Catalyst‐Free One‐Pot Multi‐Component Synthesis of 2‐Substituted Quinazolin‐4‐carboxamides from 2‐Aminophenyl‐2‐oxoacetamides, Aldehydes, and Ammonium Acetate. Issue 22 (10th June 2021)

• Record Type: Journal Article
• Authors: Shim, Seung‐Hwan; Park, Hyejun; Mishra, Neeraj Kumar; Kim, In Su; Lee, Jae Kyun; Lee, Kiho; Jalani, Hitesh B.; Choi, Yongseok
• Is Part Of: ChemistrySelect. Volume 6:Issue 22(2021)
• Page Start: 5446
• Page End: 5450
• Publication Date: 2021-06-10
• Subjects: Carboxamide -- Catalyst-Free -- N-Heterocycles -- Multicomponent Reaction -- One-Pot Synthesis -- Quinazoline; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202100534
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Herein, we report a simple and straightforward catalyst‐free one‐pot multi‐component synthesis of quinazolin‐4‐carboxamides using 2‐(2‐aminophenyl)‐ N, N ‐dialkyl‐2‐oxoacetamide, aldehydes and ammonium acetate. As compared to the conventional approached for quinazolin‐4‐carboxamides synthesis, this transformation demonstrates very good reactivity by tolerating a large number of functional groups, and proceeds with good to moderate yields under mild conditions. Notably, the synthesized 6‐bromoquinazolin‐4‐carboxamide was subjected to Suzuki‐Miyaura cross‐coupling and Buchwald‐Hartwig C−N bond forming reactions providing a straightforward method to obtain structurally diverse and valuable quinazoline scaffolds. Furthermore, the reaction could be easily scaled up to gram scale. Abstract : With this novel one‐pot method using variety of aldehydes and 2‐aminophenyl‐2‐oxoacetamides, twenty eight novel quinazoline analogues were obtained in moderate to good yields. And it was applicable to a variety of quinazoline derivatives when 6‐bromoquinazolin‐4‐carboxamide was subjected to Suzuki‐Miyaura cross‐coupling and Buchwald‐Hartwig C−N bond forming reactions. Novel and facile one‐pot method in this work could be worth while applying to the synthesis of therapeutically valuable quinazoline derivatives.