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
来源：
GREEN CHEMISTRY | 2023年 / 25卷 / 01期
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
  • [21] Metal-free regioselective construction of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates
    Shi-Jing Zhai
    Dominique Cahard
    Fa-Guang Zhang
    Jun-An Ma
    Chinese Chemical Letters, 2022, 33 (02) : 863 - 866
  • [22] Metal-free regioselective construction of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates
    Zhai, Shi-Jing
    Cahard, Dominique
    Zhang, Fa-Guang
    Ma, Jun-An
    CHINESE CHEMICAL LETTERS, 2022, 33 (02) : 863 - 866
  • [23] Iodine(III)-Catalyzed Formal [2+2+1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles
    Yagyu, Takuma
    Takemoto, Yusuke
    Yoshimura, Akira
    Zhdankin, Viktor V.
    Saito, Akio
    ORGANIC LETTERS, 2017, 19 (10) : 2506 - 2509
  • [24] Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions
    Joseph, Devaneyan
    Park, Myeong Seong
    Lee, Sunwoo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (28) : 6227 - 6232
  • [25] Synthesis and characterization of new metal-free and metal phthalocyanines with peripheral N′-2-(cyanoethyl)aminoethylsulfanyl substituents
    Agirtas, MS
    Bekaroglu, Ö
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2001, 5 (10) : 717 - 720
  • [26] Metal-free I2O5-mediated direct construction of sulfonamides from thiols and amines
    Zhu, Minghui
    Wei, Wei
    Yang, Daoshan
    Cui, Huanhuan
    Wang, Leilei
    Meng, Guoqing
    Wang, Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (22) : 4789 - 4793
  • [27] A facile and efficient synthesis of β-amino alcohols using 2,2,2-trifluoroethanol as a metal-free and reusable medium
    Khaksar, Samad
    Heydari, Akbar
    Tajbaksh, Mahmood
    Bijanzadeh, Hamid Reza
    JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (01) : 106 - 110
  • [28] Simple and Efficient Large-scale Metal-free Synthesis of o-(5-Formyl-2-thienyl)benzonitrile and o-(5-Formyl-2-furyl)benzonitrile
    Lovric, Marija
    Tibi, Mohamed Majed
    Filipan, Mirela
    Cepanec, Ivica
    Litvic, Mladen
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2018, 50 (01) : 81 - 90
  • [29] The Ligand Free Palladium(II)-Catalyzed Regioselective 1,2-Addition of Enol Silanes to Quinones to Access 4-Hydroxy-4-(2-oxo-2-arylethyl)cyclohexadien-1-ones and Synthetic Applications
    Polimera, Subba Rao
    Subbaiah, Murugaiah A. M.
    Ilangovan, Andivelu
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 14356 - 14370
  • [30] Metal-free construction of dihydropyrazino[2,3-b]indoles from 2-aminoacetophenones, isocyanates and 1,2-diamines
    Fang, Jingxi
    Fang, Jiayao
    Rao, Yingbo
    Qiu, Huanyi
    Pan, Zhentao
    Ma, Yongmin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (10) : 2043 - 2048
12345