Benzoic Acid‐Promoted Intermolecular [3+2] Cycloaddition with Air as the Terminal Oxidant: General Approach toward Pyrrolo[2,  1‐a]isoquinolines. Issue 33 (24th November 2017)

• Record Type: Journal Article
• Authors: Zheng, Kailu; Zhuang, Shiyi; You, Minqi; Shu, Wenming; Wu, Anxin; Wu, Yandong
• Is Part Of: ChemistrySelect. Volume 2:Issue 33(2017)
• Page Start: 10762
• Page End: 10765
• Publication Date: 2017-11-24
• Subjects: 1, 3-dipolar cycloaddition -- in situ-generated azomethine ylide -- metal-free reaction -- one-pot construction -- pyrrolo[2, 1-a]isoquinolines; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201702044
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A novel benzoic acid‐promoted intermolecular 1, 3‐dipolar cycloaddition reaction has been developed for the one‐pot construction of biologically important pyrrolo[2, 1‐ a ]isoquinolines. This metal‐free reaction between dipolarophiles and in situ‐generated azomethine ylides avoids the pre‐preparation of N‐substituted substrates and allows for the efficient formation of one C−N bond and two C−C bonds. Abstract : In this manuscript, we developed a benzoic acid mediated intermolecular 1, 3‐dipolar addition for the construction of pyrrolo[2, 1‐ a ]isoquinoline derivatives via capturing the azomethine ylides generated in situ from 1, 2, 3, 4‐tetrahydroisoquinoline (THIQ) and arylglyoxal monohydrates. This metal‐free protocol utilizes air as the terminal oxidant, which provides a green and atom economic access to pyrrolo[2, 1‐ a ]isoquinolines in high yields under mild conditions.