Article Sidebar

Download
PDF

Main Article Content

Abstract

The present work deals with generation and synthesis of 2-(2- camphoryl)-4-(4-aryl)-4-oxobutanoic acids via Michael reaction condition depending on the type of nucleophilic reagents and medium (acidic or basic). The adducts are used as a key starting materials to synthesize some hetrocycles include pyridazinone, furanone, 1,2- oxazin-5-one, 1.2-diazapine, pyrane and hydroxyl pyridine derivatives. Steric factor plays an important role in regioselectivity. The structure of newly synthesized compounds were elucidated by elemental analysis and spectroscopic data.

Keywords

4-Aryl-4-oxo-but-2-enoic acid Camphor Pyridazin-3-one Furanone 1,2-Oxazinone

Article Details

How to Cite
A. El-Hashash, M., & A. Rizk, S. (2017). Regioselective Diastereotopic Michael Reaction as Building Blocks in Heterocyclic Synthesis. Asian Journal of Organic & Medicinal Chemistry, 2(1), 18–22. https://doi.org/10.14233/ajomc.2017.AJOMC-P57
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. Z. Juranic, L.J. Sterovic, B. Darkulic, T. Stanojkovic, I. Radulovic and S. Juranic, J. Serb. Chem. Soc., 64, 505 (1999).
  2. L.M. Taylor, J.A. Aquilina, J.F. Jamie and R.J.W. Truscott, Exp. Eye Res., 75, 165 (2002); https://doi.org/10.1006/exer.2002.2012.
  3. A. Volonterio, C. Ramirez de Arellano and M. Zanda, J. Org. Chem., 70, 2161 (2005); https://doi.org/10.1021/jo0480848.
  4. T. Kohler, G. Friedrich and P. Nuhn, Inflamm. Res., 32, 70 (1991); https://doi.org/10.1007/BF01983315.
  5. F.K. Krichner, J.H. Bailey and C. Cavallito, J. Am. Chem. Soc., 71, 1210 (1949); https://doi.org/10.1021/ja01172a020.
  6. H. Takayanagi, Y. Kitano, T. Yano, H. Umeki and H. Hara, Can. Patent Appl. 2,114,333 (1994).
  7. S.J. Gharpure and S.R.B. Reddy, Org. Lett., 11, 2519 (2009); https://doi.org/10.1021/ol900721q.
  8. A.K. Atta and T. Pathak, Eur. J. Org. Chem., 2010, 6810 (2010); https://doi.org/10.1002/ejoc.201000941.
  9. M.M. El-Mobayed, A.M. Hassein and W.M. Mohlhel, J. Heterocycl. Chem., 47, 534 (2010); https://doi.org/10.1002/jhet.357.
  10. K.K. Jha and Y. Kumer, Asian J. Chem., 21, 6491 (2009).
  11. M.A. El-Hashash, S.A. Rizk and M.M. Aburzeza, Egypt. J. Chem., 54, 1 (2011).
  12. S.A. Rizk and M.A. El-Hashash, Egypt. J. Chem., 54, 5 (2011).
  13. S.A. Rizk, M.A. EL-Hashash and M.M. Aburzeza, Egypt. J. Chem., 54, 3 (2011).
  14. M.A. El-Hashash, G.A. Abdel-Mageid, S.S. El-Kady and S.A. Rizk, Egypt. J. Chem., 51, 103 (2008).
  15. S.A. Rizk, M.A. El-Hashash and K.K. Mostafa, Egypt. J. Chem., 51, 116 (2008).
  16. A.S. Youssef, H.F. Madkour, M.I. Marzouk, A.M. El-Soll and M.A. El-Hashash, Afinidad, 61, 304 (2003).
  17. A.S. Youssef, H.F. Madkour, M.I. Marzouk, A.M. El-Soll and M.A. El-Hashash, Can. J. Chem., 83, 251 (2005); https://doi.org/10.1139/v05-045.
  18. M. Upreti, S. Pant, A. Dandia and U.C. Pant, Phosphorus Sulfur Silicon Rel. Elem., 113, 165 (1996); https://doi.org/10.1080/10426509608046387.
  19. R.D. Khachikyan, N.V. Karamyan, G.A. Panosyan and M.G. Indzhikyan, IZV. Akad. Nauk. Ser. Khim., 1923 (2005).