Choline hydroxide promoted sustainable one-pot three-component synthesis of 1H-pyrazolo[1,2-a]pyridazine-2-carbonitriles under solvent-free conditions

被引:5
|
作者
Vajekar, Shailesh N. [1 ]
Shankarling, Ganapati S. [1 ]
机构
[1] Inst Chem Technol, Dept Dyestuff Technol, NP Marg, Mumbai 400019, Maharashtra, India
关键词
Choline hydroxide; 1H-pyrazolo[1; 2-a]pyridazine-2-carbonitrile; one-pot three-component; solvent-free; sustainable; IONIC LIQUID; MAGNETIC NANOCATALYST; HOMOGENEOUS CATALYST; EFFICIENT; ULTRASOUND; MALEIMIDE; MIXTURES; PROTOCOL; WATER;
D O I
10.1080/00397911.2020.1720736
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A sustainable one-pot three-component synthesis of novel 1H-pyrazolo[1,2-a]pyridazine-2-carbonitrile derivatives employing a highly efficient, biodegradable, and recyclable choline hydroxide catalyst under solvent-free conditions is demonstrated. The salient features of this protocol are simple workup, mild reaction conditions, short reaction time (10 min), excellent yields (up to 97%), high atom economy, column chromatography-free protocol, and eco-friendliness. Interestingly, the choline hydroxide was recycled up to five cycles without any considerable loss of efficiency. The structures of the products were deduced by their H-1 NMR, C-13 NMR, and HRLC-MS spectra.
引用
收藏
页码:1147 / 1158
页数:12
相关论文
共 50 条
  • [1] Facile synthesis of 1H-pyrazolo[1,2-a]pyridazine-5,8-dione derivatives by a one-pot, three-component reactions
    Teimouri, Mohammad Bagher
    Mansouri, Farideh
    Bazhrang, Reihaneh
    TETRAHEDRON, 2010, 66 (01) : 259 - 264
  • [2] Zinc Promoted One-Pot Three-Component Synthesis of 1,2-Diaryl Acetates under Solvent-Free Conditions
    Zhou, Pengxin
    Ren, Heng
    Wang, Kehu
    Wang, Jinxian
    Meng, Tuanjie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (09) : 1897 - 1903
  • [3] Facile Construction of 1H-Pyrazolo[1,2-a]pyridazine-5,8-diones via Acid-promoted One-pot Three-component Reaction
    Fatahpour, Maryam
    Hazeri, Nourallah
    Maghsoodlou, Malek Taher
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2020, 52 (03) : 238 - 241
  • [4] Synthesis of thiohydantoins under one-pot three-component solvent-free conditions
    Song Cao
    Longjie Zhu
    Chuanmeng Zhao
    Xiuhong Tang
    Huajun Sun
    Xin Feng
    Xuhong Qian
    Monatshefte für Chemie - Chemical Monthly, 2008, 139
  • [5] Synthesis of thiohydantoins under one-pot three-component solvent-free conditions
    Cao, Song
    Zhu, Longjie
    Zhao, Chuanmeng
    Tang, Xiuhong
    Sun, Huajun
    Feng, Xin
    Qian, Xuhong
    MONATSHEFTE FUR CHEMIE, 2008, 139 (08): : 923 - 926
  • [6] One-Pot Synthesis of Pyrimido[1,2-a]benzimidazoles under Solvent-Free Conditions
    Ghorbani-Vaghei, Ramin
    Toghraei-Semiromi, Zahra
    Karimi-Nami, Rahman
    Salimi, Zahra
    HELVETICA CHIMICA ACTA, 2014, 97 (07) : 979 - 984
  • [7] Solvent-free and efficient synthesis of imidazo[1,2-a]pyridine derivatives via a one-pot three-component reaction
    Wen, Li-Rong
    Li, Zhao-Rui
    Li, Ming
    Cao, Han
    GREEN CHEMISTRY, 2012, 14 (03) : 707 - 716
  • [8] One-pot synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-dione derivatives under solvent-free conditions
    Ghorbani-Vaghei, Ramin
    Noori, Samira
    Toghraei-Semiromi, Zahra
    Salimi, Zahra
    RSC ADVANCES, 2014, 4 (89) : 47925 - 47928
  • [9] Facile synthesis of imidazo[1,2-a]pyridines via a one-pot three-component reaction under solvent-free mechanochemical ball-milling conditions
    Maleki, Ali
    Javanshir, Shahrzad
    Naimabadi, Maryam
    RSC ADVANCES, 2014, 4 (57) : 30229 - 30232
  • [10] Efficient Synthesis of 1-Amidoalkyl-2-Naphthols by One-Pot, Three-Component Reaction under Solvent-Free conditions
    Karimi-Jaberi, Zahed
    Jokar, Marziyeh
    Abbasi, S. Zoleykha
    JOURNAL OF CHEMISTRY, 2013, 2013