Synthesis of Novel Proponohydrazides and Their Hydrolysis Reactions

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.

Synthesis of Novel Proponohydrazides and Their Hydrolysis Reactions

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.

___

  • Y. Ak¸camur, A. S¸ener, A.M. Ipeko˘glu and G. Kollenz, J. Heterocyclic Chem. 34, 221-224 (1997).
  • 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).
  • 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).
  • G. Kollenz and W. Heilmayer, Trends in Heterocycl Chem. 3, 379-395 (1993).
  • G. Kollenz, H. Igel and E. Ziegler, Synthesis 11, 679-682 (1972).
  • G. Kollenz, H. Igel and E. Ziegler, Monatsch. Chem. 103, 450-459 (1972).
  • E. Ziegler, G. Kollenz, G. Kriwetz and W. Ott, Liebigs Ann. Chem. 12, 1751-1757 (1977).
  • E. Ziegler, G. Kollenz and W. Ott, Synthesis 11, 679-680 (1973).
  • L. Capuano, S. Drescher and V. Huch, Liebigs Ann. Chem. 331-334 (1991).
  • J. Cossy, D. Belotti, A. Thellend and J.P. Pete, Synthesis 720-721 (1988).
  • C. Kaneko, M. Sato, J. Sakaki and Y. Abe, J. Heterocyclic Chem. 27, 25-30 (1990).
  • B. Freiermuth and C. Wentrup, J. Org. Chem. 56, 2286-2289 (1991).
  • Y. Andreichikov, G. Kollenz, C.O. Kappe, R.L. Toung and C. Wentrup, Acta Chem., Scand. 46, 683-685 (1992).
  • G. Bengtson, S. Keyaniyan and A.D. Mejere, Chem. Ber. 119, 3607-3630 (1986).
  • 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).
  • T.T. Tidwell, Ketenes, John Wiley & Sons, Inc., New York, Chapter, 4.6.1, 227-254 (1995).
  • C. Wentrup, W. Heilmayer and G. Kollenz, Synthesis 1219-1248 (1994).
  • A.D. Allen, J. Andraos, A.S. Kreske, M.A. McAllister and T.T. Tidwell., J. Am. Chem. Soc. 114, 1878-1879 (1992).
  • B.C. Wallfisch, F. Belaj, C. Wentrup, C.O. Kappe and G. Kollenz, J. Chem. Soc. Perkin Trans. 1, 599-605 (2002).
  • A.G. Birchler, F. Liuand and L.S. Liebeskind, J. Org. Chem. 59, 7737-7740 (1994).
  • C.O. Kappe, G. Farber, C. Wentrup and G. Kollenz, Tetrahedron Lett. 33, 4553-4556 (1992).
  • A. Stadler, K. Zangger, F. Belaj and G. Kollenz, Tetrahedron. 57, 6757-6763 (2001).
  • C.O. Kappe, G. Farber, C. Wentrup and G. Kollenz, J. Org. Chem. 57, 7078-7083 (1992).
  • D. Zimmermann, Y.L. Janin, L. Brehm, H.B. Osborne, B. Ebert, T.N. Johansen, U. Madsen and P.K. Larsen, Eur. J. Med. Chem. 34, 967-976 (1999).
  • M.J. Laufersweiler, T.A. Brugel, M.P. Clark, A. Golebiowski, R.G. Bookland, S.K. Laughlin, M.P. Sabat and J.A. Townes, Bioorg. Med. Chem. Lett. 14, 4267-4272 (2004).
  • J. Sokolowska, D. Hinks and H.S. Freeman, Dyes and Pigments 48, 15-27 (2001).
  • D.G. Schmidt and H. Zimmer, J. Org. Chem. 48, 4367-4370 (1983).
  • D. ¨Ulk¨u, C. Arıcı, F. Ercan, M. Sa¸cmacı, E. Sarıpınar and Y. Ak¸camur, Z. Kristallogr. 218, 377-380 (2003).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Synthesis of isomorphous prototypic $[CrFe_2O(AcO)_6(TEP)_3]Cl$ and $[CrFe_2O(AcO_6(TMP)_3]Cl$ As Oxo-centered hetero tri-nuclear carboxylate complexes

Massoud RAFIZADEH, Vahid AMANI, Reza TAYEBEE

Phlinoside F, a New Phenylethanoid Glycoside from Phlomis angustissima

Funda Nuray YALÇIN, Tayfun ERSÖZ, Erdal BEDİR, Sevser ŞAHPAZ, François BAILLEUL, İkhlas A. KHAN, Ali A. DÖNMEZ, İhsan ÇALIŞ

Anodic Stripping Voltammetric Behavior of Mercury in Chloride Medium and its Determination at a Gold Film Electrode

Füsun OKÇU, F. Nil ERTAŞ, H. İsmet GÖKÇEL, Hüseyin TURAL

Some New Mannich Bases of 5-Methyl-2-Benzoxazolinones With Analgesis and Anti-Inflammatory Activities

Nesrin GÖKHAN, Meriç KÖKSAL, Esra KÜPELİ

Synthesis of Isomorphous Prototypic [CrFe2O(AcO)6(TEP)3]Cl and [CrFe2O(AcO)6(TMP)3]Cl As Oxo-Centered Hetero Tri-Nuclear Carboxylate Complexes

Massoud RAFIZADEH, Reza TAYEBEE, Vahid AMANI

Synthesis of Novel Proponohydrazides and Their Hydrolysis Reactions

Mustafa SAÇMACI, Emin Saripinar And Yunus AKÇAMUR, Emin SARIPINAR, Yunus AKÇAMUR

Studies on Mononuclear Chelates Derived from Substituted Schiff Base Ligands (Part 4): Synthesis and Characterization of a New 5-Hydroxysalicyliden-P-Aminoacetophenoneoxime and Its Complexes with Co(II), Ni(II), Cu(II) and Zn(II)

Erdal CANPOLAT, Mehmet KAYA

Synthesis of Mannich Bases of Some 2,5-Disubstituted 4-Thiazolidinones and Evaluation of Their Antimicrobial Activities

Handan ALTINTAŞ, Öznur ATEŞ, Seher BİRTEKSÖZ, Gülten ÖTÜK

Design and Characterization of Amino and Chloro Functionalized Rhombohedral Silsesquioxanes

Ahmet GÜLTEK, Turgay SEÇKİN, Halil İbrahim ADIGÜZEL

Proton conduction in PVPA-benzimidazole hybrid electrolytes

Ayhan BOZKURT, Fatma SEVİL