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Synthesis of 4-Alkylfuran-2-acetates and 4-Alkylthiophene-2-acetates Using 2-(Chloromethyl)-3-(tributylstannyl)propene

  • Kang, Kyung-Tae (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Hwang, Young-Back (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Kim, Mi-Young (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Lee, Seng-Kue (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University) ;
  • Lee, Jong-Gun (Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University)
  • Published : 2002.09.20
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References

  1. Marshall, J. A.; Wallace, E. M. J. Org. Chem. 1995, 60, 796. https://doi.org/10.1021/jo00109a007
  2. Mendez-Andino, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095 https://doi.org/10.1021/ol000325k
  3. Brown, T. H.; Armitage, M. A.; Blackmore, R. C.; Blutron, P.; Durant, G. J.; Ganellin, C. R.; Ife, R. G.; Parsons, M. E.; Rawlings, D. A.; Slingsby, B. P. Eur. J. Med. Chem. 1990, 25, 217. https://doi.org/10.1016/0223-5234(90)90204-G
  4. Sargent, M.; Cresp, T. M. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. P., Eds.; Pergamon Press: Oxford, 1979; vol. 4, pp 693-744.
  5. Lipshutz, B. H. Chem. Rev. 1986, 86, 795. https://doi.org/10.1021/cr00075a005
  6. Lee, C.-F.; Yang, L.-M.; Hou, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992 https://doi.org/10.1021/ja0004736
  7. Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955. https://doi.org/10.1016/S0040-4020(97)10303-9
  8. Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1999, 2849.
  9. Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 62, 8741.
  10. Bosshard, P.; Eugster, C. H. Adv. Heterocycl. Chem. 1966, 6, 378.
  11. Freidrichsen, W. Compr. Heterocycl. Chem. II 1996, 2, 351.
  12. Bures, E.; Spinazze, P. G.; Beese, G.; Hunt, I. R.; Regers, C.; Keay, B. A. J. Org. Chem. 1997, 62, 8741. https://doi.org/10.1021/jo971097j
  13. Sugawara, Y.; Kawai, H.; Matsmoto, T.; Okano, K.; Takizawa, S. Patent No. WO 9916763 (April 8, 1999).
  14. Carling, R. W.; Leeson, P. D. Synlett 1993, 40.
  15. Kang, K.-T.; U, J. S.; Hwang, S. S.; Jyung, K. K. Synth. Commun. 1994, 24, 2915. https://doi.org/10.1080/00397919408010613
  16. U, J. S.; Kang, K.-T. Bull. Korean Chem. Soc. 1994, 15, 1019.
  17. Kang, K.-T.; U, J. S. Synth. Commun. 1995, 25, 2647. https://doi.org/10.1080/00397919508011811
  18. Kim, E. K.; Lee, K. U.; Cho, B. Y.; Kim, Y. B.; Kang, K.-T. Liquid Crystals 2001, 28, 339. https://doi.org/10.1080/02678290010011599
  19. Kang, K.-T.; U, J. S.; Park, D. K.; Kim, J. G.; Kim, W. J. Bull. Korean Chem. Soc. 1995, 16, 464.
  20. Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954. https://doi.org/10.1021/ja00013a035
  21. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: London, 1987.
  22. Tamura, M.; Kochi, J. Synthesis 1971, 303.
  23. Volkmann, R. A.; Davis, J. T.; Meltz, C. N. J. Org. Chem. 1983, 48, 1767. https://doi.org/10.1021/jo00158a037
  24. Clemence, F.; Le Martret, O. GB 1331505 (Sep. 26, 1973).
  25. Cho, I.-S.; Muchowski, J. M. Synthesis 1991, 567.
  26. Baldwin, J. E.; Fieldhouse, R.; Russell, A. T. Tetrahedron Lett. 1993, 34, 5491. https://doi.org/10.1016/S0040-4039(00)73942-6

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