Acceleration under solvent-drop grinding: Synthesis of bis(indolyl) methanes using small amounts of organic solvents or ionic liquids

被引:10
作者
Tanemura, Kiyoshi [1 ]
机构
[1] Nippon Dent Univ, Sch Life Dent Niigata, Chem Lab, Hamaura, Niigata 9518580, Japan
关键词
Solvent-drop grinding; Solvent effect; Bis(indolyl)methanes; Ionic liquids; BIS-INDOLYL METHANE; SILICA-GEL; HETEROGENEOUS CATALYST; CONVENIENT SYNTHESIS; MICHAEL ADDITION; SOLID-STATE; EFFICIENT; ACID; WATER; CONDENSATION;
D O I
10.1016/j.tetlet.2021.153391
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions for the synthesis of bis(indolyl)methanes were accelerated by the addition of a few drops of solvents. Solvent effect for the addition of organic solvents and ionic liquids was examined. The yields of bis(indolyl)methanes increased by the addition of THF, 1-ethyl-3-ethylimidazolium bis(trifluoromethylsulfonyl)imide ([emim]NTf2), and 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim]PF6). Solvent-drop grinding methodology was quite useful for the reactions of "solid + liquid" as well as "solid + solid". (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:9
相关论文
共 76 条
[31]   Michael addition of indoles to β-nitrostyrenes catalyzed by HY zeolite under solvent-free conditions [J].
Jeganathan, Mariappan ;
Kanagaraj, Kuppusamy ;
Dhakshinamoorthy, Amarajothi ;
Pitchumani, Kasi .
TETRAHEDRON LETTERS, 2014, 55 (13) :2061-2064
[32]   Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions [J].
Jiang, Zhi-Jiang ;
Li, Zhen-Hua ;
Yu, Jing-Bo ;
Su, Wei-Ke .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (20) :10049-10055
[33]   SYNTHETIC APPROACHES FOR BIS (INDOLYL) METHANES [J].
Kaishap, Partha Pratim ;
Dohutia, Chandrajit .
INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2013, 4 (04) :1312-1322
[34]   A novel method for synthesis of cobalt manganese oxide nano catalysts as a recyclable catalyst for the synthesis of some bis (indolyl) methane derivatives [J].
Karami, Changiz ;
Ahmadian, Hossein ;
Nouri, Maryam ;
Jamshidi, Fariba ;
Mohammadi, Hadi ;
Ghodrati, Keivan ;
Farrokhi, Azita ;
Hamidi, Zohreh .
CATALYSIS COMMUNICATIONS, 2012, 27 :92-96
[35]   Polyvinylpolypyrrolidone-supported triflic acid (PVPP.OTf) as a new, efficient, and recyclable heterogeneous catalyst for the synthesis of bis-indolyl methane derivatives [J].
Khaksar, Samad ;
Tajbakhsh, Mahmoud ;
Gholami, Milad .
COMPTES RENDUS CHIMIE, 2014, 17 (01) :30-34
[36]   Olefin-accelerated solid-state C-N cross-coupling reactions using mechanochemistry [J].
Kubota, Koji ;
Seo, Tamae ;
Koide, Katsumasa ;
Hasegawa, Yasuchika ;
Ito, Hajime .
NATURE COMMUNICATIONS, 2019, 10 (1)
[37]   Asymmetric aldol condensation in an ionic liquid-water system catalyzed by (S)-prolinamide derivatives [J].
Kucherenko, A. S. ;
Syutkin, D. E. ;
Zlotin, S. G. .
RUSSIAN CHEMICAL BULLETIN, 2008, 57 (03) :591-594
[38]   Effect of External Electric Field and Temperature on Entropy, Heat of Capacity, and Chemical Reactivity with QSAR Study of Morphonium Chloride and Nitrous Ionic Liquids Crystal Using DFT [J].
Kumer, Ajoy ;
Islam, Mohammad Jahidul ;
Paul, Sunanda .
CHEMICAL METHODOLOGIES, 2020, 4 (05) :595-604
[39]   An Expeditious Green Cascade Synthesis of 3-Arylideneaminoquinazolin-4(1H)-one Derivatives via 'Solvent Drop Grinding' and Their Antioxidant and DNA Protective Studies [J].
Kuntikana, Sahana ;
Bhat, Chinmay ;
Kongot, Manasa ;
Bhat, Subrahmanya I. ;
Kumar, Amit .
CHEMISTRYSELECT, 2016, 1 (08) :1723-1728
[40]   Synthon polymorphs of 1: 1 co-crystal of 5-fluorouracil and 4-hydroxybenzoic acid: their relative stability and solvent polarity dependence of grinding outcomes [J].
Li, Song ;
Chen, Jia-Mei ;
Lu, Tong-Bu .
CRYSTENGCOMM, 2014, 16 (28) :6450-6458