Malaysian Journal of Analytical Sciences Vol 21 No 5 (2017):
1203 - 1209
DOI:
https://doi.org/10.17576/mjas-2017-2105-25
ONE-POT MANNICH BASE SYNTHESIS
USING TASK SPECIFIC PROTIC IONIC LIQUIDS
(Sintesis
Bes Mannich Tunggal Menggunakan Cecair Ionik Terkhusus)
Sabahat
Sardar*, Cecilia Devi Wilfred, Jean Marc Leveque
Fundamental and Applied Sciences
Universiti Teknologi PETRONAS, Teronoh, Perak, Malaysia
*Corresponding author: sba.qau@gmail.com
Received: 21
August 2016; Accepted: 27 July 2017
Abstract
Three-component Mannich reaction of ketones, aromatic
aldehydes and aromatic amines was catalyzed by four Bronsted acidic ionic
liquids comprising of iodide and borate at room temperature. Ionic liquid have
been used as catalyst and solvent to produce some Mannich bases in high yield
(75%) and shorter reaction time (20 minutes). Work up has been facilitated by
simple extraction with water to recover ionic liquid for recycling up to four
times without any significant loss in activity.
Keywords: Mannich bases, Bronsted acidic ionic liquids, 1-methylimidazole, 1,3-propane sultone, 1,4-butane sultone
Abstrak
Tindak balas tiga komponen Mannich iaitu keton, aldehid
aromatik dan amina aromatik telah dimangkinkan oleh empat cecair ionik Bronsted
berasid yang terdiri daripada iodida dan borat pada suhu bilik. Cecair ionik
telah digunakan sebagai pemangkin dan pelarut untuk menghasilkan beberapa bes
Mannich dengan hasil yang tinggi (75%) dan masa tindak balas yang lebih pendek
(20 minit). Kerja pengekstrakan telah dipermudah dengan menggunakan air dan
boleh dikitar semula sehingga empat kali tanpa sebarang kehilangan aktiviti
yang penting.
Kata kunci: bes Mannich, asid Bronsted cecair ionik, 1-metilimidazol,
1,3-propana sulton, 1,4-butana sulton
References
1.
Mukhopadhyay, C., Rana, S. and Butcherb, R. J. (2010). An
ionic liquid {[secbmim]+Br-} as a “dual reagent catalyst”
for the multicomponent synthesis of (quinilinyl- and isoquinolinyl- amino)
alkylnaphthols, their bis- analogs and a facile route to naphthoxazines. ARKIVOC, 10: 291 – 304.
2.
Balasubramaniam, S. and Aidhen, I. S. (2008). The growing
synthetic utility of the weinreb amide, Synthesis,
2008(23): 3707 – 3738.
3.
Mogilaiah, K. and Kanksiah, G. (2002). Synthesis and
antibacterial activity of novel Mannich bases containing 1,8-naphthyridine
moiety. Indian Journal Heterocyclic
Chemistry, 11: 282 – 286.
4.
List, B. (2000). The direct catalytic asymmetric
three-component Mannich reaction. Journal
of American Chemical Society, 122: 9336 – 9338.
5.
Manabe, K., Mori, Y and Kobayashi, S. (2001). Three-component
carbon-carbon bond-forming reactions catalyzed by a Bronsted
acid-surfactant-combined catalyst in water. Tetrahedron,
57: 2537 – 2544.
6.
Kobayashi, S., Hamada, T. and Manabe, K. (2002). The
catalytic asymmetric Mannich type reactions in aqueous media. Journal of American Chemical Society, 124:
5640 – 5641.
7.
Zhao, G. and Lu, M. (2012). One-pot green procedure for
Mannich reaction catalyzed by task specific ionic liquid. Chiang Mai Journal of Science,
39: 49 – 58.
8.
Vadivel, P., Maheswari, C.
S. and Lalitha, A. (2013). Synthesis of β-amino carbonyl compounds via Mannich reaction
using sulfated MCM-41. International
Journal of Innovative Technology and Exploring Engineering, 2: 2278 – 3075.
9.
Hajipoura, A. R. and Rafieeb, F. (2009) Basic ionic liquids.
A short review. Journal of the Iranian
Chemical Society, 6: 647 – 678.
10.
Sahoo, S. Joseph, T. and Halligudi, S. B. (2006). Mannich
reaction in Bronsted acidic ionic liquids: A facile synthesis of β-amino
carbonyl compounds. Journal of Molecular
Catalysis A: Chemical, 244: 179 – 182.
11.
Cole, A. C. Jensen, J. L. Ntai, L. Loan, K. and Forbes, D. C.
(2002). Novel Bronsted acidic ionic liquids and their use as dual
solvent-catalyst. Journal of American
Chemical Society, 124: 5962 – 5963.
12.
Sapkal, S. B. Shelke, K. F. Madje, B. R. Shingate, B. B. and
Shingare, M. S. (2009). 1-butyl-3methyl imidazolium hydrogen sulphate promoted
one-pot three-component synthesis of amidoalskyl naphthols. Bulletin Korean Chemical Society, 30: 2887 – 2889.
13.
Rajendran, A. and Priyadarshini, M. (2010). Synthesis and
characterization of a novel ionic liquid (TBA-AMPS) and its applications in
Mannich condensation reactions under solvent free conditions. African
Journal of Pure and Applied Chemistry, 4: 183 – 187.
14.
Dyson, P. J. and Geldbach, T. J. (2007). Applications of
ionic liquids in synthesis and catalysis. The
Electrochemical Society Interface, 16(1): 50 – 53.
15.
Cserjesi, P., Bako K. B. and Gubicza, N. (2008). Recent
trends on application of ionic liquids in organic synthesis. Hungarian Journal of Industrial Chemistry,
36: 27 – 34.
16.
Rajendran, A., Ramu, S. and Karthikeyan, C. (2011). Green
synthesis of some novel N-Mannich bases using environmentally benign catalyst under
solvent free conditions. International
Journal of Current Research, 33: 161 – 167.
17.
Qain, H., Kai, W. and Zhen, J. (2016).
Ultrasound-promoted synthesis of β-amino carbonyl coumpounds via a Mannich reaction
catalyzed by ionic liquids. Letters in
Organic Chemistry, 13: 143 – 147.
18.
Senepak, W., Saeeng, R.,
Jaratiaroonphong, J., Kasemul, T. and Sirion, U. (2015). Green synthesis of
dipyyromethanes in aqueous media catalyzed by SO3H-funtionalized
ionic liquids. Organic & Biomolecular Chemistry, 14: 1302 – 1310.
19.
Kundamudi, K. Elavarasan, P. and Dyson, P. J (2010).
Alkylation of p-cresol with tert-butyl alcohol using benign Bronsted acidic
ionic liquid catalyst. Journal of Molecular
Catalysis, 321: 34 – 41.
20.
Han, X. and Zhou, L. (2011). Optimization of process
variables in the synthesis of butyl butyrate using acid ionic liquid as
catalyst. Journal of Chemical Engineering,
172: 459 – 466.
21.
Dubreuil, J. Bourahla, K. and Rahmouni, M. (2002). Catalyzed
esterifications in room temperature ionic liquids with acidic counteranion as
recyclable reaction media. Catalysis
Communications, 3: 185 – 190.
22.
Zahao, G., Jiang, T., Gao, H., Han, B., Haung, J. and Sun, D.
(2004). Mannich reaction using acidic ionic liquids as catalysts and solvents. Green Chemistry, 6(2): 75 – 77.
23.
Suryawanshi, N. S., Jain, P., Singhal M. and Khan, I. (2012).
Mannich synthesis under ionic liquid [Et3NH][HSO4] catalysis. IOSR Journal of Applied Chemistry 1: 18
– 23.
24.
Yang, Y. Y., Shou, W. G. and Wang, Y. G. (2006). Synthesis of
β–amino carbonyl compounds via a Zn(OTf)2-catalyzed cascade reaction
of anilines with aromatic aldehydes and carbonyl compounds. Tetrahedron, 62: 10079 – 10086.
25.
Fang, D., Fei, Z. and Liu, Z. L. (2009). Functionalized ionic
liquids as the recyclable catalyst for Mannich-type reaction in aqueous media. Catalysis Communications, 10: 1267 – 1270.
26.
Yi, L., Zou, J. H., Lei, H. S. and He, Q. L. (1991). The
Mannich reaction of butanone, aromatic aldehydes and aromatic amines. Synthetic Communications, 21: 2109 – 2117.
27.
Yi, W. B. and Cai,
C. (2006). Mannich-type reactions of aromatic aldehydes, anilines and methyl
ketones in fluorous biphase systems created by rare earth (III) perfluorooctane
sulfonates catalysts in fluorous media. Journal
of Fluorine Chemistry, 127: 1515 – 1521.