Palladium‐Catalyzed Carbonylative Difunctionalization of C=N Bond of Azaarenes or Imines to Quinazolinones

• Published in: Chemistry, an Asian journal Vol. 15; no. 11; pp. 1678 - 1682
• Main Authors: Zhou, Xibing, Ding, Yongzheng, Huang, Hanmin
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 02.06.2020
• Subjects: Alcohols; Amines; carbonylation; Carbonyls; Chemistry; cyclization; difunctionalization; Imines; Palladium; quinazolinone; Quinazolinones; Synthesis; quinazolinone; difunctionalization; palladium; carbonylation; cyclization
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.202000359

Supporting information for this article is given via a link at the end of the document. By intercepting the acylpalladium species with C=N bond of azaarenes or imines other than free amines or alcohols, the difunctionalization of C=N bond was established via palladium‐catalyzed carbonylation/nucleophilic addition sequence. This method is compatible with a diverse range of azaarenes and imines and allows for the efficient synthesis of a wide range of quinazolinones and derivatives. The synthetic utility has been demonstrated by one‐step synthesis of evodiamine and its analogue with inexpensive starting materials. Palladium‐catalyzed carbonylative difunctionalization of C=N bond of azaarenes and imines has been reported that provides a reliable and rapid approach to quinazolinones. The synthetic utility of this reaction has further been demonstrated by its application to one‐step synthesis of rutaecarpin and evodiamine from inexpensive and commercially available materials.