INVESTIGATION OF PYRIDINE-CATALYZED HUISGEN CYCLOADDITION REACTIONS IN NICOTINE-BASED TASK SPPECIFIC IONIC LIQUID

Abstract

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

References

1. 1. Sherman, A. R., “Pyridine” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
2. 2. http://en.wikipedia.org/wiki/Pyridine
3. 3. (a) IARC Monogrpahs Vol. 77, OSHA, Washington D.C., 1985; Sherman, A. R. “Pyridine” in e-EROS (Encyclopedia of Reagents for Organic Synthesis) (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. 2001. (b) Berry, D. J.; Digiovanna, C. V.; Metrick, S. S.; Murugan, R., Arkivoc, 2001, 201–226. (c) Höfle, G.; Steglich, W.; Vorbrüggen, H., Angew. Chem. Int. Ed. Engl., 1978, 17 (8), 569-583. (d) Wurz, R. P.; Chem. Rev., 2007, 107 (12), 5570–5595.
4. 4. (a) Sato, S.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. Tetrahedron, 2004, 60(36), 7899 -7906. (b) Bomann, M. D.; Guch, I. C.; DiMare, M., J. Org. Chem., 1995, 60, 5995-5996
5. 5. (a) Parikh, J. R.; Doering, W.V. E., J. Am. Chem. Soc., 1967, 89 (21): 5505–5507.(b) T.T Tidwell in L.A Paquette (ed:) Ecycopedia of Reagents for Organic Synthesis, John Wiley & Sons, 1995, 4703-4704.
6. 6. Corey, E.J.; Suggs, W., Tetrahedron Lett., 1975, 16 (31), 2647-2650.
7. 8. (a) http://tsch.en.alibaba.com/product/386185236-210551696/pyridine.html (b) http://chemicalland21.com/industrialchem/organic/PICOLINES.htm
8. 10. http://www.inchem.org/documents/iarc/vol77/77-16.html.

9. 11. (a) Park, S.; Kazlauskas, R. J., J. Org. Chem., 2001, 66, 8395-8401. (b) Chiappe, C.; Pieraccini, D., J. Phys. Org. Chem., 2005, 18, 275-297.
10. 12. Hullio, A.A.; Mastoi, G.M., Oriental Journal of Chemistry, 2011, 27(4), 1591-1612
11. 13. Jianzhou, G.; Youqu N. D.; Zhide, H.; Zhaolin,S. Tetrahedron lett., 2004, 45, 2681- 2683.
12. 14. Liu, D.; Jianzhou, G.; Xiangqin, Z.; Lijuan, S.; Zhaolin, S.; Synth. Commun., 2007, 37, 759-765.
13. 15. Xueling , M.; Sanzhong, L.; Cheng, J. P., J. Org. Chem., 2005, 70, 2338-2341.
14. 16. Bukuo, Ni.; Zhang, Q.; Headley A. D.; Tetrahedron Lett., 2008, 49 (7), 1249-1252.
15. 17. He, X.; Chan, T. H., Tetrahedron, 2006, 62 (14), 3389-3394.
16. 18. Yang, S. D.; Wu, L. Y. ; Yan, Z.Y.; Pan, Z. L. ; Liang, Y. M. ; Jr of Mol. Cat. A: 2007, 268(1-2), 107-111.
17. 19. Sahoo, S.; Trissa, J.; Halligudi , S. B. Jr. of Mol. Cat. A: Chemical, 244, 179-182
18. 20. Koguchi, S.; Kitazume, T. Tetrahedron Lett., 2006, 47(16), 2797-2801.
19. 21. Hullio, A.A, Mastoi, G.M., Asian jr. of chem., 2011, 23(12) 5411-5418
20. 22. Hullio, A.A, Mastoi, G.M., Iranian Jr. of Catal., 2011, 1(2), 79-86
21. 23. Hullio, A.A, Mastoi, G.M., Chin. Jr. of chem., 2012, 7, 1647-1657
22. 24. Handy, S. T. Chemistry - A Eur. Jr., 2003, 9(13), 2938–2944.
23. 25. Hullio A.A, Mastoi G.M, Jordon Jr. of chem., 2012, 7(2), 125-138
24. 26. (a) Huisgen, R.; Grashey; Sauer, J. The Chemistry of Alkenes; Patai, S., Ed.; WileyInterscience: New York, 1964; 739. (b) Huisgen, R.; Herbig, K. Liebigs Ann. Chem. 1965, 688, 98.
25. 27. Diels, O.; Alder, K. Liebigs Ann. Chem. 1932, 498, 16-49.
26. 28. (a) Acheson, R. M. Adv. Heterocycl. Chem. 1963, 1, 125. (b) Acheson, R. M.; Taylor, G. A. Proc. Chem. Soc. 1959, 186. (c) Acheson, R. M.; Taylor, G. A., J. Chem. Soc. 1960, 1691. (d) Acheson, R. M.; Plunkett, A. O., J. Chem. Soc. 1964, 2676.
27. 29. 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.
28. 30. Naira, V.; Devia, B. R.; Vidyaa, N.; Menona, R. S.; Abhilasha, N.; Nigam, P. R. Tetrahedron Lett., 2004, 45(16), 3203–3205.
29. 31. Handy, S. T., A Eur. Jr of chem., 2003, 9(13), 2938.
30. 32. M. Shibagaki , H. Matsushita , H. Kaneko, Heterocycles, 1983, 20, 497-500.
31. 33. (a) Gathergood, N.; Scammells, P. J., Aust. J. Chem., 2002, 55, 557; (b) Demberelnyamba, D.; Shin, B. K.; Lee, H., Chem. Commun., 2002, 1538.
32. 34. Bonhote, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundaram, K.; Gratzel, M., Inorg. Chem., 1996, 35, 1168.
33. 35. Nair, V.; Sreekanth, A. R.; Vinod, A. U., Org. Lett., 2001, 3 (22), 3495-3497.
34. 36. (a) Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019. (b) Nair, V.; Vinod, A. U.; Rajesh, C. J. Org. Chem. 2001, 66, 4427. (c) Nair, V.; Bindu, S.; Balagopal, L. Tetrahedron Lett. 2001, 42, 2043.
35. 37. Acheson, R. M. Adv. Heterocycl. Chem. 1963, 1, 125.
36. 38. (a) Acheson, R. M.; Taylor, G. A. Proc. Chem. Soc. 1959, 186. (b) Acheson, R. M.; Taylor, G. A. J. Chem. Soc. 1960, 1691.
37. 39. (a) Reviews: Winterfeldt, E., Angew. Chem., Int. Ed. Engl. 1967, 6, 423-434. (b) Acheson, R.M.; Elmore, N.F.; Adv. Heterocycl. Chem., 1978, 23, 263-483.
38. 40. (a) Nair, V.; Sreekanth, A.R.; Vinod, A.U.; Org. Lett., 2001, 3, 3495-3497. (b) V. Nair, A.R. Sreekanth and A.U. Vinod, Org. Lett., 2002, 4, 2807. (c) Nair, V.; Sreekanth, A.R.; Abhilash, N.; Biju, A.T.; Remadevi, B.; Menon, R.S.; Rath, N.P.; Srinivas, R., Synthesis, 2003, 1895-1902
39. 41. De Souza, R. F.; Rech, V.; Dupont, J., Adv. Synth. Catal. 2002, 344, 153-155.
40. 42. Handy, S. T.; Okello, M.; Dickenson, G.; Egrie, C. in Thirteenth International Symposium on Molten Salts (Eds.: P. Trulove, T. S. H. DeLong), Electochemical Society, Pennington, New Jersey, 2002.
41. 43. (a) Gathergood, N.; Scammells, P. J., Aust. J. Chem. 2002, 55, 557-5560 (b) Demberelnyamba, D.; Shin, B. K.; Lee, H. Chem. Commun. 2002, 1538-1539 (c) Branco, L. C.; Rosa, J. N.; Ramos, J. J. M.;. Afonso, C. A. M., Chem. Eur. J., 2002, 8, 3671-3677.