Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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The First Report on Chemoselective Biguanide-Catalyzed Henry Reaction under Neat Conditions

  • Alizadeh, Abdolhamid (Department of Organic Chemistry, Faculty of Chemistry, Razi University) ;
  • Khodaei, Mohammad M. (Department of Organic Chemistry, Faculty of Chemistry, Razi University) ;
  • Abdi, Gisya (Department of Organic Chemistry, Faculty of Chemistry, Razi University) ;
  • Kordestani, Davood (Department of Organic Chemistry, Faculty of Chemistry, Razi University)
  • Received : 2012.05.23
  • Accepted : 2012.08.11
  • Published : 2012.11.20
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Abstract

An efficient synthetic method for direct Henry reaction catalyzed by a biguanide; namely metformin, as an organosuper-base, between a variety of aromatic and aliphatic aldehydes and nitromethane under neat conditions has been developed. Convenient procedure for removal of the catalyst, chemoselective acquiring of ${\beta}$-nitroalcohols as predominant products, as far as possible short reaction time with excellent conversions are advantages of the developed protocol.

Keywords

References

  1. Henry, L.; Seances, C. R. H. Acad. Sci. 1895, 120, 1265.
  2. Baer, H. H.; Urbas, L. The Chemistry of the Nitro and Nitroso Groups; Feuer, H., Ed.; Interscience: New York, 1970, Vol. 2.
  3. Rosini, G. In Comprehensive Organic Synthesis; Pergamon: New York, 1992; p 321.
  4. Luzzio, F. A. Tetrahedron 2001, 57, 915. https://doi.org/10.1016/S0040-4020(00)00965-0
  5. Torssell, K.; Zeuthen, O. Acta Chem. Scand. 1978, B32, 118.
  6. Bray, Ch. V.; Jiang, F.; Wu, X.; Sortais, J.; Darcel, Ch. Tetrahedron Lett. 2010, 51, 4555. https://doi.org/10.1016/j.tetlet.2010.06.106
  7. Zhou, C. L.; Zhou, Y. Q.; Wang, Z. Y. Chin. Chem. Lett. 2003, 14, 355.
  8. Ono, N.; Katayama, H.; Nishiyama, S.; Ogawa, T. J. Heterocyclic Chem. 1994, 31, 707. https://doi.org/10.1002/jhet.5570310402
  9. Ono, N.; Katayama, H.; Maruyama, K. Bull. Chem. Soc. Jpn. 1989, 62, 3386. https://doi.org/10.1246/bcsj.62.3386
  10. Ono, N.; Maruyama, K. Bull. Chem. Soc. Jpn. 1988, 61, 4470. https://doi.org/10.1246/bcsj.61.4470
  11. Simoni, D.; Invidiata, F. P.; Manfredini, S.; Ferroni, R. H.; Lampronti, I.; Roberti, M.; Pollini, G. P. Tetrahedron Lett. 1997, 38, 2749. https://doi.org/10.1016/S0040-4039(97)00461-9
  12. Herman, L. W.; ApSimon, J. W. Tetrahedron Lett. 1985, 26, 1423. https://doi.org/10.1016/S0040-4039(00)99061-0
  13. Ballini, R.; Bosica, G. J. Org. Chem. 1997, 62, 425. https://doi.org/10.1021/jo961201h
  14. Cavallo, A. S.; Lapitais, H.; Buchert, P.; Klein, A.; Colonna, S. J. Organomet. Chem. 1987, 330, 357. https://doi.org/10.1016/S0022-328X(00)99049-1
  15. Worrall, D. E. Org. Synth. 1941, 1, 413.
  16. Varma, R. S.; Dahiya, R.; Kumar, S. Tetrahedron Lett. 1997, 38, 5131. https://doi.org/10.1016/S0040-4039(97)01093-9
  17. Jenner, G. New J. Chem. 1999, 23, 525. https://doi.org/10.1039/a900899c
  18. Vaderbilt, B. M.; Hass, H. B. Ind. Eng. Chem. 1940, 32, 34. https://doi.org/10.1021/ie50361a007
  19. Hass, H. B.; Riley, E. F. Chem. Rev. 1943, 32, 373. https://doi.org/10.1021/cr60103a003
  20. Lichtenthaler, F. W. Angew. Chem., Int. Ed. Engl. 1964, 3, 211. https://doi.org/10.1002/anie.196402111
  21. Noland, W. E. Chem. Rev. 1955, 55, 137. https://doi.org/10.1021/cr50001a003
  22. Nielsen, A. T. The Chemistry of Functional Groups; Nitrones, Nitronates and Nitroxides; Patai, S., Rappoport, Z., Ed.; John Wiley & Sons; London, 1989.
  23. Ishikawa, T. The Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts; John Wiley & Sons: 2009.
  24. Han, J.; Xu, Y.; Su, Y.; She, X.; Pan, X. Catal. Commun. 2008, 9, 2077. https://doi.org/10.1016/j.catcom.2008.04.006
  25. Iwona, K.; Jerzy, R.; Zofia, U.; Janusz, J. Tetrahedron 2004, 60, 4807. https://doi.org/10.1016/j.tet.2004.04.005
  26. Simoni, D.; Rondanin, R.; Morini, M.; Baruchello, R.; Invidiata, F. P. Tetrahedron Lett. 2000, 41, 1607. https://doi.org/10.1016/S0040-4039(99)02340-0
  27. Raczynska, E. D.; Maria, P.-C.; Gal, J.-F.; Decouzon, M. J. Phys. Org. Chem. 1994, 7, 725. https://doi.org/10.1002/poc.610071211
  28. Ono, N. The Nitro Group in Organic Synthesis, ed. By John Wiley & Sons: London, 2001.
  29. Khan, F. A.; Dash, J.; Satapathy, R.; Upadhyay; S. K. Tetrahedron Lett. 2004, 45, 3055. https://doi.org/10.1016/j.tetlet.2004.02.103
  30. Jiang, T.; Gao, H.; Han, B.; Zhao, G.; Chang, Y.; Wu, W.; Gao, L.; Yang, G. Tetrahedron Lett. 2004, 45, 269. https://doi.org/10.1016/j.tetlet.2003.10.182
  31. Cwik, A.; Fuchs, A.; Hella, Z.; Clacens, J.-M. Tetrahedron 2005, 61, 4015. https://doi.org/10.1016/j.tet.2005.02.055
  32. Rodguez, J. M.; Pujol, D. M. Tetrahedron Lett. 2011, 52, 2629. https://doi.org/10.1016/j.tetlet.2011.03.037
  33. Karuthamohamed, D.; Jegathalaprathaban, R.; Ramanujam, K.; Gurusamy, R. Tetrahedron: Asymmetry 2011, 22, 857. https://doi.org/10.1016/j.tetasy.2011.04.020
  34. Zong-Liang, G.; Shi, Z.; Yong-Bo, L.; Gui, L. Tetrahedron: Asymmetry 2011, 22, 238. https://doi.org/10.1016/j.tetasy.2011.01.026
  35. Subba Reddy, B. V.; George, J. Tetrahedron: Asymmetry 2011, 22, 1169. https://doi.org/10.1016/j.tetasy.2011.06.012
  36. Nalluri, S.; Mariappan, P. Tetrahedron: Asymmetry 2009, 20, 1842. https://doi.org/10.1016/j.tetasy.2009.07.040
  37. Michail, N. E.; Alexey, I. I.; Valentina, M. M.; Fructuoso, B.; Belen, B. Tetrahedron 2008, 64, 5915. https://doi.org/10.1016/j.tet.2008.04.039
  38. Bing, Z.; Min, W.; Zhiyuan, L.; Qinghua, B.; Jianyou, M.; Shuoning, L.; Shangzhong, L.; Mingan, W.; Jiangchun, Z.; Hongchao, G. Tetrahedron: Asymmetry 2011, 22, 1156. https://doi.org/10.1016/j.tetasy.2011.06.032
  39. Xu-Guang, L.; Jia-Jun, J.; Min, S. B. Tetrahedron: Asymmetry 2007, 18, 2773. https://doi.org/10.1016/j.tetasy.2007.11.008
  40. Lai, G.; Wang, S.; Wang, Z. Tetrahedron: Asymmetry 2008, 19, 1813. https://doi.org/10.1016/j.tetasy.2008.06.036
  41. Basi, V. S. R.; Sankham, M. R.; Swain, M.; Chinnala, M. Tetrahedron: Asymmetry 2011, 22, 530. https://doi.org/10.1016/j.tetasy.2011.02.019

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