Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Hydrated Ferric Sulfate [Fe2(SO4)3·xH2O]: An Efficient and Reusable Catalyst for One-Pot Synthesis of 2H-Indazolo[2,1-b]phthalazine-triones

  • Choudhury, Abhik (Department of Chemistry, Indian Institute of Technology Guwahati) ;
  • Ali, Shahzad (Department of Chemistry, Indian Institute of Technology Guwahati) ;
  • Khan, Abu T. (Department of Chemistry, Indian Institute of Technology Guwahati)
  • Received : 2013.09.02
  • Accepted : 2015.05.20
  • Published : 2015.08.31
Download PDF
⟨ Previous Next ⟩

Abstract

Hydrated ferric sulfate can be used as an efficient and reusable catalyst for the synthesis of 2H-indazolo[2,1-b]phthalazine-trione derivatives via one-pot three-component condensation reaction of phthalhydrazide, aromatic aldehydes and cyclic-1,3-diketones in ethanol under reflux conditions.

Keywords

References

  1. Li, L.; Zhu, L.; Zhang, X.; Zhang, G.; Qu, G. Can. J. Chem. 2005, 83, 1120. https://doi.org/10.1139/v05-136
  2. Zhang, X.; Li, L.; Zhang, G. Green Chem. 2003, 5, 646. https://doi.org/10.1039/B305772K
  3. Zhang, G.; Liu, Q.; Shi, L.; Wang, J. Tetrahedron 2008, 64, 339. https://doi.org/10.1016/j.tet.2007.10.097
  4. Shi, L.; Zhang, G.; Pan, F. Tetrahedron 2008, 64, 2572. https://doi.org/10.1016/j.tet.2008.01.027
  5. Khan, A. T.; Das, D. K.; Khan, M. M. Tetrahedron Lett. 2011, 52, 4539. https://doi.org/10.1016/j.tetlet.2011.06.080
  6. Khan, A. T.; Ghosh, A.; Basha, R. S.; Mir, M. H. Asian. J. Org. Chem. 2012, 2, 126.
  7. (a) Khan, A. T.; Basha, R. S.; Lal, M. Tetrahedron Lett. 2012, 53, 2211. https://doi.org/10.1016/j.tetlet.2012.02.078
  8. (b) Khan, A. T.; Das, D. K. Tetrahedron Lett. 2012, 53, 2345. https://doi.org/10.1016/j.tetlet.2012.02.114
  9. (a) Domling, A. Chem. Rev. 2006, 106, 17. https://doi.org/10.1021/cr0505728
  10. (b) D’Souza, D. M.; Muller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095 https://doi.org/10.1039/B608235C
  11. (c) Harborne, J. B.;Cariou, C. C. A.; Clarkson, G. J.; Shipman, M. J. J. Org. Chem. 2008, 73, 9762. https://doi.org/10.1021/jo801664g
  12. (d) 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
  13. Baxter, H.; Moss, G. P. Phytochemical Dictionary - A Handbook of Bioactive Compounds from Plants, 2nd eds., Taylor & Francis, London: UK, 1999.
  14. Grasso, S.; De Sarro, G.; De Sarro, A.; Micale, N.; Zappala, M.; Puia, G.; Baraldi, M.; De Micheli, C. J. Med. Chem. 2000, 43, 2851. https://doi.org/10.1021/jm001002x
  15. Nomoto, Y.; Obase, H.; Takai, H.; Teranishi, M.; Nakamura, J.; Kubo, K. Chem. Pharm. Bull. 1990, 38, 2179. https://doi.org/10.1248/cpb.38.2179
  16. Watanabe, N.; Kabasawa, Y.; Takase, Y.; Matsukura, M.; Miyazaki, K.; Ishihara, H.; Kodama, K.; Adachi, H. J. Med. Chem. 1998, 41, 3367. https://doi.org/10.1021/jm970815r
  17. El-Sakka, S. S.; Soliman, A. H.; Imam, A. M. Afinidad 2009, 66, 167.
  18. Ryu, C.-K.; Park, R.-E.; Ma, M.-Y.; Nho, J.-H. Bioorg. Med. Chem. Lett. 2007, 17, 2577. https://doi.org/10.1016/j.bmcl.2007.02.003
  19. Li, J.; Zhao, Y. F.; Yuan, X. Y.; Xu, J. X.; Gong, P. Molecules 2006, 11, 574. https://doi.org/10.3390/11070574
  20. Sinkkonen, J.; Ovcharenko, V.; Zelenin, K. N.; Bezhan, I. P.; Chakchir, B. A.; Al-Assar, F.; Pihlaja, K. Eur. J. Org. Chem. 2002, 2046.
  21. Sung, J. S.; Lee, H.-J.; Suh, M.-E.; Choo, H.-Y. P.; Lee, S. K.; Park, H. J.; Kim, C.; Park, S. W.; Lee, C.-O.; Bioorg. Med.Chem. 2004, 12, 3683. https://doi.org/10.1016/j.bmc.2004.04.014
  22. Piatnitski, E. L.; Duncton, M. A. J.; Kiselyov, A. S.; Katoch-Rouse, R.; Sherman, D.; Milligan, D. L.; Balagtas, C.; Wong, W. C.; Kawakami, J.; Doody, J. F. Bioorg. Med. Chem. Lett. 2005, 15, 4696. https://doi.org/10.1016/j.bmcl.2005.07.064
  23. Duncton, M. A. J.; Piatnitski, E. L.; Katoch-Rouse, R.; Smith, L. M.; Kiselyov, A. S.; Milligan, D. L.; Balagtas, C.; Wong, W. C.; Kawakami, J.; Doody, J. F. Bioorg. Med. Chem. Lett. 2006, 16, 1579. https://doi.org/10.1016/j.bmcl.2005.12.045
  24. Wu, H.; Chen, X. M.; Wan, Y.; Xin, H. Q.; Xu, H. H.; Ma, R.; Yue, C. H.; Pang, L. L. Lett. Org. Chem. 2009, 6, 219. https://doi.org/10.2174/157017809787893127
  25. (a) Shaterian, H. R.; Ghashang, M.; Feyzi, M. Appl. Catal. A: Gen. 2008, 345, 128. https://doi.org/10.1016/j.apcata.2008.04.032
  26. (b) Khurana, J. M.; Devanshi, M. Tetrahedron Lett. 2009, 50, 7300. https://doi.org/10.1016/j.tetlet.2009.10.032
  27. (c) Sabitha, G.; Srinivas, C.; Raghavendar, A.; Yadav, J. S. Helv. Chim. Acta 2010, 93, 1375. https://doi.org/10.1002/hlca.200900378
  28. (d) Ghorbani-Vaghei, R.; Karimi-Nami, R.; ToghraeiSemiromi, Z.; Amiri, M.; Ghavidel, M. Tetrahedron 2011, 67, 1930. https://doi.org/10.1016/j.tet.2011.01.024
  29. (e) Mosaddegh, E.; Hassankhani, A. Tetrahedron Lett. 2011, 52, 488. https://doi.org/10.1016/j.tetlet.2010.08.099
  30. (a) Sheradsky, T.; Moshenberg, R. J. Org. Chem. 1986, 51, 3123. https://doi.org/10.1021/jo00366a008
  31. (b) Csampai, A.; Kormendy, K.; Ruff, F. Tetrahedron. 1991 47, 4457. https://doi.org/10.1016/S0040-4020(01)87114-3
  32. (c) Ramtohup, Y. K.; James, M. N. G.; Vederas, J. C. J. Org. Chem. 2002, 67, 3169. https://doi.org/10.1021/jo0157831
  33. (d) Liu, L. P.; Lu, J. M.; Shi, M. Org. Lett. 2007, 9, 1303. https://doi.org/10.1021/ol070178r
  34. (e) Shukla, G.; Verma, R. K.; Verma, G. K.; Singh, M.S. Tetrahedron Lett. 2011, 52, 7195. https://doi.org/10.1016/j.tetlet.2011.10.136
  35. (f) Kidwai, M.; Jahan, A., Chauhan, R., Mishra, N. K. Tetrahedron Lett. 2012, 53, 1728. https://doi.org/10.1016/j.tetlet.2012.01.095
  36. (g) Shekouhy, M.; Hasaninejad, A. Ultrason. Sonochem. 2012, 19, 307. https://doi.org/10.1016/j.ultsonch.2011.07.011
  37. (h) Sayyafi, M.; Seyyedhamze, M.; Khavasi, H. R.; Bazgir, A. Tetrahedron 2008, 64, 2375. https://doi.org/10.1016/j.tet.2008.01.006
  38. (i) Shaterian, H. R.; Hosseinian, A.; Ghashang, M. ARKIVOC 2009, ii, 59.

Cited by

  1. Synthesis of tetrasubstituted 1H-indazolo[1,2-b]phthalazinedione derivatives bearing three-dimensional turbine-type structures via domino reaction of phthalhydrazide and vinylketones vol.7, pp.61, 2017, https://doi.org/10.1039/C7RA06856E
  2. Ultrasound-assisted synthesis of heterocyclic compounds vol.24, pp.3, 2020, https://doi.org/10.1007/s11030-019-09964-1