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Efficient One-Pot Synthesis of Acridinediones by Indium(III) Triflate-Catalyzed Reactions of β-Enaminones, Aldehydes, and Cyclic 1,3-Dicarbonyls

  • To, Quang Huy (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)
  • Received : 2011.12.15
  • Accepted : 2011.12.30
  • Published : 2012.04.20

Abstract

An efficient one-pot synthesis of acridinediones by $In(OTf)_3$-catalyzed reactions was developed starting from ${\beta}$-enaminones, aldehydes, and cyclic 1,3-diketones. The key strategies of these reactions involve domino Knoevenagel condensation/Michael addition/cyclodehydration reaction.

Keywords

References

  1. Shchekotikhin, Y. M.; Nikolaeva, T. G.; Shub, G. M.; Kriven'ko, A. P. Pharmaceut. Chem. J. 2001, 35, 206. https://doi.org/10.1023/A:1010484013306
  2. Pyrko, A. N. Russ. J. Org. Chem. 2008, 44, 1215. https://doi.org/10.1134/S1070428008080198
  3. Kidwai, M.; Bhatnagar, D. Tetrahedron Lett. 2010, 51, 2700. https://doi.org/10.1016/j.tetlet.2010.03.033
  4. Tu, S.; Zhang, X.; Shi, F.; Li, T.; Wang, Q.; Zhu, X.; Zhang, J.; Xu, J. J. Heterocycl. Chem. 2005, 42, 1155. https://doi.org/10.1002/jhet.5570420618
  5. Gamage, S. A.; Spicer, J. A.; Atwell, G. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1999, 42, 2383. https://doi.org/10.1021/jm980687m
  6. Palani, K.; Thirumalai, D.; Ambalavanan, P.; Ponnuswamy, M. N.; Ramakrishnan, V. T. J. Chem. Crystallogr. 2005, 35, 751. https://doi.org/10.1007/s10870-005-3880-2
  7. Wainwright, M. J. Antimicrob. Chemother. 2001, 47, 1.
  8. Srivastava, A.; Nizamuddin, C. Indian J. Heterocycl. Chem. 2004, 13, 261.
  9. Venkatesan, K.; Pujari, S. S.; Srinivasan, K. V. Synth. Commun. 2009, 39, 228.
  10. Balalaie, S.; Chadegani, F.; Darviche, F.; Bijanzadeh, H. R. Chin. J. Chem. 2009, 27, 1953. https://doi.org/10.1002/cjoc.200990328
  11. Li, L.-B.; Ji, S.-J.; Liu, Y. Chin. J. Chem. 2008, 26, 979. https://doi.org/10.1002/cjoc.200890208
  12. Das, B.; Thirupathi, P.; Mahender, I.; Reddy, V. S.; Rao, Y. K. J. Mol. Catal. A: Chem. 2006, 247, 233. https://doi.org/10.1016/j.molcata.2005.11.048
  13. Kaya, M.; Yildirir, Y.; Celik, G. Y. Med. Chem. Res. 2011, 20, 293. https://doi.org/10.1007/s00044-010-9321-6
  14. Jin, T.-S.; Zhang, J.-S.; Guo, T.-T.; Wang, A.-Q.; Li, T.-S. Synthesis 2004, 2001.
  15. Wang, X.-S.; Zhang, M.-M.; Zeng, Z.-S.; Shi, D.-Q.; Tu, S.-J.; Wei, X.-Y.; Zong, Z.-M. ARKIVOC 2006, (ii), 117.
  16. Shi, D.-Q.; Ni, S.-N.; Yang, F.; Shi, J.-W.; Dou, G.-L.; Li, X.- Y.; Wang, X.-S. J. Heterocycl. Chem. 2008, 45, 653. https://doi.org/10.1002/jhet.5570450303
  17. Li, Y.-L.; Zhang, M.-M.; Wang, X.-S.; Shi, D.-Q.; Tu, S.-J.; Wei, X.-Y.; Zong, Z.-M. J. Chem. Res. 2005, 9, 600.
  18. Singh, S. K.; Singh, K. N. J. Heterocycl. Chem. 2011, 48, 69. https://doi.org/10.1002/jhet.508
  19. Hua, G.-P.; Li, T.-J.; Zou, X.; Tu, S.-J.; Zhu, S.-L.; Zhang, X.- J.; Ji, S.-J.; Zhang, Y. Chin. J. Org. Chem. 2005, 25, 1294.
  20. Wang, X.-S.; Zhang, M.-M.; Jiang, H.; Shi, D.-Q.; Tu, S.-J.; Wei, X.-Y.; Zong, Z.-M. Synthesis 2006, 4187.
  21. Kazahaya, K.; Hamada, N.; Ito, S.; Sato, T. Synlett 2002, 1535.
  22. Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron 2002, 58, 7897. https://doi.org/10.1016/S0040-4020(02)00897-9
  23. Mineno, T. Tetrahedron Lett. 2002, 43, 7975. https://doi.org/10.1016/S0040-4039(02)01864-6
  24. Nagarajan, R.; Perumal, P. T. Tetrahedron 2002, 58, 1229. https://doi.org/10.1016/S0040-4020(01)01227-3
  25. Chapmann, C. J.; Frost, C. G.; Hartley, J. P.; Whittle, A. J. Tetrahedron Lett. 2001, 42, 773. https://doi.org/10.1016/S0040-4039(00)02122-5
  26. Ali, T.; Chauhan, K. K.; Frost, C. G. Tetrahedron Lett. 1999, 40, 5621. https://doi.org/10.1016/S0040-4039(99)01045-X
  27. Loh, T.-P.; Hu, Q.-Y.; Ma, L.-T. J. Am. Chem. Soc. 2001, 123, 2450. https://doi.org/10.1021/ja005831j
  28. Roussel, P. G.; Turner, N. J.; Dinan, L. N. J. Chem. Soc., Chem. Commun. 1995, 933.
  29. Loh, T.-P.; Hu, Q.-Y.; Tan, K.-T.; Cheng, H.-S. Org. Lett. 2001, 3, 2669. https://doi.org/10.1021/ol016228o
  30. Ghosh, R.; Maiti, S. J. Mol. Catal. A: Chem. 2007, 264, 1. https://doi.org/10.1016/j.molcata.2006.08.086
  31. Jung, D. H.; Lee, Y. R.; Kim, S. H.; Lyoo, W. S. Bull. Korean Chem. Soc. 2009, 30, 1989. https://doi.org/10.5012/bkcs.2009.30.9.1989
  32. Wang, G.-W.; Miao, C.-B. Green Chem. 2006, 8, 1080. https://doi.org/10.1039/b604064k
  33. Shchekotikhin, Y. M.; Getmanenko, Y. A.; Nikolaeva, T. G.; Kriven'ko, A. P. Chem. Heterocycl. Comp. 2001, 37, 1228. https://doi.org/10.1023/A:1013845426393

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