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

Year 2012, Volume: 1 Issue: 1, 23 - 44, 01.06.2012

Ahmed Alı Hullıo G.m Mastoı

https://izlik.org/JA34ME57MM

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. Sherman, A. R., “Pyridine” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.
• 2. http://en.wikipedia.org/wiki/Pyridine
• 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. (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. (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. Corey, E.J.; Suggs, W., Tetrahedron Lett., 1975, 16 (31), 2647-2650.
• 8. (a) http://tsch.en.alibaba.com/product/386185236-210551696/pyridine.html (b) http://chemicalland21.com/industrialchem/organic/PICOLINES.htm
• 10. http://www.inchem.org/documents/iarc/vol77/77-16.html.
• 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.
• 12. Hullio, A.A.; Mastoi, G.M., Oriental Journal of Chemistry, 2011, 27(4), 1591-1612
• 13. Jianzhou, G.; Youqu N. D.; Zhide, H.; Zhaolin,S. Tetrahedron lett., 2004, 45, 2681- 2683.
• 14. Liu, D.; Jianzhou, G.; Xiangqin, Z.; Lijuan, S.; Zhaolin, S.; Synth. Commun., 2007, 37, 759-765.
• 15. Xueling , M.; Sanzhong, L.; Cheng, J. P., J. Org. Chem., 2005, 70, 2338-2341.
• 16. Bukuo, Ni.; Zhang, Q.; Headley A. D.; Tetrahedron Lett., 2008, 49 (7), 1249-1252.
• 17. He, X.; Chan, T. H., Tetrahedron, 2006, 62 (14), 3389-3394.
• 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.
• 19. Sahoo, S.; Trissa, J.; Halligudi , S. B. Jr. of Mol. Cat. A: Chemical, 244, 179-182
• 20. Koguchi, S.; Kitazume, T. Tetrahedron Lett., 2006, 47(16), 2797-2801.
• 21. Hullio, A.A, Mastoi, G.M., Asian jr. of chem., 2011, 23(12) 5411-5418
• 22. Hullio, A.A, Mastoi, G.M., Iranian Jr. of Catal., 2011, 1(2), 79-86
• 23. Hullio, A.A, Mastoi, G.M., Chin. Jr. of chem., 2012, 7, 1647-1657
• 24. Handy, S. T. Chemistry - A Eur. Jr., 2003, 9(13), 2938–2944.
• 25. Hullio A.A, Mastoi G.M, Jordon Jr. of chem., 2012, 7(2), 125-138
• 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.
• 27. Diels, O.; Alder, K. Liebigs Ann. Chem. 1932, 498, 16-49.
• 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.
• 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.
• 30. Naira, V.; Devia, B. R.; Vidyaa, N.; Menona, R. S.; Abhilasha, N.; Nigam, P. R. Tetrahedron Lett., 2004, 45(16), 3203–3205.
• 31. Handy, S. T., A Eur. Jr of chem., 2003, 9(13), 2938.
• 32. M. Shibagaki , H. Matsushita , H. Kaneko, Heterocycles, 1983, 20, 497-500.
• 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.
• 34. Bonhote, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundaram, K.; Gratzel, M., Inorg. Chem., 1996, 35, 1168.
• 35. Nair, V.; Sreekanth, A. R.; Vinod, A. U., Org. Lett., 2001, 3 (22), 3495-3497.
• 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.
• 37. Acheson, R. M. Adv. Heterocycl. Chem. 1963, 1, 125.
• 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.
• 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.
• 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
• 41. De Souza, R. F.; Rech, V.; Dupont, J., Adv. Synth. Catal. 2002, 344, 153-155.
• 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.
• 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.