Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2017, Article ID 5610707, 6 pages
https://doi.org/10.1155/2017/5610707
Research Article

Enaminonitrile as Building Block in Heterocyclic Synthesis: Synthesis of Novel 4H-Furo[2,3-d][1,3]oxazin-4-one and Furo[2,3-d]pyrimidin-4(3H)-one Derivatives

Chemistry Department, Faculty of Science, Ain Shams University, Abbasia, Cairo 11566, Egypt

Correspondence should be addressed to Manal M. El-Shahawi; moc.oohay@13iwahahsle

Received 24 January 2017; Accepted 28 March 2017; Published 20 April 2017

Academic Editor: Xinyong Liu

Copyright © 2017 Manal M. El-Shahawi and Ahmed K. El-Ziaty. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. B. Rumpa, H. K. S. Kumar, and B. Mrityunjay, “Medicinal significance of furan derivatives,” International Journal of Review in Life Sciences, vol. 2, no. 1, pp. 7–16, 2012. View at Google Scholar
  2. C. Paz, M. G. Peter, B. Schmidt et al., “Synthesis and AChE inhibiting activity of 2,4-substituted 6-phenyl pyrimidines,” Journal of the Chilean Chemical Society, vol. 57, no. 3, pp. 1292–1294, 2012. View at Publisher · View at Google Scholar · View at Scopus
  3. V. J. Prasad, R. N. Kumar, A. K. Solomon et al., “One pot synthesis of chromno-pyrano-pyrimidines and evolution of their antimicrobial activity,” Indian Journal of Chemistry, vol. 53B, no. 3, pp. 345–351, 2014. View at Google Scholar
  4. R. Singh and A. Chouhan, “An overview of biological importance of pyrimidines,” World Journal of Pharmacy and Pharmaceutical Sciences, vol. 3, no. 12, pp. 574–597, 2014. View at Google Scholar
  5. J. A. S. Mulla, M. I. A. Khazi, S. I. Panchamukhi, Y.-D. Gong, and I. A. M. Khazi, “Synthesis and pharmacological evaluation of novel thienopyrimidine and triazolothienopyrimidine derivatives,” Medicinal Chemistry Research, vol. 23, no. 6, pp. 3235–3243, 2014. View at Publisher · View at Google Scholar · View at Scopus
  6. I. A. Novakov, M. B. Navrotskii, E. K. Zakharova, and L. L. Brunilina, “C(2)-functionalization of pyrimidin-4(3H)-one derivatives in the synthesis of its biologically active derivatives,” Russian Chemical Bulletin, vol. 64, no. 11, pp. 2545–2561, 2015. View at Publisher · View at Google Scholar
  7. M. Sahu and N. Siddiqui, “A review on biological importance of pyrimidines in the new era,” International Journal of Pharmacy and Pharmaceutical Sciences, vol. 8, no. 5, pp. 8–21, 2016. View at Google Scholar · View at Scopus
  8. M. A. Aziz, R. A. T. Serya, D. S. Lasheen et al., “Discovery of potent VEGFR-2 inhibitors based on furopyrimidine and thienopyrimidne scaffolds as cancer targeting agents,” Scientific Reports, vol. 6, Article ID 24460, 2016. View at Publisher · View at Google Scholar · View at Scopus
  9. M. A. Aziz, R. A. Serya, D. S. Lasheen, and K. A. Abouzid, “Furo[2,3-d]pyrimidine based derivatives as kinase inhibitors and anticancer agents,” Future Journal of Pharmaceutical Sciences, vol. 2, no. 1, pp. 1–8, 2016. View at Publisher · View at Google Scholar
  10. Z. Janeba, A. Holý, R. Pohl et al., “Synthesis and biological evaluation of acyclic nucleotide analogues with a furo[2,3-d]pyrimidin-2(3H)-one base,” Canadian Journal of Chemistry, vol. 88, no. 7, pp. 628–638, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. M. J. Robins, I. Nowak, V. K. Rajwanshi et al., “Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d] pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core,” Journal of Medicinal Chemistry, vol. 50, no. 16, pp. 3897–3905, 2007. View at Publisher · View at Google Scholar · View at Scopus
  12. M. I. Hossain and M. M. H. Bhuiyan, “Synthesis and antimicrobial activities of some new thieno and furopyrimidine derivatives,” Journal of Scientific Research, vol. 1, no. 2, pp. 317–325, 2009. View at Publisher · View at Google Scholar
  13. J. I. Pyo, S. H. Lee, and C. S. Cheong, “A facile synthesis of some substituted furopyrimidine derivatives,” Journal of Heterocyclic Chemistry, vol. 43, no. 4, pp. 1129–1133, 2006. View at Publisher · View at Google Scholar · View at Scopus
  14. R. M. Shaker, “Synthesis of new furo[2,3-d]pyrimidines and furo[3,2-e] [1,2,4]triazolo[1,5-c]pyrimidines,” ARKIVOC, vol. 14, pp. 68–77, 2006. View at Google Scholar
  15. Y. K. Se, J. K. Dong, S. Y. Beom, and H. Y. Kyung, “Synthesis and biological evaluation of furo[2,3-d]pyrimidines as Akt1 kinase inhibitors,” Bulletin of the Korean Chemical Society, vol. 28, no. 7, pp. 1114–1118, 2007. View at Publisher · View at Google Scholar · View at Scopus
  16. Y. Miyazaki, Y. Maeda, H. Sato, M. Nakano, and G. W. Mellor, “Rational design of 4-amino-5,6-diaryl-furo[2,3-d]pyrimidines as potent glycogen synthase kinase-3 inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 6, pp. 1967–1971, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. A. Gangjee, W. Li, L. Lin et al., “Design, synthesis, and X-ray crystal structures of 2,4-diaminofuro[2,3-d]pyrimidines as multireceptor tyrosine kinase and dihydrofolate reductase inhibitors,” Bioorganic and Medicinal Chemistry, vol. 17, no. 20, pp. 7324–7336, 2009. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Bayat, N. Z. Shiraz, and S. H. Hosseini, “A novel approach for the synthesis of furopyrimidine and oxobenzofuran derivatives,” Helvetica Chimica Acta, vol. 93, no. 11, pp. 2189–2193, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. A. Zhao, X. Gao, Y. Wang et al., “Discovery of novel c-Met kinase inhibitors bearing a thieno [2,3-d] pyrimidine or furo [2,3-d] pyrimidine scaffold,” Bioorganic & Medicinal Chemistry, vol. 19, no. 13, pp. 3906–3918, 2011. View at Publisher · View at Google Scholar · View at Scopus
  20. X. Zhang, S. Raghavan, M. Ihnat et al., “The design and discovery of water soluble 4-substituted-2,6-dimethylfuro[2, 3-d]pyrimidines as multitargeted receptor tyrosine kinase inhibitors and microtubule targeting antitumor agents,” Bioorganic and Medicinal Chemistry, vol. 22, no. 14, pp. 3753–3772, 2014. View at Publisher · View at Google Scholar · View at Scopus
  21. M. M. Elshahawi, A. K. EL-Ziaty, J. M. Morsy, and A. F. Aly, “Synthesis and insecticidal efficacy of novel bis quinazolinone derivatives,” Journal of Heterocyclic Chemistry, vol. 53, no. 5, pp. 1443–1448, 2016. View at Publisher · View at Google Scholar
  22. M. A. El-Hashash, M. M. Elshahawi, E. A. Ragab, and S. Nagdy, “Synthesis and antifungal activity of novel quinazolin-4(3H)-one derivatives,” Synthetic Communications, vol. 45, no. 19, pp. 2240–2250, 2015. View at Publisher · View at Google Scholar · View at Scopus
  23. A. K. Elziaty, G. Bassioni, A. M. Hassan, H. A. Derbala, and M. S. Abdel-Aziz, “A synthetic approach to pyrazolopyranopyrimidinones and pyrazolopyranooxazinones as antimicrobial agents,” Journal of Chemistry, vol. 2016, Article ID 5286462, 7 pages, 2016. View at Publisher · View at Google Scholar
  24. A. K. El-Ziaty and S. A. Shiba, “Antibacterial activities of new (E) 2-cyano-3-(3′,4′- dimethoxyphenyl)-2-propenoylamide derivatives,” Synthetic Communications, vol. 37, no. 22, pp. 4043–4057, 2007. View at Publisher · View at Google Scholar · View at Scopus
  25. W. S. I. Abou-Elmagd, A. K. El-Ziaty, and A. A. Abdalha, “Ring transformation and antimicrobial activity of indolyl-substituted 2(3H)-furanones,” Heterocyclic Communications, vol. 21, no. 3, pp. 179–185, 2015. View at Publisher · View at Google Scholar · View at Scopus
  26. A. El-Ziaty, A. Abdalh, A. Hamed, S. Shiba, and A. Abdullha, “Synthesis of novel 2-propenoyl amides, esters, heterocyclic compounds and their screening as antifungal and antibacterial agents,” European Journal of Chemistry, vol. 3, no. 1, pp. 65–70, 2012. View at Publisher · View at Google Scholar
  27. A. K. Elziaty, O. E. A. Mostafa, E. A. El-Bordany, M. Nabil, and H. M. F. Madkour, “Access to new pyranopyrazoles and related heterocycles,” International Journal of Scientific & Engineering Research, vol. 5, no. 1, pp. 727–735, 2014. View at Google Scholar
  28. X. Feng, J.-C. Lancelot, H. Prunier, and S. Rault, “First synthesis of 4H-Furo[3,2-f]pyrrolo[1,2-a][1,4]diazepines,” Journal of Heterocyclic Chemistry, vol. 33, no. 6, pp. 2007–2011, 1996. View at Publisher · View at Google Scholar · View at Scopus