DOI QR코드

DOI QR Code

ZrOCl2·8H2O as an Efficient Catalyst for the Pseudo Four-Component Synthesis of Benzopyranopyrimidines

  • Tavakoli, Hamid Reza ;
  • Moosavi, Sayed Mojtaba ;
  • Bazgir, Ayoob
  • Received : 2012.12.31
  • Accepted : 2013.03.13
  • Published : 2013.04.20

Abstract

An efficient and environmentally benign protocol for the pseudo four-component synthesis of benzopyranopyrimidines via condensation of salicylic aldehydes, malononitrile and various amines catalyzed by $ZrOCl_2{\cdot}8H_2O$ as an inexpensive and eco-friendly catalyst with high catalytic activity under solvent-free conditions is reported. This protocol provides a new and improved method for obtaining benzopyranopyrimidines in terms of good yields, simple experimental procedure and short reaction time.

Keywords

Solvent-free;Malononitrile;Benzopyranopyrimidine;Salicylaldehyde

References

  1. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Buriol, L.; Machado, P. Chem. Rev. 2009, 109, 4140. https://doi.org/10.1021/cr9001098
  2. Tanaka, K.; Toda, F. In Solvent-free Organic Synthesis; Wiley-VCH GmbH: 2003.
  3. Bagley, M. C.; Lubinu, M. C. Top. Heterocycl. Chem. 2006, 31.
  4. Multicomponent Reactions; Zhu, J., Bienayme, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
  5. Ramon, D. J.; Yus, M. Angew. Chem. 2005, 117, 1628. https://doi.org/10.1002/ange.200460548
  6. Nandi, G. C.; Samai, S.; Kumar, R.; Singh, M. S. Tetrahedron Lett. 2009, 50, 7220. https://doi.org/10.1016/j.tetlet.2009.10.055
  7. Baraldi, P. G.; Tabrizi, M. A.; Gessi, S.; Borea, P. A. Chem. Rev. 2008, 108, 238. https://doi.org/10.1021/cr0682195
  8. Sharma, R.; Goyal, R. D.; Praskash, L. Indian J. Chem. Sect. B 1992, 31. 719.
  9. Noda, K.; Nakagawa, A.; Yamagata, K.; Mujata, S.; Ide, H. JPN Patent 75−157. Chem. Abstr. 1976, 85, 5675p.
  10. Ahluwalia, V. K.; Batla, R.; Khurana, R.; Kumar, R. Indian J. Chem. Sect. B 1990, 29. 1141.
  11. Hadfield, J. A.; Pavlidis, V. H.; Perry, P. J.; McGown, A. T. Anti-Cancer Drugs 1999, 10, 591. https://doi.org/10.1097/00001813-199907000-00011
  12. Firouzabadi, H.; Jafarpour, M. J. Iran. Chem. Soc. 2008, 5, 159. https://doi.org/10.1007/BF03246110
  13. Ghosh, R.; Maiti, S. Chakraborty, A. Tetrahedron Lett. 2005, 46. 147. https://doi.org/10.1016/j.tetlet.2004.10.164
  14. Mirkhani, V.; Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Abdollahi-Alibeik, M.; Kargar, H. Appl. Catal. A: Gen. 2007, 325, 99. https://doi.org/10.1016/j.apcata.2007.03.016
  15. Dabiri, M.; Arvin-Nezhad, H.; Khavasi, H. R.; Bazgir, A. Tetrahedron 2007, 63. 1770. https://doi.org/10.1016/j.tet.2006.12.043
  16. Dabiri, M.; Azimi, S. C.; Khavasi, H. R.; Bazgir, A. Tetrahedron 2008, 64. 7307. https://doi.org/10.1016/j.tet.2008.05.063
  17. Jadidi, K.; Ghahremanzadeh, R.; Bazgir, A. Tetrahedron 2009, 65. 2005. https://doi.org/10.1016/j.tet.2009.01.013
  18. Ghahremanzadeh, R.; Amanpour, T.; Bazgir, A. Tetrahedron Lett. 2010, 51. 4202. https://doi.org/10.1016/j.tetlet.2010.06.014
  19. Gupta, A. K.; Kumari, K.; Singh, N.; Raghuvanshi, D. S.; Singh, K. N. Tetrahedron Lett. 2012, 53. 650. https://doi.org/10.1016/j.tetlet.2011.11.116

Cited by

  1. Heteropolyacid@creatin-halloysite clay: an environmentally friendly, reusable and heterogeneous catalyst for the synthesis of benzopyranopyrimidines 2017, https://doi.org/10.1007/s11164-017-3016-2
  2. A novel, facile, rapid, solvent free protocol for the one pot green synthesis of chromeno[2,3-d]pyrimidines using reusable nano ZnAl2O4 – a NOSE approach and photophysical studies vol.5, pp.9, 2015, https://doi.org/10.1039/C4RA16263C
  3. Solvent-free sonochemical multi-component synthesis of benzopyranopyrimidines catalyzed by polystyrene supported p-toluenesulfonic acid vol.71, pp.14, 2015, https://doi.org/10.1016/j.tet.2015.02.019
  4. Synthesis of benzopyrano[2,3-d]pyrimidines using silica-bonded N-propylpiperazine sodium N-propionate as heterogeneous solid base catalyst under solvent-free conditions vol.147, pp.6, 2016, https://doi.org/10.1007/s00706-015-1552-2
  5. A review on green Lewis acids: zirconium(IV) oxydichloride octahydrate (ZrOCl2·8H2O) and zirconium(IV) tetrachloride (ZrCl4) in organic chemistry vol.42, pp.5, 2016, https://doi.org/10.1007/s11164-015-2260-6
  6. Synthesis, Characterization, and Heterogeneous Catalytic Activity of Sulfamic Acid Functionalized Magnetic IRMOF-3 vol.2019, pp.6, 2019, https://doi.org/10.1002/ejic.201801054