A Green Approach for 1, 2, 3‐Triazole‐Fused Quinolinones via Metal‐Free Cascade [3+2] Cycloaddition/C‐N Coupling Reaction. Issue 31 (18th August 2022)

• Record Type: Journal Article
• Authors: Majeed, Kashif; Zhou, Fengtao; Liu, Chaoyi; Guo, Zijian; Dong, Penghui; Zhang, Qiuyu
• Is Part Of: ChemistrySelect. Volume 7:Issue 31(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-18
• Subjects: [3+2] Cycloaddition -- 1, 2, 3-Triazole-fused Quinolinone -- C−N Bond formation -- Metal-free -- Sodium azide -- Tandem reaction; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202200978
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A metal‐free cascade reaction of 1‐(8‐halonaphthalen‐1‐yl)prop‐2‐yn‐1‐ones with sodium azide has been developed for the construction of quinolinone fused triazole frameworks. The reaction proceeded smoothly via an intramolecular metal‐free version of the azide‐alkyne [3 + 2] cycloaddition. A variety of quinolinone fused triazole derivatives were prepared in good to excellent yields under metal‐free conditions. The practicality of this metal‐free protocol was further evaluated by gram scale synthesis of quinolinone fused triazole derivatives. Abstract : This study describes a green and straightforward method for the synthesis of novel 1, 2, 3‐triazole‐fused quinazolinones through an intramolecular metal‐free version of the azide‐alkyne [3 + 2] cycloaddition reaction followed by C−N coupling process. Simple reaction procedure, great functional group tolerance and high yield are some salient features of this green methodology.