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.

 




Previous                    Content                    Next