Metal-free construction of aminated isoquinoline frameworks from 2-(2-oxo-2-arylethyl) benzonitrile in an aqueous medium

被引:3
|
作者
Sharma, Himanshi [1 ]
Kumar, Manoj [1 ]
Sethi, Aaftaab [1 ,2 ]
Poonam, Brijesh [3 ]
Rathi, Brijesh [1 ,2 ]
机构
[1] Univ Delhi, Hansraj Coll, Dept Chem, Delhi 110007, India
[2] Univ Delhi, Hansraj Coll, HeteroChem InnoTech, Delhi 110007, India
[3] Univ Delhi, Dept Chem, Miranda House, Delhi 110007, India
关键词
LONG-LIVED CATALYSTS; ARYLBORONIC ACIDS; IRIDIUM COMPLEXES; ARYL CHLORIDES; NITRILES; AMINES; 1-AMINOISOQUINOLINES; ACTIVATION; HETEROARYL; ADDITIONS;
D O I
10.1039/d2gc04044a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, we report a metal-free protocol for the activation of nitrile towards the nucleophilic addition and subsequent annulation under an aqueous medium for the first time. The protocol divulges an efficient route for the construction of diversified aminated isoquinolines. Differently substituted primary as well as secondary amines underwent the reaction in a highly regioselective manner. The reaction is operationally simple, shows high functional group tolerance, easier modification of well-known drugs, and successfully extended to gram-scale synthesis.
引用
收藏
页码:167 / 171
页数:5
相关论文
共 50 条
  • [41] Metal-Free Synthesis of 2-Arylbenzothiazoles from Aldehydes, Amines, and Thiocyanate
    Dey, Amrita
    Hajra, Alakananda
    ORGANIC LETTERS, 2019, 21 (06) : 1686 - 1689
  • [42] An efficient solvent-free synthesis of 2-(alkylamino)-2-oxo-1-arylethyl-6,12-dioxo-6,12-dihydroindolo[1,2-b]isoquinoline-11-carboxylate derivatives via four-component reaction
    Tahmineh Kenarkoohi
    Abbas Rahmati
    Molecular Diversity, 2019, 23 : 1011 - 1018
  • [43] An efficient solvent-free synthesis of 2-(alkylamino)-2-oxo-1-arylethyl-6,12-dioxo-6,12-dihydroindolo[1,2-b]isoquinoline-11-carboxylate derivatives via four-component reaction
    Kenarkoohi, Tahmineh
    Rahmati, Abbas
    MOLECULAR DIVERSITY, 2019, 23 (04) : 1011 - 1018
  • [44] Metal-free oxidative cyclization of 2-amino-benzamides, 2-aminobenzenesulfonamide or 2-(aminomethyl)anilines with primary alcohols for the synthesis of quinazolinones and their analogues
    Sun, Jinwei
    Tao, Tao
    Xu, Dan
    Cao, Hui
    Kong, Qinggang
    Wang, Xinyu
    Liu, Yun
    Zhao, Jianglin
    Wang, Yi
    Pan, Yi
    TETRAHEDRON LETTERS, 2018, 59 (21) : 2099 - 2102
  • [45] Metal-Free Oxidative Coupling: Xanthone Formation via Direct Annulation of 2-Aryloxybenzaldehyde using Tetrabutylammonium Bromide as a Promoter in Aqueous Medium
    Rao, Honghua
    Ma, Xinyi
    Liu, Qianzi
    Li, Zhongfeng
    Cao, Shengli
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2191 - 2196
  • [46] N-Rich 2D Heptazine Covalent Organic Frameworks as Efficient Metal-Free Photocatalysts
    Chen, Dan
    Chen, Weiben
    Zhang, Guang
    Li, Shen
    Chen, Weihua
    Xing, Guolong
    Chen, Long
    ACS CATALYSIS, 2022, 12 (01) : 616 - 623
  • [47] Metal-free catalysts for the hydrolysis of RNA derived from guanidines, 2-aminopyridines, and 2-aminobenzimidazoles
    Scheffer, U
    Strick, A
    Ludwig, V
    Peter, S
    Kalden, E
    Göbel, MW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) : 2211 - 2217
  • [48] Metal-free catalysts for the hydrolysis of RNA derived from guanidines, 2-aminopyridines, and 2-aminobenzimidazoles
    Scheffer, Ute
    Strick, Andreas
    Ludwig, Verena
    Peter, Sascha
    Kalden, Elisabeth
    Göbel, Michael W.
    Journal of the American Chemical Society, 1600, 127 (07): : 2211 - 2217
  • [49] Regulating π-Conjugation in sp2-Carbon-Linked Covalent Organic Frameworks for Efficient Metal-Free CO2 Photoreduction with H2O
    Yang, Lan
    Yan, Wenkai
    Yang, Na
    Wang, Guofeng
    Bi, Yingpu
    Tian, Chengcheng
    Liu, Honglai
    Zhu, Xiang
    SMALL, 2023, 19 (27)
  • [50] Metal-Free Synthesis of Pyrimidinone Derivatives via Biginelli Reaction Using Aqueous NaICl2
    Hatvate, Navnath T.
    Ghodse, Shrikant M.
    Mundlod, Krishna N.
    Telvekar, Vikas N.
    LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (08) : 613 - 617