellent regioselectivity. Moreover, a detailed computational study on the reaction system has been performed to clarify the mechanism. This protocol tolerated a variety of functional groups and provided a metal‐free protocol for the synthesis of chromane‐ or tetrahydroquinoline‐fused isoindolinones in good yields. Through the intramolecular cyclization of N‐methoxybenzamides, a simple and efficient method for constructing valuable isoindolinones under metal‐free conditions was developed. The reaction was featured by employing low‐cost catalyst, simple operation, 100% atomic economy and excellent regioselectivity. Moreover, a detailed computational study on the reaction system has been performed to clarify the mechanism. This protocol tolerated a variety of functional groups and provided a metal‐free protocol for the synthesis of chromane‐ or tetrahydroquinoline‐fused isoindolinones in good yields.