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Iodine-Catalyzed One-Pot Synthesis of 2H-Pyrans by Domino Knoevenagel/6π-Electrocylization

  • Jung, Ene-Jin (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Lee, Ha-Jin (Korea Basic Science Institute, Jeonju Center)
  • 발행 : 2009.11.20

초록

키워드

참고문헌

  1. Hsung, R. P.; Kurdyumov, A. V.; Sydorenko, N. Eur. J. Org. Chem. 2005, 23.
  2. Tang, Y.; Oppenheimer, J.; Song, Z.; You, L.; Zhang, X.; Hsung, R. P. Tetrahedron 2006, 62, 10785. https://doi.org/10.1021/ol801406b
  3. McKee, T.; Fuller, R. W.; Covington, C. D.; Cardellina II, J. H.; Gulakowski, R. J.; Krepps, B. L.; McMahon, J. B.; Boyd, M. R. J. Nat. Prod. 1996, 59, 754 https://doi.org/10.1021/np9603784
  4. Kumar, S.; Hernamdez, D.; Hoa, B.; Lee, Y.; Yang, J. S.; McCurdy, A. Org. Lett. 2008, 10, 3761. https://doi.org/10.1021/ol801406b
  5. Rawat, M.; Prutyanov, V.; Wulff, W. D. J. Am. Chem. Soc. 2006, 128, 11044 https://doi.org/10.1021/ja0568852
  6. Abd, E.; Hisham, A. Pharmazie 1997, 52, 28.
  7. Chen, I.-S.; Wu, S.-J.; Tsai, I. J.; Wu, T.-S.; Pezzuto, J. M.; Lu, M. C.; Chai, H.; Suh, N.; Teng, C.-M. J. Nat. Prod. 1994, 57, 1206. https://doi.org/10.1021/ol0523042
  8. Magiatis, P.; Melliou, E.; Skaltsounis, A.-L.; Mitaku, S.; L$\'{e}$once, S.; Renard, P.; Pierr$\'{e}$, A.; Atassi, G. J. Nat. Prod. 1998, 61, 982 https://doi.org/10.1002/adsc.200700375
  9. Krasnaya, Zh. A.; Prokof'ev, E. P.; Kucherov, V. F. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 1979, 816. https://doi.org/10.1021/jo0708745
  10. Krasnaya, Zh. A.; Stytsenko, T. S.; Bogdanov, V. S. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 1988, 1815 https://doi.org/10.1002/adsc.200800624
  11. Lee, Y. R.; Kim, D. H.; Shim, J.-J.; Kim, S. K.; Park, J. H.; Cha, J. S.; Lee, C.-S. Bull. Korean Chem. Soc. 2002, 23, 998 https://doi.org/10.1021/ja01330a038
  12. Lee, Y. R.; Choi, J. H.; Trinh, D. T. L.; Kim, N. W. Synthesis 2005, 3026. https://doi.org/10.1016/S0040-4039(01)02235-3
  13. Lee, Y. R.; Kim, D. H. Synthesis 2006, 603
  14. Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. Org. Lett. 2006, 8, 2491 https://doi.org/10.1016/j.tetlet.2006.03.182
  15. Kurdyumov, A. V.; Lin, N.; Hsung, R. P.; Gullickson, G. C.; Cole, K. P.; Sydorenko, N.; Swidorski, J. J. Org. Lett. 2006, 8, 191 https://doi.org/10.1021/ol0523042
  16. Hubert, C.; Moreau, J.; Batany, J.; Duboc, A.; Hurvois, J.-P.; Renaud, J.-L. Adv. Synth. Catal. 2008, 350, 40 https://doi.org/10.1021/jo0486239
  17. Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. J. Org. Chem. 2007, 72, 6534. https://doi.org/10.1021/jo0612473
  18. Ren, Y. M.; Cai, C. Org. Prep. Proced. Int. 2008, 40, 101. https://doi.org/10.1016/S0040-4039(02)02373-0
  19. Mao, J.; Hua, Q.; Xie, G.; Guo, J.; Yao, Z.; Shi, D.; Ji, S. Adv. Synth. Catal. 2009, 351, 635 https://doi.org/10.1139/v66-350
  20. Whitmore, F. C.; Rothrock, H. S. J. Am. Chem. Soc. 1933, 55, 1106 https://doi.org/10.1021/ol035663a
  21. Ramalinga, K.; Vijayalalshimi, P.; Kaimal, T. N. B. Tetrahedron Lett. 2002, 43, 879 https://doi.org/10.1016/S0040-4039(03)00032-7
  22. Chavan, S. P.; Kale, R. R.; Shivasankar, K.; Chandake, S. I.; Benjamin, S. B. Synthesis 2003, 2695 https://doi.org/10.1016/j.tetlet.2004.08.044
  23. Bosco, J. W. J.; Agrahari, A.; Saikia, A. K. Tetrahedron Lett. 2006, 47, 4065 https://doi.org/10.1080/00397910802654724
  24. Karimi, B.; Golshani, B. Synthesis 2002, 784. https://doi.org/10.1039/b514635f
  25. Basu, M. K., Samajda, S.; Becker, F. F.; Banik, B. K. Synlett 2002, 319 https://doi.org/10.1002/anie.200701392
  26. Sun, J. W.; Dong, Y. M.; Cao, L. Y. J. Org. Chem. 2004, 69, 8932 https://doi.org/10.1021/jo0486239
  27. Varala, R.; Nuvula, S.; Adapa, S. R. J. Org. Chem. 2006, 71, 8283 https://doi.org/10.1016/j.molcata.2006.11.054
  28. Yadav, J. S.; Reddy, B. V. S.; Sadasiv, K.; Satheesh, G. Tetrahedron Lett. 2002, 43, 9695. https://doi.org/10.1021/np50032a035
  29. Wang, S. Y.; Ji, S. J.; Loh, T. P. Synlett 2003, 2377 https://doi.org/10.1021/np50041a009
  30. Rutherford, K. G.; Mamer, O. A.; Prokipcak, J. M.; Jobin, R. A. Can. J. Chem. 1966, 44, 2337 https://doi.org/10.1016/S0031-9422(00)85006-2
  31. Hessian, K. O.; Flynn, B. L. Org. Lett. 2003, 5, 4377 https://doi.org/10.1021/ol035663a
  32. Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959 https://doi.org/10.1021/jo00150a028
  33. Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 7187 https://doi.org/10.1021/np50021a023
  34. Sashidhara, K. V.; Rosaiah, J. N.; Kumar, A. Synth. Commun. 2009, 39, 2288 https://doi.org/10.1016/j.phytochem.2009.05.004
  35. Wu, J.; Xia, H.-G.; Gao, K. Org. Biomol. Chem. 2006, 4, 126 https://doi.org/10.1055/s-2008-1081298
  36. Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Yamamoto, Y. Angew. Chem. Int. Ed. 2007, 46, 4764 https://doi.org/10.1021/jf051478v
  37. Cravotto, G.; Nano, G. M.; Tagliapietra, S. Synthesis 2001, 49 https://doi.org/10.1055/s-2004-827153
  38. Kidwai, M.; Bansal, V.; Mothsra, P.; Saxena, S.; Somvanshi, R. K.; Dey, S.; Singh, T. P. J. Mol. Catal. A. Chem. 2007, 268, 76 https://doi.org/10.1016/0305-1978(96)00077-4
  39. Ahmad, S. J. Nat. Prod. 1984, 47, 391 https://doi.org/10.1055/s-2004-827153
  40. Mitaku, S.; Skaltsounis, A.-L.; Tillequin, F.; Koch, M.; Pusset, J.; Chauviere, G. J. Nat. Prod. 1985, 48, 772 https://doi.org/10.1021/np50041a009
  41. Ulubelen, A. Phytochemistry 1984, 23, 2123 https://doi.org/10.1016/S0031-9422(00)85006-2
  42. Bowen, I. H.; Lewis, J. R. Lloydia 1978, 41, 184
  43. Tantivatana, P.; Ruangrungsi, N.; Vaisiroiroj, V.; Lankin, D. C.; Bhacca, N. S.; Borris, R. P.; Cordell, G. A.; Johnson, L. F. J. Org. Chem. 1983, 48, 268 https://doi.org/10.1021/jo00150a028
  44. Munoz, M. A.; Torres, R.; Cassels, B. K. J. Nat. Prod. 1982, 45, 367 https://doi.org/10.1021/np50021a023
  45. Staerk, D.; Kesting, J. R.; Sairafianpour, M.; Witt, M.; Asili, J.; Emami, S. A.; Jaroszewski, J. W. Phytochemistry 2009, 70, 1055 https://doi.org/10.1016/j.phytochem.2009.05.004
  46. Ea, S.; Giacometti, S.; Ciccolini, J.; Akhmedjanova, V.; Aubert, C. Planta Med. 2008, 74, 1265 https://doi.org/10.1055/s-2008-1081298
  47. Cantrell, C. L.; Schrader, K. K.; Mamonov, L. K.; Sitpaeva, G. T.; Kustova, T. S.; Dunbar, C.; Wedge, D. E. J. Agr. Food Chem. 2005, 53, 7741 https://doi.org/10.1021/jf051478v
  48. Hanawa, F.; Fokialakis, N.; Skaltsounis, A.-L. Planta Medica 2004, 70, 531 https://doi.org/10.1055/s-2004-827153
  49. Campbell, W. E.; Bean, A. Biochem. Syst. Ecol. 1996, 24, 591 https://doi.org/10.1016/0305-1978(96)00077-4
  50. Hanawa, F.; Fokialakis, N.; Skaltsounis, A.-L. Planta Medica 2004, 70, 531 https://doi.org/10.1055/s-2004-827153

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  11. Recent Advances in the Synthesis of 2H-Pyrans vol.24, pp.16, 2019, https://doi.org/10.3390/molecules24162904
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