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

Abstract

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.

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

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.
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Details

Primary Language English
Journal Section Research Article
Authors

Ahmed Alı Hullıo This is me

G.m Mastoı This is me

Publication Date June 1, 2012
Published in Issue Year 2012 Volume: 1 Issue: 1

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