Access to 2‐Arylquinazolin‐4(3H)‐ones through Intramolecular Oxidative C(sp3)−H/N−H Cross‐Coupling Mediated by I2/DMSO. Issue 4 (26th November 2021)

• Record Type: Journal Article
• Authors: Wen, Simiaomiao; Du, Yifan; Liu, Yiwen; Cui, Xiaofeng; Liu, Qixing; Zhou, Haifeng
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 4(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2021-11-26
• Subjects: 2-Arylquinazolin-4(3H)-one -- 2-(Benzylamino)benzamide -- C−N bond formation -- Cross-coupling -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202101187
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A novel approach for the synthesis of 2‐arylquinazolin‐4(3H)‐ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2 /DMSO‐mediated intramolecular oxidative cross‐coupling of 2‐(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram‐scale synthesis. A proposed reaction pathway based on some control experiments was also provided. Abstract : A practical approach for preparing 2‐arylquinazolin‐4(3H)‐ones by an I2/DMSO‐mediated intramolecular oxidative cross‐coupling of 2‐(benzylamino)benzamides to form C=N bonds has been developed.