Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Facile Synthesis of 4-Substituted 3-Exo-methylenechroman Derivatives via Radical Cyclization Starting from Salicylaldehydes

  • Gowrisankar, Saravanan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Ka-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2007.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Synthesis of 4-substituted 3-exo-methylenechroman derivatives was carried out by the n-Bu3SnH-mediated vinyl radical cyclization as the key step starting from various salicylaldehydes.

Keywords

References

  1. Martins, A.; Marquardt, U.; Kasravi, N.; Alberico, D.; Lautens, M. J. Org. Chem. 2006, 71, 4937 https://doi.org/10.1021/jo060552l
  2. Grutter, C.; Alonso, E.; Chougnet, A.; Woggon, W.-D. Angew. Chem. Int. Ed. 2006, 45, 1126 https://doi.org/10.1002/anie.200503123
  3. Bernard, A. M.; Floris, C.; Frongia, A.; Piras, P. P.; Secci, F. Tetrahedron 2004, 60, 449 https://doi.org/10.1016/j.tet.2003.11.018
  4. Koyama, H.; Boueres, J. K.; Miller, D. J.; Berger, J. P.; MacNaul, K. L.; Wang, P.-r.; Ippolito, M. C.; Wright, S. D.; Agrawal, A. K.; Moller, D. E.; Sahoo, S. P. Bioorg. Med. Chem. 2005, 15, 3347 https://doi.org/10.1016/j.bmcl.2005.05.028
  5. Yasunaga, T.; Kimura, T.; Naito, R.; Kontani, T.; Wanibuchi, F.; Tamashita, H.; Nomura, T.; Tsukamoto, S.-i.; Yamaguchi, T.; Mase, T. J. Med. Chem. 1998, 41, 2765 https://doi.org/10.1021/jm9707840
  6. Fang, Y.; Li, C. J. Org. Chem. 2006, 71, 6427 https://doi.org/10.1021/jo060747t
  7. Ye, L.- W.; Sun, X.-L.; Zhu, C.-Y.; Tang, Y. Org. Lett. 2006, 8, 3853 https://doi.org/10.1021/ol0615174
  8. Kaye, P. T.; Musa, M. A.; Nocanda, X. W.; Robinson, R. S. Org. Biomol. Chem. 2003, 1, 1133 https://doi.org/10.1039/b300360d
  9. Amari, G.; Armani, E.; Ghirardi, S.; Delcanale, M.; Civelli, M.; Caruso, P. L.; Galbiati, E.; Lipreri, M.; Rivara, S.; Lodola, A.; Mor, M. Bioorg. Med. Chem. 2004, 12, 3763 https://doi.org/10.1016/j.bmc.2004.05.015
  10. Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055 https://doi.org/10.1021/ol034177k
  11. Parker, K. A.; Mindt, T. L. Org. Lett. 2001, 3, 3875 https://doi.org/10.1021/ol0167199
  12. Jana, S.; Roy, S. C. Tetrahedron Lett. 2006, 47, 5949 https://doi.org/10.1016/j.tetlet.2006.06.064
  13. Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Chem. Soc., Chem. Commun. 1991, 1248
  14. Booth, S. E.; Jenkins, P. R.; Swain, C. J. J. Braz. Chem. Soc. 1998, 9, 389
  15. Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J. B. J. Chem. Soc., Perkin Trans. 1 1994, 3499
  16. Grigg, R.; Kongkathip, N.; Kongkathip, B.; Luangkamin, S.; Donads, H. A. Tetrahedron 2001, 57, 7965 https://doi.org/10.1016/S0040-4020(01)00771-2
  17. Gowrisankar, S.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2006, 47, 5785 https://doi.org/10.1016/j.tetlet.2006.05.186
  18. Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Tetrahedron 2006, 62, 4052 https://doi.org/10.1016/j.tet.2006.02.038
  19. Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2005, 46, 4859 https://doi.org/10.1016/j.tetlet.2005.05.057
  20. Park, D. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1440 https://doi.org/10.5012/bkcs.2005.26.9.1440
  21. Gowrisankar, S.; Lee, H. S.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 2097 https://doi.org/10.5012/bkcs.2006.27.12.2097
  22. Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 929 https://doi.org/10.5012/bkcs.2006.27.6.929
  23. Hiramatsu, N.; Takahashi, N.; Noyori, R.; Mori, Y. Tetrahedron 2005, 61, 8589 https://doi.org/10.1016/j.tet.2005.07.007
  24. Shanmugam, P.; Rajasingh, P. Tetrahedron 2004, 60, 9283 https://doi.org/10.1016/j.tet.2004.07.067
  25. Shanmugam, P.; Rajasingh, P. Tetrahedron Lett. 2005, 46, 3369 https://doi.org/10.1016/j.tetlet.2005.03.086
  26. Shanmugam, P.; Rajasingh, P. Synlett 2005, 939
  27. Ryu, I.; Ogura, S.-i.; Minakata, S.; Komatsu, M. Tetrahedron Lett. 1999, 40, 1515
  28. Lee, E.; Tae, J. S.; Chong, T. H.; Park, Y. C. Tetrahedron Lett. 1994, 35, 129 https://doi.org/10.1016/0040-4039(94)88181-2
  29. Lin, H.; Schall, A.; Reiser, O. Synlett 2005, 2603
  30. Padwa, A.; Rashatasakhon, P.; Ozdemir, A. D.; Willis, J. J. Org. Chem. 2005, 70, 519 https://doi.org/10.1021/jo048314i
  31. Sha, C.-K.; Zhan, C.-K.; Wang, F.-S. Org. Lett. 2000, 2, 2011
  32. DiBiase, S. A.; Lipisko, B. A.; Haag, A.; Wolak, R. A.; Gokel, G. W. J. Org. Chem. 1979, 44, 4640 https://doi.org/10.1021/jo00393a037
  33. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Visali, B.; Narsaiah, A. V.; Nagaiah, K. Eur. J. Org. Chem. 2004, 546

Cited by

  1. High-yielding sequential one-pot synthesis of chiral and achiral α-substituted acrylates via a metal-free reductive coupling reaction vol.12, pp.29, 2014, https://doi.org/10.1039/C4OB00667D
  2. Facile Synthesis of 4-Substituted 3-exo-Methylenechroman Derivatives via Radical Cyclization Starting from Salicylaldehydes. vol.38, pp.34, 2007, https://doi.org/10.1002/chin.200734131
  3. Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives vol.8, pp.None, 2007, https://doi.org/10.3762/bjoc.8.244
  4. Part II: nitroalkenes in the synthesis of heterocyclic compounds vol.4, pp.93, 2007, https://doi.org/10.1039/c4ra08830a
  5. Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules vol.6, pp.44, 2007, https://doi.org/10.1039/c5ra27069c