Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions

被引：16
|
作者：
Joseph, Devaneyan [1 ]
Park, Myeong Seong [1 ]
Lee, Sunwoo [1 ]
机构：
[1] Chonnam Natl Univ, Dept Chem, Gwangju 61186, South Korea
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 28期
基金：
新加坡国家研究基金会;
关键词：
H BOND-CLEAVAGE; N-C CLEAVAGE; SECONDARY AMIDES; CARBOXAMIDES; ACTIVATION;
D O I：
10.1039/d1ob00967b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.
引用
收藏
页码：6227 / 6232
页数：6
相关论文
共 50 条
  • [31] Direct Amination of Phenols under Metal-Free Conditions
    Yu, Jianzhong
    Wang, Yongtao
    Zhang, Peizhi
    Wu, Jun
    SYNLETT, 2013, 24 (11) : 1448 - 1454
  • [32] Oxidative Synthesis of Quinazolinones under Metal-free Conditions
    Feng, Jian-Bo
    Wu, Xiao-Feng
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (01) : 794 - 798
  • [33] I2-promoted aerobic oxidative coupling of acetophenes with amines under metal-free conditions: facile access to α-ketoamides
    Guo, Shiyu
    Fang, Zheng
    Yang, Zhao
    Liu, Chengkou
    Dai, Zhongxue
    Zhao, Lihuan
    Guo, Kai
    RSC ADVANCES, 2016, 6 (02): : 1503 - 1507
  • [34] Metal-Free Transamidation of Secondary Amides by N-C Cleavage
    Rahman, Md. Mahbubur
    Li, Guangchen
    Szostak, Michal
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (18): : 12091 - 12100
  • [35] One-Pot Synthesis of Quinoxalines Starting from Aldehydes Under Metal-Free Conditions
    Hu, Zhong-Yuan
    Du, Ding
    Tang, Wei-Fang
    Lu, Tao
    ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (05) : 2262 - 2264
  • [36] Chemoselective Cleavage and Transamidation of Tertiary p-Methoxybenzyl Amides under Metal-Free Photoredox Catalysis
    Jeong, Hee-Chan
    Lee, Hyo-Jun
    Maruoka, Keiji
    ORGANIC LETTERS, 2024, 26 (44) : 9513 - 9518
  • [37] Metal-free catalysis for the one-pot synthesis of organic carbamates from amines, CO2, and alcohol at mild conditions
    Zheng, Leizhi
    Yang, Guoqiang
    Liu, Jia
    Hu, Xingbang
    Zhang, Zhibing
    CHEMICAL ENGINEERING JOURNAL, 2021, 425
  • [38] Metal-Free One-Pot Oxidative Amidation of Aldoses with Functionalized Amines
    Colombeau, Ludovic
    Traore, Tenin
    Compain, Philippe
    Martin, Olivier R.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21): : 8647 - 8650
  • [39] Hypervalent iodine mediated C-H amination of quinoxalinones with heteroaromatic amines under metal-free conditions
    Qing-Qing Han
    De-Mao Chen
    Zu-Li Wang
    Yuan-Yuan Sun
    Shao-Hui Yang
    Jing-Cheng Song
    Dao-Qing Dong
    ChineseChemicalLetters, 2021, 32 (08) : 2559 - 2561
  • [40] Electrochemical strategies for N-cyanation of secondary amines and α C-cyanation of tertiary amines under transition metal-free conditions
    Fu, Zhengjiang
    Fu, Yaping
    Yin, Jian
    Hao, Guangguo
    Yi, Xuezheng
    Zhong, Tingting
    Guo, Shengmei
    Cai, Hu
    GREEN CHEMISTRY, 2021, 23 (23) : 9422 - 9427
12345