Journals / Turkish Journal of Chemistry / 2015 / Cilt: 39 - Sayı: 2

Ring opening and ring closure reactions of chromone-3-carboxylic acid: unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes

Pages
412
Publication Date
2015-08-13
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Structures of the new synthesized products were established on the basis of elemental analysis and spectral data (IR, MS, and ^1H and ^{13}C NMR).

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes were achieved via transformations of the \gamma-pyrone ring in chromone-3-carboxylic acid throughout its reactions with some acyclic and cyclic carbon nucleophiles.
📊
Key Findings & Data:A key part of the reaction mechanisms is discussed.
💡
Conclusion & Impact:Structures of the new synthesized products were established on the basis of elemental analysis and spectral data (IR, MS, and ^1H and ^{13}C NMR).
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Chromone-3-carboxylic acid · benzoxocinone · pyranochromenes

Abstract

Unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes were achieved via transformations of the \gamma-pyrone ring in chromone-3-carboxylic acid throughout its reactions with some acyclic and cyclic carbon nucleophiles. A key part of the reaction mechanisms is discussed. Structures of the new synthesized products were established on the basis of elemental analysis and spectral data (IR, MS, and ^1H and ^{13}C NMR).

Özet

Unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes were achieved via transformations of the \gamma-pyrone ring in chromone-3-carboxylic acid throughout its reactions with some acyclic and cyclic carbon nucleophiles. A key part of the reaction mechanisms is discussed. Structures of the new synthesized products were established on the basis of elemental analysis and spectral data (IR, MS, and ^1H and ^{13}C NMR).

🔖

Cite This Article

IBRAHIM, M. A., ALI, T. E. (2015). Ring opening and ring closure reactions of chromone-3-carboxylic acid: unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes. Turkish Journal of Chemistry, Cilt: 39 - Sayı: 2, 412. https://ajindex.com/articles/185154

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (29)

  1. Nam, D. H.; Lee, K. Y.; Moon, C. S.; Lee, Y. S. Eur. J. Med. Chem. 2010, 45, 4288–4292.
  2. Raj, T.; Bhatia, R. K.; Kapur, A.; Sharma, M.; Saxena, A. K.; Ishar, M. P. S. Eur. J. Med. Chem. 2010, 45, 790–794.
  3. Ali, T. E.; Ibrahim, M. A. J. Braz. Chem. Soc. 2010, 21, 1007–1016.
  4. Ibrahim, M. A.; Ali, T. E.; Alnamer, Y. A.; Gabr, Y. A. Arkivoc 2010, i, 98–154.
  5. Rocha-Pereira, J.; Cunha, R.; Pinto, D. C. G. A.; Silva, A. M. S.; Nascimento, M. S. J. Bioorg. Med. Chem. 2010, 184, 4195–4201.
  6. Li, Y.; Zhao, Y.; Xiang, N.; Yang, L.; Wang, F.; Yang, G.; Wang, Z. Heterocycles 2014, 89, 2771–2776.
  7. Ghosh, C. K. Heterocycles 2004, 63, 2875–2898.
  8. Plaskon, A. S.; Grygorenko, O. O.; Ryabukhin, S. V. Tetrahedron 2012, 68, 2743–2757.
  9. Sosnovskikh, V. Y.; Irgashev, R. A.; Kodess, M. I. Tetrahedron 2008, 64, 2997–3004.
  10. Budzisz, E.; Miemicka, M.; Lorenz, I. P.; Mayer, P.; Krajewska, U.; Rozalski, M. Polyhedron 2009, 28, 637–645.
  11. Sosnovskikh, V. Y.; Korotaev, V. Y.; Barkov, A. Y.; Sokovnina, A. A.; Kodess, M. I. J. Fluorine Chem. 2012, 141, 58–63.
  12. Sosnovskikh, V. Y.; Sevenard, D. V.; Moshkin, V. S.; Iaroshenko, V. O.; Langer, P. Tetrahedron 2010, 66, 7322– 7328. Sosnovskikh, V. Y.; Safrygin, A. V.; Anufriev, V. A.; Eltsov, O. S.; Iaroshenko, V. O. Tetrahedron Lett. 2011, 52, 6271–6274.
  13. Akbarzadeh, R.; Amanpour, T.; Bazgir A. Tetrahedron 2014, 70, 8142–8147.
  14. Ibrahim, M. A. J. Braz. Chem. Soc. 2013, 24, 1754–1763.
  15. Ibrahim, M. A.; El-Gohary, N. M.; Ibrahim, S. S.; Said S. Chem. Heterocycl. Compds. 2015, 50, 1624–1633.
  16. Ali, T. E.; Abdel-Aziz, S. A.; El-Edfawy, S. M.; Mohamed, E. A.; Abdel-Kariem, S. M. Synth. Commun. 2014, 44, 3610–3629.
  17. Klutchko, S.; Shavel, J.; Strandtmann, M. V. J. Org. Chem. 1974, 39, 2436–2437.
  18. Ghosh, C. K.; Mukhopadhyay, K. K. Synthesis 1978, 10, 779–784.
  19. Chantegrel, B.; Nadi, A., Gelin, S. Tetrahedron Lett. 1983, 24, 381–384.
  20. Chantegrel, B.; Nadi, A.; Gelin, S. J. Org. Chem. 1984, 49, 4419–4424.
  21. Ibrahim, M. A. Arkivoc 2008, xvii, 192–204.
  22. Ali, T. E.; Abdel-Monem, W. R. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 2161–2172.
  23. Ibrahim, M. A. Tetrahedron 2009, 65, 7687–7690.
  24. Ibrahim, M. A. Synth. Commun. 2009, 39, 3527–3545.
  25. Ali, T. E. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 88–96.
  26. Ibrahim, M. A.; Ali, T. E.; El-Kazak, A. M.; Mohamed, A. M. Heterocycles 2013, 87, 1075–1086.
  27. Ibrahim, M. A. Tetrahedron 2013, 69, 6861–6865.
  28. Ibrahim, M. A.; Ali, T. E.; El-Gohary, N. M.; El-Kazak, A. M. Eur. J. Chem. 2013, 4, 311–328.
  29. Ali, T. E.; Abdel-Aziz, S. A.; El-Edfawy,