Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

RuCl2(PPh3)3-Catalyzed Facile One-Pot Synthesis of 1,2-Dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-ones and 1,2-Dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-thiones

  • Zhu, Xiaoyan (School of Chemical Engineering, Yeungnam University) ;
  • Lee, Yong Rok (School of Chemical Engineering, Yeungnam University)
  • Received : 2012.07.07
  • Accepted : 2012.08.01
  • Published : 2012.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Waxman, L.; Darke, P. L. Antiviral Chem. Chemother. 2000, 11, 1. https://doi.org/10.1177/095632020001100101
  2. Patel, M.; Ko, S. S.; McHugh, R. J., Jr.; Markwalder, J. A.; Srivastava, A. S.; Cordova, B. C.; Klabe, R. M.; Erickson- Vitanen, S.; Trainor, G. L.; Seitz, S. P.; Bioorg. Med. Chem. Lett. 1999, 9, 2805. https://doi.org/10.1016/S0960-894X(99)00486-2
  3. Patel, M.; McHugh, R. J., Jr.; Cordova, B. C.; Klabe, R. M.; Erickson-Vitanen, S.; Trainor, G. L.; Ko, S. S. Bioorg. Med. Chem. Lett. 1999, 9, 3221. https://doi.org/10.1016/S0960-894X(99)00565-X
  4. Klasek, A.; Koristek,K.; Polis, J.; Kosmrlj, J. Tetrahedron 2000, 56, 1551. https://doi.org/10.1016/S0040-4020(00)00057-0
  5. Kalluraya, B.; Sreenivasa, S. Farmaco 1998, 53, 399. https://doi.org/10.1016/S0014-827X(98)00037-8
  6. Larsen, R. D.; Corley, E. G.; King, A. O.; Carroll, J. D.; Davis, P.; Verhoeven, T. R.; Reider, P. J.; Labelle, M.; Gauthier, J. Y.; Xiang, Y. B.; Zamboni, R. J. J. Org. Chem. 1996, 61, 3398. https://doi.org/10.1021/jo952103j
  7. Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129. https://doi.org/10.1021/jm00040a003
  8. Chen, Y. L.; Fang, K. C.; Sheu, J. Y.; Hsu, S. L.; Tzeng, C. C. J. Med. Chem. 2001, 44, 2374. https://doi.org/10.1021/jm0100335
  9. Dube, D.; Blouin, M.; Brideau, C.; Chan, C. C.; Desmarais, S.; Ethier, D.; Falgueyret, J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Riendeau, D.; Tagari, P.; Young, R. N. Bioorg. Med. Chem. Lett. 1998, 8, 1255. https://doi.org/10.1016/S0960-894X(98)00201-7
  10. Iwahashi, M.; Kobayashi, K.; Nambu, F. Int. Patent Appl. WO 2003078409 A1, 2003.
  11. Vianello, P.; Bandiera, T. U.S. Patent Appl. US 20030073688 A1, 2003.
  12. Anderluh, M.; Cesar, J.; Stefanic, P.; Kikelj, D.; Janes, D.; Murn, J. Nadrah, K.; Tominc, M.; Addicks, E.; Giannis, A.; Stegnar, M.; Dolenc, M. S. Eur. J. Med. Chem. 2005, 40, 25. https://doi.org/10.1016/j.ejmech.2004.09.004
  13. Kajino, M.; Shibouta, Y.; Nishikawa, K.; Meguro, K. Chem. Pharm. Bull. 1991, 39, 2896. https://doi.org/10.1248/cpb.39.2896
  14. Gellibert, F. J.; Payne, A. H. Int. Patent Appl. WO 2003097639 A1, 2003.
  15. Nicolaiders, D. N.; Gautam, D. R.; Litinas, K. E.; Hadjipavlon-Litina, D. J.; Kontogiorgis, C. A. J. Heterocycl. Chem. 2004, 41, 605. https://doi.org/10.1002/jhet.5570410421
  16. Bethiel, R. S.; Ludeboer, M. U.S. Patent Appl. US 20040097504 A1, 2004.
  17. Kumar, A.; Saxena, A.; Dewan, M.; De, A.; Mozumdar, S. Tetrahedron Lett. 2011, 52, 4835. https://doi.org/10.1016/j.tetlet.2011.07.016
  18. Jiang, C.; Geng, X.; Zhang, Z.; Xu, H.; Wang, C. J. Chem. Res. 2010, 34, 19. https://doi.org/10.3184/030823409X12615635710356
  19. Ahangar, H. A.; Mahdavinia, G. H.; Marjani, K.; Hafezian, A. J. Iran. Chem. Soc. 2010, 7, 770. https://doi.org/10.1007/BF03246067
  20. Chaskar, A.; Vyavhare, V.; Padalkar, V.; Phatangare, K.; Deokar, H. J. Serb. Chem. Soc. 2011, 76, 21. https://doi.org/10.2298/JSC100410016C
  21. Kantevari, S.; Vuppalapati, S. V. N.; Bantu, R.; Nagarapu, L. J. Heterocycl. Chem. 2010, 47, 313.
  22. Nizam, A.; Päsha, M. A. Synth. Commun. 2010, 40, 2864. https://doi.org/10.1080/00397910903320654
  23. Terashima, T.; Ouchi, M.; Ando, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 2007, 40, 3581. https://doi.org/10.1021/ma062446r
  24. Paris, S. I. M.; Lemke, F. R. Inorg. Chem. Commun. 2005, 8, 425. https://doi.org/10.1016/j.inoche.2005.02.003
  25. Cho, C. S.; Kim, B. T.; Kim, H.-S.; Kim, T.-J.; Shim, S. C. Organometallics 2003, 22, 3608. https://doi.org/10.1021/om030307h
  26. Srivastava, V. K.; Shukla, R. S.; Bajaj, H. C.; Jasra, R. V. J. Mol. Catal. A-Chem. 2003, 202, 65. https://doi.org/10.1016/S1381-1169(03)00207-3
  27. Graban, E.; Lemke, F. R. Organometallics 2002, 21, 3823. https://doi.org/10.1021/om020271d
  28. Csjernyik, G.; Ell, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657. https://doi.org/10.1021/jo0163750
  29. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020. https://doi.org/10.1021/jo0108459
  30. Zhu, X.; Lee, Y. R.; Kim, S. H. Bull. Korean Chem. Soc. 2012, 33, 2799. https://doi.org/10.5012/bkcs.2012.33.8.2799
  31. Nagawade, R. R.; Shinde, D. B. Chin. J. Chem. 2007, 25, 1710. https://doi.org/10.1002/cjoc.200790316
  32. Das, B.; Kumar, D. N.; Laxminarayana, K.; Ravikanth, B. Helv. Chim. Acta 2007, 90, 1330. https://doi.org/10.1002/hlca.200790134
  33. Zhang, P.; Zhang, Z. H. Monatsh. Chem. 2009, 140, 199. https://doi.org/10.1007/s00706-008-0059-5
  34. Chavan, N. L.; Naik, P. N.; Nayak, S. K.; Kusurkar, R. S. Synth. Commun. 2010, 40, 2941. https://doi.org/10.1080/00397910903340702
  35. Rani, V. J.; Suresh, M.; Lavanya, P.; Vani, K. V.; Nagarjuna, B.; Rao, C. V. Der Pharma Chemica 2010, 6, 224.

Cited by

  1. nanoparticles and their novel catalytic applications for the synthesis of biologically interesting benzoxazinone and benzthioxazinone derivatives vol.38, pp.11, 2014, https://doi.org/10.1039/C4NJ01155D
  2. MgFe2O4@SiO2–SO3H: an efficient, reusable catalyst for the microwave-assisted synthesis of benzoxazinone and benzthioxazinone via multicomponent reaction under solvent free condition pp.1568-5675, 2018, https://doi.org/10.1007/s11164-017-3108-z
  3. A one-pot synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-ones catalyzed by iron(III) phosphate under solvent-free condition vol.47, pp.5, 2012, https://doi.org/10.1080/15533174.2016.1216452
  4. Graphene Oxide-Supported Ionic Liquid Phase Catalyzed Synthesis of 3,4-Dihydro-2H-naphtho[2,3-e][1,3]oxazine-5,10-diones vol.150, pp.1, 2012, https://doi.org/10.1007/s10562-019-02934-0