Journals / Turkish Journal of Chemistry / 2005 / Cilt: 29 - Sayı: 4

Synthesis of Novel Proponohydrazides and Their Hydrolysis Reactions

Pages
401–407
Publication Date
2005-04-01
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)

The structures of these new synthesized compounds were determined by 13C NMR, 1H NMR and IR spectroscopic data and elemental analysis.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:4-(4-Methoxybenzoyl)-5-(4-methoxyphenyl)-2,3-furandione 1 reacted with N-aryl substituted phenylhydrazones 3a-h via the p,p'-dimethoxydibenzoylketene intermediate 2 giving the proponohydrazide derivatives 5a-h.
📊
Key Findings & Data:In addition, compounds 5a-h were converted into corresponding pyrazolone derivatives 7i,j by the reactions of hydrolysis in acidic solution.
💡
Conclusion & Impact:The structures of these new synthesized compounds were determined by 13C NMR, 1H NMR and IR spectroscopic data and elemental analysis.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Furan-2 · 3-dione · Proponohydrazide

Abstract

4-(4-Methoxybenzoyl)-5-(4-methoxyphenyl)-2,3-furandione 1 reacted with N-aryl substituted phenylhydrazones 3a-h via the p,p'-dimethoxydibenzoylketene intermediate 2 giving the proponohydrazide derivatives 5a-h. In addition, compounds 5a-h were converted into corresponding pyrazolone derivatives 7i,j by the reactions of hydrolysis in acidic solution. The structures of these new synthesized compounds were determined by 13C NMR, 1H NMR and IR spectroscopic data and elemental analysis.

Özet

4-(4-Methoxybenzoyl)-5-(4-methoxyphenyl)-2,3-furandione 1 reacted with N-aryl substituted phenylhydrazones 3a-h via the p,p'-dimethoxydibenzoylketene intermediate 2 giving the proponohydrazide derivatives 5a-h. In addition, compounds 5a-h were converted into corresponding pyrazolone derivatives 7i,j by the reactions of hydrolysis in acidic solution. The structures of these new synthesized compounds were determined by 13C NMR, 1H NMR and IR spectroscopic data and elemental analysis.

🔖

Cite This Article

SAÇMACI, M., AKÇAMUR, E. S. A. Y., SARIPINAR, E., AKÇAMUR, Y. (2005). Synthesis of Novel Proponohydrazides and Their Hydrolysis Reactions. Turkish Journal of Chemistry, Cilt: 29 - Sayı: 4, 401–407. https://ajindex.com/articles/382191

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (23)

  1. Y. Ak¸camur, A. S¸ener, A.M. Ipeko˘glu and G. Kollenz, J. Heterocyclic Chem. 34, 221-224 (1997).
  2. G. Kollenz, G. Penn, G. Dolenz, Y. Ak¸camur, K. Peters, E.M. Peters and H.G. von Schnering, Chem. Ber., 1299-1309 (1984). S¸.H. ¨Ung¨oren, M. Sa¸cmacı, Y. Ak¸camur, C. Arıcı and D. ¨Ulk¨u, J. Heterocyclic Chem. 41, 151-155 (2004). A. S¸ener, R. Kasimogulları, M.K. S¸ener, ˙I. Bıldırıcı and Y. Ak¸camur, J. Heterocyclic Chem. 39, 869-875 (2002).
  3. E. Saripinar, Y. Guzel, Z. Onal, I.O. Ilhan and Y. Akcamur, J. Chem. Soc. Pak. 22, 308-317 (2000). T. H¨okelek, E. Sarıpınar, ˙I. Yıldırım, M. Akkurt and Y. Ak¸camur, Acta Cryst. E 58, 30-32 (2002). Y. Ak¸camur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E.M. Peters and H.G. von Schnering, Monatsch. Chem. 117, 231-245 (1986).
  4. G. Kollenz and W. Heilmayer, Trends in Heterocycl Chem. 3, 379-395 (1993).
  5. G. Kollenz, H. Igel and E. Ziegler, Synthesis 11, 679-682 (1972).
  6. G. Kollenz, H. Igel and E. Ziegler, Monatsch. Chem. 103, 450-459 (1972).
  7. E. Ziegler, G. Kollenz, G. Kriwetz and W. Ott, Liebigs Ann. Chem. 12, 1751-1757 (1977).
  8. E. Ziegler, G. Kollenz and W. Ott, Synthesis 11, 679-680 (1973).
  9. L. Capuano, S. Drescher and V. Huch, Liebigs Ann. Chem. 331-334 (1991).
  10. J. Cossy, D. Belotti, A. Thellend and J.P. Pete, Synthesis 720-721 (1988).
  11. C. Kaneko, M. Sato, J. Sakaki and Y. Abe, J. Heterocyclic Chem. 27, 25-30 (1990).
  12. B. Freiermuth and C. Wentrup, J. Org. Chem. 56, 2286-2289 (1991).
  13. Y. Andreichikov, G. Kollenz, C.O. Kappe, R.L. Toung and C. Wentrup, Acta Chem., Scand. 46, 683-685 (1992).
  14. G. Bengtson, S. Keyaniyan and A.D. Mejere, Chem. Ber. 119, 3607-3630 (1986).
  15. J.E. Lynch, S.M. Riseman, W.L. Laswell, D.M. Tschaen, R.P. Volante, B.B. Smith and I. Shinkai, J. Org. Chem. 54, 3792-3796 (1989).
  16. T.T. Tidwell, Ketenes, John Wiley & Sons, Inc., New York, Chapter, 4.6.1, 227-254 (1995).
  17. C. Wentrup, W. Heilmayer and G. Kollenz, Synthesis 1219-1248 (1994).
  18. A.D. Allen, J. Andraos, A.S. Kreske, M.A. McAllister and T.T. Tidwell., J. Am. Chem. Soc. 114, 1878-1879 (1992).
  19. B.C. Wallfisch, F. Belaj, C. Wentrup, C.O. Kappe and G. Kollenz, J. Chem. Soc. Perkin Trans. 1, 599-605 (2002).
  20. A.G. Birchler, F. Liuand and L.S. Liebeskind, J. Org. Chem. 59, 7737-7740 (1994).
  21. C.O. Kappe, G. Farber, C. Wentrup and G. Kollenz, Tetrahedron Lett. 33, 4553-4556 (1992).
  22. A. Stadler, K. Zangger, F. Belaj and G. Kollenz, Tetrahedron. 57, 6757-6763 (2001).
  23. C.O. Kappe, G. Farber, C. Wentrup and G. Kollenz, J. Org. Chem. 57, 7078-7083 (1992). D. Zimmermann,