Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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New One-Pot Synthesis of 4-Hydroxybenzaldehyde Derivatives and Picric Acid from 4-Hydroxyphenylglycine with HNO3/H2O

  • Shin, Young-Gyun (Department of Molecular Science and Technology, Ajou University) ;
  • Yoon, Sung-Hwa (Department of Molecular Science and Technology, Ajou University)
  • Published : 2009.11.20
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References

  1. Olah, G. A.; Kuhn, S. J. J. Am. Chem. Soc. 1960, 82, 2380 https://doi.org/10.1021/ja01494a065
  2. Rieche, A.; Gross, H.; H$\ddot{o}$ft, E. Chem. Ber. 1960, 93, 88 https://doi.org/10.1002/cber.19600930115
  3. Youssefyeh, R. D. Tetrahedron lett. 1964, 32, 2161
  4. Tanaka, M.; Fujiwara, M.; Ando, H. J. Org. Chem. 1995, 60, 2106 https://doi.org/10.1021/jo00112a035
  5. Olah, G. A.; Laali, K.; Farooq, O. J. Org. Chem. 1985, 50, 1483 https://doi.org/10.1021/jo00209a025
  6. Lee, D. G.; Spitzer, U. A. J. Org. Chem. 1970, 35, 3589. https://doi.org/10.1021/jo00835a101
  7. Rao, Y. S.; Filler, R. J. Org. Chem. 1974, 39, 3589 https://doi.org/10.1080/00397919708007291
  8. Lou, J. D.; Lu, L. H.; Liu, W. Synth.Commun. 1997, 27, 3701 https://doi.org/10.1080/00397919708007291
  9. Khadilka, B.; Chitnavis, A.; Khare, A. Synth.Commun. 1996, 26 https://doi.org/10.1021/jo9609790
  10. Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J. L. J. Org. Chem. 1996, 61, 7452 https://doi.org/10.1021/ja973227b
  11. Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. https://doi.org/10.1016/S0040-4039(00)61180-2
  12. Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977
  13. Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029 https://doi.org/10.1016/S0040-4039(00)61180-2
  14. Jian, Z.; Wang, Z.; Wu, Y. Huaxue Gongye Yu Gongcheng Jishu 2005, 26(1), 5. https://doi.org/10.1039/b307186c
  15. Jian, Z.; Wang, Z.; Wu, Y. Jingxi Huagong Zhongjianti 2005, 35(1), 50. https://doi.org/10.1021/ja01302a046
  16. Woodburn, H. M.; Lathroum, L. B. J. Org. Chem. 1954, 19, 285. https://doi.org/10.1021/jo01368a001
  17. Engel, P.; Paradisi, F.; McCrohan, O.; Maguire, A.; Collins, S. G.; Busca, P.; Giacomini, D. Patent WO2006015885.
  18. Chen, Y. T.; Seto, C. T. J. Med. Chem. 2002, 45, 3946. https://doi.org/10.1021/jm020093q
  19. Kanzaki, H.; Isobe, A.; Izumi, Y.; Yamada, H. Agric. Biol. Chem. 1990, 54(8), 2101. https://doi.org/10.1271/bbb1961.54.2101
  20. Kondo, H.; Tanamachi, H.; Sunamoto, J. Chem. Lett. 1988, 12, 2013.
  21. Garcia-Raso, A.; Deya, P. M.; Saa, J. M. J. Org. Chem. 1986, 51, 4285. https://doi.org/10.1021/jo00372a033
  22. Park, J. K.; Jung, J. Y. Enzyme. Microb. Tech. 2002, 30(6), 726. https://doi.org/10.1016/S0141-0229(02)00049-2
  23. D'Auria, M.; Distefano, C.; D'Onofrio, F.; Mauriello, G.; Racioppi, R. J. Chem. Soc. Perkin 1 2000, 20, 3513.
  24. Craig, J. C.; Ekwuribe, N. N. Synthesis 1980, 11, 909.
  25. Cohen, T.; Song, I. H. J. Am. Chem. Soc. 1965, 87(16), 3780. https://doi.org/10.1021/ja01094a049
  26. Itoh, S.; Kato, N.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1984, 25(42), 4753 https://doi.org/10.1016/S0040-4039(01)81510-0
  27. Hendel, W.; Heu, F.; Poechlauer, P.; Winkler, B. U. S. Patent 2003045725.
  28. Hendel, W.; Heu, F.; Poechlauer, P.; Winkler, B. U. S. Patent 2003144558.
  29. Favier, I.; Dunach, E.; Hebrault, D.; Desmurs, J. R. New. J. Chem. 2004, 28, 62 https://doi.org/10.1039/b307186c
  30. Herbst, R. M. J. Am. Chem. Soc. 1936, 58, 2239 https://doi.org/10.1021/ja01302a046
  31. March, J.; Smith, M. B. MARCH's Advanced Organic Chemistry; Wiley: NY, 2001; p 696
  32. Budavari, S. The Merck Index, 17th Ed.; Merck & Co., Inc.: 1997

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