Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Very Efficient and Rapid Catalyst-free One-pot Three Component Synthesis of 2,5-Dihydro-5-imino-2-methylfuran-3,4-dicarboxylate Derivatives Under Ultrasound Irradiation

  • Received : 2012.08.14
  • Accepted : 2012.09.27
  • Published : 2012.12.20
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Abstract

We report a fast, efficient, and facile route for the synthesis of 2,5-dihydro-5-imino-2-methylfuran-3,4-dicarboxylate derivatives from the isocyanide, dialkyl acetylenedicarboxylate and acetic anhydride under ultrasound-assisted conditions. Utilization of easy reaction conditions, very high to excellent yields, and short reaction times makes this manipulation potentially very useful.

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References

  1. Zhu, J.; Bienayme, H. Multicomponent Reactions; Wiley-Weinheim: 2005.
  2. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123. https://doi.org/10.1021/ar9502083
  3. Domling, A. Chem. Rev. 2006, 106, 17. https://doi.org/10.1021/cr0505728
  4. Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. https://doi.org/10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
  5. Akritopoulou-Zanze, I. Curr. Opin. Chem. Biol. 2008, 12, 1. https://doi.org/10.1016/j.cbpa.2008.02.016
  6. Shevchenko, N. E. Chem. Heterocycl. Compd. 1999, 35, 164. https://doi.org/10.1007/BF02251702
  7. Bastian, G.; Royer, R.; Cavier, R. Eur. J. Med. Chem. 1983, 21, 365.
  8. Kupchan, S. M.; Eakin, M. A.; Thomas, A. M. J. Med. Chem. 1971, 111, 1147.
  9. Bandurraga, M. M.; Fenical, W.; Donovan, S. F.; Clardy, J. J. Am. Chem. Soc. 1982, 104, 6463. https://doi.org/10.1021/ja00387a059
  10. Kobayashi, J.; Ohizumi, Y.; Nakamura, H. Tetrahedron Lett. 1986, 27, 2113. https://doi.org/10.1016/S0040-4039(00)84462-7
  11. Hofnung, M.; Quillardet, V. M.; Touati, E. Res. Microbiol. 2002, 153, 427. https://doi.org/10.1016/S0923-2508(02)01354-2
  12. Khan, M. W.; Alam, M. J.; Rashid, M. A.; Chowdhury, R. Bioorg. Med. Chem. 2005, 13, 4796. https://doi.org/10.1016/j.bmc.2005.05.009
  13. Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Pergamon: 1996.
  14. Pei, W. P.; Pei, J.; Li, S. H.; Ye, X. L. Synthesis 2000, 2069.
  15. Mason, T. J.; Peters, D. Practical Sonochemistry; EllisHorwood: 2002.
  16. Luche, J. L. Synthetic Organic Sonochemistry; Plenum Press: 1998.
  17. Li, J. T.; Bian, Y. J.; Zang, H. J.; Li, T. S. Synth. Commun. 2002, 32, 547. https://doi.org/10.1081/SCC-120002400
  18. Zang, H. J.; Wang, M. L.; Cheng, B. W.; Song, J. Ultrason. Sonochem. 2009, 16, 301. https://doi.org/10.1016/j.ultsonch.2008.09.003
  19. Ramazani, A.; Zeinali Nasrabadi, F.; Karimi, Z.; Rouhani, M. Bull. Korean Chem. Soc. 2011, 32, 2700. https://doi.org/10.5012/bkcs.2011.32.8.2700
  20. Ramazani, A.; Rezaei, A.; Mahyari, A.; Rouhani, M.; Khoobi, M. Helv. Chim. Acta 2010, 93, 2033. https://doi.org/10.1002/hlca.201000057
  21. Ramazani, A.; Tofangchi Mahyari, A.; Rouhani, M.; Rezaei, A. Tetrahedron Lett. 2009, 50, 5625. https://doi.org/10.1016/j.tetlet.2009.07.115
  22. Ramazani, A.; Dastanra, K.; Zeinali Nasrabadi, F.; Karimi, Z.; Rouhani, M.; Hosseini, M. Turk. J. Chem. 2012, 36, 476.
  23. Ramazani, A.; Zeinali Nasrabadi, F.; Abdian, B.; Rouhani, M. Bull. Korean Chem. Soc, 2012, 33, 453. https://doi.org/10.5012/bkcs.2012.33.2.453
  24. Ramazani, A.; Rouhani, M.; Rezaei, A.; Shajari, N.; Souldozi, A. Helv. Chim. Acta 2011, 94, 282. https://doi.org/10.1002/hlca.201000219
  25. Mason, T. J.; Lorimer, J. P.; Mistry, B. P. Tetrahedron 1985, 41, 5201. https://doi.org/10.1016/S0040-4020(01)96767-5
  26. Shaabani, A.; Rezayan, A. H.; Ghasemi, S.; Sarvary, A. Tetrahedron Lett. 2009, 50, 1456. https://doi.org/10.1016/j.tetlet.2009.01.069

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