Task-specific ionic liquid incorporating anionic heteropolyacid-catalyzed Hantzsch and Mannich multicomponent reactions. Ionic liquid effect probed by ESI-MS(/MS)

被引：70
作者：
Alvim, Haline G. O. [1 ]
Bataglion, Giovana A. [2 ]
Ramos, Luciana M. [1 ]
de Oliveira, Aline L. [1 ]
de Oliveira, Heibbe C. B. [1 ]
Eberlin, Marcos N. [2 ]
de Macedo, Julio L. [3 ]
da Silva, Wender A. [4 ]
Neto, Brenno A. D. [1 ]
机构：
[1] Univ Brasilia IQ UnB, Lab Med & Technol Chem, BR-70904970 Brasilia, DF, Brazil
[2] Univ Estadual Campinas, UNICAMP, ThoMSon Mass Spectrometry Lab, BR-13085970 Campinas, SP, Brazil
[3] Univ Brasilia, Inst Chem, Catalysis Lab, BR-70904970 Brasilia, DF, Brazil
[4] Univ Brasilia IQ UnB, Lab Bioact Cpds Synth, BR-70904970 Brasilia, DF, Brazil
来源：
TETRAHEDRON | 2014年 / 70卷 / 20期
基金：
巴西圣保罗研究基金会;
关键词：
Ionic liquids; Multicomponent reactions; Mechanism; ESI-MS; Bioactive; IONIZATION MASS-SPECTROMETRY; N-ACYLIMINIUM IONS; BIGINELLI REACTION; GAS-PHASE; ORGANIC-SYNTHESIS; PERFECT SYNERGY; MOLTEN-SALTS; CHEMISTRY; GREEN; SOLVENTS;
D O I：
10.1016/j.tet.2013.10.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A task-specific ionic liquid with a Bronsted acid (1-(3-sulfopropyI)-3-methylimidazolium hydrogen sulfate, namely MSI) bearing an anionic heteropolyacid derivative ([PW12O40](3-), namely PW) were used as an efficient catalyst for the three-component Mannich and Hantzsch reactions. Using (MSI)(3)PW as the catalyst supported in imidazolium-based ionic liquids allowed these multicomponent reactions to take place in good to excellent yields. The Mannich reaction, performed at room temperature, was also evaluated by means of electrospray (tandem) mass spectrometry ESI-MS(/MS). ESI-MS data pointed to the origin of the ionic liquid effect, i.e., formation of ion pairs with the charged reaction intermediates and furthers association into larger supramolecular aggregates. DFT calculations revealed the strength of the supramolecular interactions between the charged species detected by ESI-MS and the spontaneity association of these ion pairs affording larger supramolecular aggregates. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3306 / 3313
页数：8
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