Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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AgBF4/[Bmim]BF4-Catalyzed [3+2] Cycloaddition of Cyclic Diazodicarbonyl Compounds: Efficient Synthesis of 2,3-Dihydrofurans and Conversion to 3-Acylfurans

  • Xia, Likai (School of Chemical Engineering, Yeungnam University) ;
  • Lee, Yong-Rok (School of Chemical Engineering, Yeungnam University) ;
  • Kim, Sung-Hong (Analysis Research Division, Daegu Center, Korea Basic Science Institute) ;
  • Lyoo, Won-Seok (School of Textiles, Yeungnam University)
  • Received : 2011.03.16
  • Accepted : 2011.03.18
  • Published : 2011.05.20
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Abstract

A novel and efficient method for the synthesis of 2,3-dihydrofurans bearing a variety of substituents on the dihydrofuran ring was achieved by the reaction of cyclic diazodicarbonyl compounds with styrene and vinyl acetate. The key strategy was AgBF$_4$/[Bmim]BF$_4$-catalyzed [3+2] cycloaddition. The synthesized dihydrofurans with an acetate group were further converted to the corresponding 3-acylfurans.

Keywords

References

  1. Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, 1982; Vol. 30, pp 167-238.
  2. Dean, F. M.; Sargent, M. V. In Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon: New York, 1984; Vol. 4, part 3, pp 531-598.
  3. Lipshutz, B. H. Chem. Rev. 1986, 86, 795-820. https://doi.org/10.1021/cr00075a005
  4. Nakanishi, K. In Natural Products Chemistry; Kodansha: Tokyo, 1974.
  5. The Chemistry of Heterocyclic Flavoring and Aroma Compounds, Vernin, G., Ed.; Ellis Horwood: Chichester, 1982.
  6. Kubo, I.; Lee, Y. W.; Balogh-Nair, V.; Nakanishi, K.; Chapya, A. J. Chem. Soc., Chem. Commun. 1976, 949-850.
  7. Schulte, G.; Scheuer, P. J.; McConnell, O. J. Helv. Chim. Acta 1980, 63, 2159-2167. https://doi.org/10.1002/hlca.19800630805
  8. Maharramov, A. M.; Sadikhova, N. D.; Mammadov, I. G.; Allahverdiyev, M. A. Chem. Heterocycl. Compd. 2009, 45, 400- 404. https://doi.org/10.1007/s10593-009-0293-8
  9. Wang, Q.; Hou, H.; Hui, L.; Yan, C. J. Org. Chem. 2009, 74, 7403-7406. https://doi.org/10.1021/jo901379h
  10. Karade, N. N.; Shirodkar, S. G.; Patil, M. N.; Potrekar, R. A.; Karade, H. N. Tetrahedron Lett. 2003, 44, 6729- 6731. https://doi.org/10.1016/S0040-4039(03)01644-7
  11. Aso, M.; Ojida, A.; Yang, G.; Cha, O. J.; Osawa, E.; Kanematsu, K. J. Org. Chem. 1993, 58, 3960-3968. https://doi.org/10.1021/jo00067a031
  12. Ferreira, S. B.; Kaiser, C. R.; Ferreira, V. F. Org. Prep. Proced. Int. 2009, 41, 211-215. https://doi.org/10.1080/00304940902955855
  13. Ali, M. F.; Calskan, R.; Pahin, E.; Balci, M. Tetrahedron 2009, 65, 1430-1437. https://doi.org/10.1016/j.tet.2008.12.012
  14. Savitha, G.; Sudhakar, R.; Perumal, P. T. Tetrahedron Lett. 2008, 49, 7260- 7263. https://doi.org/10.1016/j.tetlet.2008.10.011
  15. Ranu, B. C.; Adak, L.; Banerjee, S. Tetrahedron Lett. 2008, 49, 4613-4617. https://doi.org/10.1016/j.tetlet.2008.05.083
  16. Ceylan, M.; Findik, E. Synth. Commun. 2008, 38, 1070-1077. https://doi.org/10.1080/00397910701862782
  17. Tanimori, S.; Kato, Y.; Kirihata, M. Synthesis 2006, 865-869.
  18. Grigg, R.; Kongathip, N.; Kongathip, B.; Luangkamin, S.; Dondas, H. A. Tetrahedron 2001, 57, 9187- 9197. https://doi.org/10.1016/S0040-4020(01)00924-3
  19. Chen, F.-E.; Fu, H.; Meng, G.; Cheng, Y.; Hu, Y.-L. Synthesis 2000, 1091-1094.
  20. Asouti, A.; Hadjiarapoglou, L. P. Tetrahedron Lett. 1998, 39, 9073-9076. https://doi.org/10.1016/S0040-4039(98)01997-2
  21. Alexiou, I.; Gogonas, E. P.; Hadjiarapoglou, L. P. Synlett 1999, 12, 1925-1926.
  22. Nair, V.; Mathew, J.; Radhakrishnan, K. V. J. Chem. Soc., Perkin Trans. 1 1996, 1487-1492.
  23. Iqbal, J.; Bhatia, B.; Nayyar, N. K. Tetrahedron 1991, 47, 6457-6468. https://doi.org/10.1016/S0040-4020(01)86573-X
  24. Lee, Y. R.; Hwang, J. C. Eur. J. Org. Chem. 2005, 1568-1577.
  25. Lee, Y. R.; Suk, J. Y. Tetrahedron 2002, 58, 2359-2367. https://doi.org/10.1016/S0040-4020(02)00118-7
  26. Lee, Y. R.; Suk, J. Y. Tetrahedron Lett. 2000, 41, 4795-4799. https://doi.org/10.1016/S0040-4039(00)00716-4
  27. Lee, Y. R. Synth. Commun. 1998, 28, 865-869. https://doi.org/10.1080/00032719808006485
  28. Lee, Y. R.; Suk, J. Y. Heterocycles 1998, 48, 875-883. https://doi.org/10.3987/COM-97-7881
  29. Lee, Y. R.; Morehead, A. T., Jr. Tetrahedron 1995, 51, 4909-4922. https://doi.org/10.1016/0040-4020(95)98689-F
  30. Mueller, P.; Allenbach, Y. F.; Ferri, M.; Bernardinelli, G. ARKIVOC 2003, 80-95.
  31. Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1-326.
  32. Ishitani, H.; Achiwa, K. Heterocycles 1997, 46, 153-156. https://doi.org/10.3987/COM-97-S54
  33. Oh, C. H.; Karmakar, S.; Park, H. S.; Ahn, Y. C.; Kim, J. W. J. Am. Chem. Soc. 2010, 132, 1792-1793. https://doi.org/10.1021/ja9106226
  34. Naodovic, M.; Yamamoto, H. Chem. Rev. 2008, 108, 3132-3148. https://doi.org/10.1021/cr068413r
  35. Alvarez-Corral, M.; Munoz-Dorado, M.; Rodriguez-Garcia, I. Chem. Rev. 2008, 108, 3174-3198. https://doi.org/10.1021/cr078361l
  36. Thompson, J. L.; Davies, H. M. L. J. Am. Chem. Soc. 2007, 129, 6090-6091. https://doi.org/10.1021/ja069314y
  37. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Zanatta, N.; Bonacorso, H. G. Chem Rev. 2008, 108, 2015-2050. https://doi.org/10.1021/cr078399y
  38. Parvulescu, V. I.; Hardacre, C. Chem Rev. 2007, 107, 2615-2665. https://doi.org/10.1021/cr050948h
  39. Whitehead, J. A.; Lawrance G. A.; McCluskey, A. Green Chem. 2004, 6, 313- 315. https://doi.org/10.1039/b406148a
  40. Wong, F. M.; Wang, J.; Hengge, A. C.; Wu, W. Org. Lett. 2007, 9, 1663-1665. https://doi.org/10.1021/ol070345n
  41. Mueller, P.; Allenbach, Y. F.; Bernardinelli, G. Helv. Chim. Acta. 2003, 86, 3164-3178. https://doi.org/10.1002/hlca.200390257
  42. Yilmaz, M.; Pekel, A. T. Synth. Commun. 2001, 31, 3871-3876. https://doi.org/10.1081/SCC-100108239
  43. Lee, Y. R. Tetrahedron 1995, 51, 3087-3094. https://doi.org/10.1016/0040-4020(95)00070-O
  44. Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. J. Org. Chem. 1985, 50, 3467-3473. https://doi.org/10.1021/jo00219a010

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