Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Methyl (E)-2-Cyanomethylcinnamates Derived from Baylis-Hillman Acetates and Conversion into Several 4-Hydroxy-2-naphthoic Acids and Benzylidenesuccinimides

  • Hong, Wan-Pyo (Department of Chemical Engineering, Hanyang University) ;
  • Lim, Hee-Nam (Department of Chemical Engineering, Hanyang University) ;
  • Park, Hong-Woo (Department of Chemical Engineering, Hanyang University) ;
  • Lee, Kee-Jung (Department of Chemical Engineering, Hanyang University)
  • Published : 2005.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653 https://doi.org/10.1016/S0040-4020(01)86168-8
  2. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001 https://doi.org/10.1016/0040-4020(96)00154-8
  3. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201
  4. Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049 https://doi.org/10.1002/1521-3773(20000901)39:17<3049::AID-ANIE3049>3.0.CO;2-5
  5. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627 https://doi.org/10.2174/1385272023374094
  6. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811 https://doi.org/10.1021/cr010043d
  7. Genski, T.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43, 3573 https://doi.org/10.1016/S0040-4039(02)00529-4
  8. Sammelson, R. E.; Gurusinghe, C. D.; Kurth, J. M.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 2002, 67, 86 https://doi.org/10.1021/jo010579z
  9. Ciclosi, M.; Fava, C.; Galeazzi, R.; Orena, M.; Sepulveda-Arques, J. Tetrahedron Lett. 2002, 43, 2119 https://doi.org/10.1016/S0040-4039(02)00198-3
  10. Song, Y. S.; Lee, C. H.; Lee, K.-J. J. Heterocyclic Chem. 2003, 40, 939
  11. Lee, C. H.; Song, Y. S.; Cho, H. I.; Yang, J. W.; Lee, K.-J. J. Heterocyclic Chem. 2003, 40, 1103
  12. Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron 2002, 58, 3693 https://doi.org/10.1016/S0040-4020(02)00332-0
  13. Basavaiah, D.; Satyanarayana, T. Tetrahedron Lett. 2002, 43, 4301 https://doi.org/10.1016/S0040-4039(02)00802-X
  14. Kaye, P. T.; Nocanda, X. W. J. Chem. Soc., Perkin Trans. 1 2002, 1318
  15. Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341 https://doi.org/10.1016/S0040-4039(01)01791-9
  16. Kaye, P. T.; Nocanda, X. W. J. Chem. Soc., Perkin Trans. 1 2000, 1331
  17. Basavaiah, D.; Sreenivasulu, B.; Rao, J. S. Tetrahedron Lett. 2001, 42, 1147 https://doi.org/10.1016/S0040-4039(00)02175-4
  18. Alcaide, B.; Almendros, P.; Aragoncillo, C. Tetrahedron Lett. 1999, 40, 7537 https://doi.org/10.1016/S0040-4039(99)01527-0
  19. Franck, X.; Figadere, B. Tetrahedron Lett. 2002, 43, 1449 https://doi.org/10.1016/S0040-4039(02)00058-8
  20. Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867 https://doi.org/10.1016/S0040-4039(01)01676-8
  21. Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030
  22. Mateus, C. R.; Feltrin, M. P.; Costa, A. M.; Coelho, F.; Almeida, W. P.; Jauch, J. Synlett 2001, 87
  23. Reiser, U.; Jauch, J. Synlett 2001, 90
  24. Jauch, J. Angew. Chem. Int. Ed. 2000, 39, 2764 https://doi.org/10.1002/1521-3773(20000804)39:15<2764::AID-ANIE2764>3.0.CO;2-S
  25. Fleming, F. F.; Zhang, Z. Tetrahedron 2005, 61, 747 https://doi.org/10.1016/j.tet.2004.11.012
  26. Kim, J. N.; Lee, H. J.; Lee, K. Y.; Gong, J. H. Synlett 2002, 173
  27. Kim, J. N.; Lee, H. J.; Lee, K. Y.; Kim, H. S. Tetrahedron Lett. 2001, 42, 3737 https://doi.org/10.1016/S0040-4039(01)00552-4
  28. Basavaiah, D.; Kumaragurubaran, N. Tetrahedron Lett. 2001, 42, 477 https://doi.org/10.1016/S0040-4039(00)01967-5
  29. Im, Y. J.; Kim, J. M.; Mun, J. H.; Kim, J. N. Bull. Korean Chem. Soc. 2001, 22, 349
  30. Drewes, S. E.; Horn, M. M.; Ramesar, N. Synth. Commun. 2000, 30, 1045 https://doi.org/10.1080/00397910008087122
  31. Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr. 1989, 403
  32. Basavaiah, D.; Pandiaraju, S. Tetrahedron 1996, 52, 2261 https://doi.org/10.1016/0040-4020(95)01055-6
  33. Patra, A.; Roy, A. K.; Batra, S.; Bhaduri, A. P. Synlett 2002, 1819
  34. Kim, J. N.; Im, Y. J.; Gong, J. H.; Lee, K. Y. Tetrahedron Lett. 2001, 42, 4195 https://doi.org/10.1016/S0040-4039(01)00687-6
  35. Kim, J. M.; Im, Y. J.; Kim, T. H.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 657 https://doi.org/10.5012/bkcs.2002.23.5.657
  36. Basavaiah, D.; Hyma, R. S.; Kumaragurubaran, N. Tetrahedron 2000, 56, 5905 https://doi.org/10.1016/S0040-4020(00)00478-6
  37. Chung, Y. M.; Gong, J. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2001, 41, 9023
  38. Almeida, W. P.; Coelho, F. Tetrahedron Lett. 1998, 39, 8609 https://doi.org/10.1016/S0040-4039(98)01927-3
  39. Hong, W. P.; Lee, K.-J. Synthesis 2005, 33
  40. Lee, C. H.; Lee, K.-J. Synthesis 2004, 1941
  41. Park, J. B.; Ko, S. H.; Kim, B. G.; Hong, W. P.; Lee, K.-J. Bull. Korean Chem. Soc. 2004, 25, 27 https://doi.org/10.5012/bkcs.2004.25.1.027
  42. Park, J. B.; Ko, S. H.; Hong, W. P.; Lee, K.-J. Bull. Korean Chem. Soc. 2004, 25, 927 https://doi.org/10.5012/bkcs.2004.25.6.927
  43. Cason, J. J. Am. Chem. Soc. 1941, 63, 828 https://doi.org/10.1021/ja01848a054
  44. El-Abbady, A. M.; Doss, S. H.; Moussa, H. H.; Nosseir, M. J. Org. Chem. 1961, 26, 4871 https://doi.org/10.1021/jo01070a021
  45. House, H. O.; Larson, J. K. J. Org. Chem. 1968, 33, 448 https://doi.org/10.1021/jo01265a105
  46. Hedaya, E.; Theodoropulos, S. Tetrahedron 1968, 24, 2241 https://doi.org/10.1016/0040-4020(68)88126-8
  47. Stobbe, H. Ber. 1893, 26, 2312 https://doi.org/10.1002/cber.18930260306
  48. Johnson, W. S.; Daub, G. H. In Organic Reactions, Vol. 6; Adams, R., Ed.; Wiley; New York, 1951; p 1
  49. Wang, S.; Pan, J.; Hu, Y.; Hu, H. Synthesis 2005, 753
  50. Jendralla, H.; Henning, R.; Seuring, B.; Herchen, J.; Kulitzscher, B.; Wunner, J. Synlett 1993, 155
  51. Mathur, K. B. L.; Krishnamurti, M.; Pandit, U. K. J. Am. Chem. Soc. 1953, 75, 3240 https://doi.org/10.1021/ja01109a057
  52. Vul'fson, N. S.; Zhurina, F. G.; Senyavina, L. B. Zh. Org. Khim. 1967, 3, 341
  53. Vul'fson, N. S.; Zhurina, F. G.; Senyavina, L. B. Chem. Abstr. 1967, 66, 115428
  54. Bryant, D. R.; Hauser, C. R. J. Am. Chem. Soc. 1961, 83, 3468 https://doi.org/10.1021/ja01477a028

Cited by

  1. Using Morita-Baylis-Hillman acetates of 2-azidobenzaldehydes for the synthesis of 2-alkoxy-3-cyanomethylquinolines and alkyl quinoline-3-carboxylates vol.48, pp.4, 2011, https://doi.org/10.1002/jhet.667
  2. Morita-Baylis-Hillman Route to Dimethyl 2,3-Dihydrobenzo[b]oxepine-2,4-dicarboxylates and Methyl 2-(2-Carbomethoxybenzo[b]furan-3-yl)propanoates from Salicylaldehydes vol.33, pp.1, 2012, https://doi.org/10.5012/bkcs.2012.33.1.233
  3. Elegant Synthesis of Highly Functionalized 1,2,3-Trisubstituted Cyclopentanes vol.43, pp.11, 2013, https://doi.org/10.1080/00397911.2011.654371
  4. 2′-Intramolecular Oxidative Nucleophilic Substitution of Hydrogen-E2 Elimination vol.37, pp.6, 2016, https://doi.org/10.1002/bkcs.10774
  5. Simple and facile synthesis of tetralone-spiro-glutarimides and spiro-bisglutarimides from Baylis–Hillman acetates vol.6, pp.6, 2008, https://doi.org/10.1039/b717843c
  6. ]oxepine-4-carboxylates vol.45, pp.6, 2008, https://doi.org/10.1002/jhet.5570450622
  7. Synthesis of Methyl (E)-2-Cyanomethylcinnamates (III) Derived from Baylis—Hillman Acetates (I) and Conversion into Several 4-Hydroxy-2-naphthoic Acids (V) and Benzylidenesuccinimides (VI). vol.36, pp.37, 2005, https://doi.org/10.1002/chin.200537078
  8. The First Synthesis of 3,5-Dimethylene-4-phenylpiperidine-2,6-dione from Baylis-Hillman Adduct vol.27, pp.1, 2005, https://doi.org/10.5012/bkcs.2006.27.1.140
  9. Advances in the Baylis-Hillman reaction-assisted synthesis of cyclic frameworks vol.64, pp.20, 2008, https://doi.org/10.1016/j.tet.2008.02.087
  10. Quinolines from Morita–Baylis–Hillman acetates of 2-azidobenzaldehydes vol.65, pp.46, 2005, https://doi.org/10.1016/j.tet.2009.09.047
  11. Morita.Baylis.Hillman Route to 8,9,9a,10-Tetrahydrobenzo[b][1,8]naphthyridine-6(7H)-ones and 3,4,4a,5-Tetrahydrodibenzo[b,g][1,8]naphthyridine-1(2H)-ones vol.32, pp.8, 2005, https://doi.org/10.5012/bkcs.2011.32.8.3145