Nicotine-based ionic liquid: as a green catalyst for pyridine-catalyzed Huisgen reaction

محورهای موضوعی : Iranian Journal of Catalysis

Ahmed Ali Hullio ¹ (Dr. M.A Kazi Institute of chemistry, University of Sindh Jamshoro-76080, Pakistan.)
Ghulam Murtaza Mastoi ² (Dr. M.A Kazi Institute of chemistry, University of Sindh Jamshoro-76080, Pakistan.)

تاریخ دریافت : 1391/03/14 تاریخ پذیرش : 1391/10/03 تاریخ انتشار : 1391/09/11

کلید واژه: Pyridine, Nicotine-based ionic liquid, Pyridine-catalyzed Huisgen cycloaddition,

چکیده مقاله :

Nicotine-based ionic liquid has been used as a green catalyst for pyridine-catalyzed Huisgen reaction. It promoted addition of dimethylacetylenedicarboxylate to aldehydes or N-tosyl imines leading to efficient synthesis of 2-benzoylfumarates and 1-azadienes respectively under pyridine free odorless ionic liquid conditions. The improved results were obtained in terms of enhanced yields, with minimal work up.

منابع و مأخذ:

[1] (a) IARC Monogrpahs Vol. 77, OSHA, Washington D.C., 1985; (b) A.R. Sherman “Pyridine” in e-EROS (Encyclopedia of Reagents for Organic Synthesis) (Ed: L. Paquette) 2004, J. Wiley & Sons, New York, 2001; (c) D.J. Berry, C.V. Digiovanna, S.S. Metrick, R. Murugan, Arkivoc (2001) 201–226.
[2] (a) G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. Int. Ed. Engl. 17 (1978) 569-583; (b) R.P. Wurz, Chem. Rev., 107 (2007) 5570–5595.
[3] (a) S. Park, R.J. Kazlauskas, J. Org. Chem. 66 (2001) 8395-8401; (b) C. Chiappe, D. Pieraccini, J. Phys. Org. Chem. 18 (2005) 275-297.
[4] A.A. Hullio, G.M. Mastoi, Asian J. Chem. 23 (2011) 5411-5418.
[5] A.A. Hullio, G.M. Mastoi, Iran. J. Catal. 1 (2011) 79-86.
[6] A.A. Hullio, G.M. Mastoi, Chin. J. Chem. 7 (2012) 1647-1657.
[7] S.T. Handy, Chem. Eur. J. 9 (2003) 2938–2944.
[8] (a) A.A. Hullio, G.M. Mastoi, Jordon J. Chem. 7 (2012) 125-138; (b) A.A.Hullio, G.M. Mastoi, Stud. J. Chem. 1 (2012) 24-45.
[9] (a) R. Huisgen, J.G. Sauer, The Chemistry of Alkenes; S. Patai, Ed.; Wiley-Interscience, New York, 1964, 739-741; (b) R. Huisgen, K. Herbig, Liebigs Ann. Chem. 98 (1965) 688-692.
[10] O. Diels, K. Alder, Liebigs Ann. Chem. 498 (1932) 16-49.
[11] (a) R.M. Acheson, Adv. Heterocycl. Chem. 1 (1963) 125-126; (b) R.M. Acheson, G.A. Taylor, Proc. Chem. Soc. (1959) 186; (c) R.M. Acheson, G.A. Taylor, J. Chem. Soc. (1960) 1691-1701; (d) R.M. Acheson, A.O. Plunkett, J. Chem. Soc. (1964) 2676-2683.
[12] V. Nair, A.R. Sreekanth, N. Abhilash, A.T. Biju, B.R. Devi, R.S. Menon, N.P. Rath, R. Srinivas, Synthesis (2003) 1895-1902.
[13] V. Naira, B.R. Devia, N. Vidyaa, R.S. Menona, N. Abhilasha, P.R. Nigam, Tetrahedron Lett. 45 (2004) 3203–3205.