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Year 2015, Volume: 4 Issue: 1, 21 - 25, 19.02.2015
https://doi.org/10.17798/beufen.03741

Abstract

In this study, substituted 4-methylcoumarin derivates were synthesized in the presence of sulfuric acid as a catalyst via Pechmann condensation reaction starting from substituted phenol and ethyl acetoacetate. The synthesized compounds were purified through crystallization and characterized with FT-IR, 1H-NMR and 13CNMR, respectively

References

  • Kaynaklar
  • Nachiket Dighe, Shashikant Pattan, Santosh Dengale, Deepak Musmade, Madhuri Shelar, Vishal Tambe1 and Mangesh B Hole. 2010. Synthetic and pharmacological profiles of coumarins, Scholars Research Library Archives of Applied Science Research, 2 , 65-71.
  • Sethna M., Shah M.1945. The Chemstry of Coumarin., Chemical Reviews 36, 1-62.
  • Coffey S., Rood S.1977. Chemistry of Carbon Compounds, Tetrahedron letters 21, 1197-1200
  • Masoud M., Faranak NPolyvinylpolypyrrolidone-bound boron trifluoride (PVPP-BF3).2012 a mild and efficient catalyst for synthesis of 4-metyl coumarins via the Pechmann reaction, Comptes Rendus Chimie 15, 530-532.
  • Bailey G.C., Boettner, F.1921. Production of coumarins from maleic and malic acids. Journal of Industrial and Engineering Chemistry. 13, 905-906.
  • Perkin, W.H.1868. On the artificial production of coumarin and formation of its homologues. Journal of the Chemical Society, Transactions. 21, 53-63.
  • E.Giles., M.P.Poulou., M.Karanis., A.Varagianis.2003. Analtica Chimica Acta.
  • Topkaya taşkıran D., Alp S.2010. Kumarin türevlerinin sentezleri,karakterizasyonları ve sensör uygulamaları. Doktora Tezi, Dokuz Eylül Üniversitesi Fen Bilimleri Enstitüsü.
  • Maria E., Riveiro albertina M., Ramiro V., Natalia G., Graciela F., Lidia P., Emilio Rubin C, Carina S., Carlos D.2008. Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. Bioorganic & Medicinal Chemistry 16, 2665–2675.
  • Inoue Y., Kondo H., Taguchi M., Jinbo Y., Sakamoto F., Tsukamoto G.J.1994. Synthesis and antibacterial activity of thiazolopyrazine-incorporated tetracyclic quinolone antibacterials. J. Med. Chem. 37, 586-592.
  • Ivezic Z., Trkovnik M.2000. Synthesis of some new coumarin-quinolone carboxylic acid journal of heterocylıc chemıstry. 37, 137-141.
  • Kempen I., Papapostolou D., Thierry N., Pochet L., Counerotte S., Masereel B., Foidart J.-M., Reboud-Ravaux M., Noel A., Pirotte B.2003. 3-Bromophenyl 6- acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo. British Journal of Cancer. 88, 1111-1118.
  • Manolov I.D 2003. Synthesis and pharmacological investigations of some 4- hydroxycoumarin derivatives. Arch. Pharm. 336, 83p.
  • Hoult J.R.S., Paya M.1996. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. General Pharmacology. 27, 713-722.
  • Daryoush Z., Mahshad SerehnehD.2014.Recyclable CMK-5 supported sulfonic acid as an environmentallybenign catalyst for solvent-free one-pot construction of coumarinthrough Pechmann condensation, Journal of Molecular Catalysis A: Chemical 391 , 88–91.
  • Meuly, W.C., Kirk-Othmer .1979. Encyclopedia of Chemical Technology, Wiley Interscience Publishers 7,1157-1160.
  • Abdel-Mottaleb M.S.A., Antonious M.S., Abo-Aly M.M., Ismaiel L.F.M., El- Sayed, B.A., Sherief, A.M.K..1989. Photophysics and dynamics of rigidized coumarin laser dyes. Journal of Photochemistry and Photobiology, A: Chemistry. 50, 259-273.
  • Mora A.,Paya,M., J.L., Alcaraz, M.J.1990.Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of nonenzymic lipid peroxidation. Biochemical Pharmacology. 40, 793-797.

Sübstitüe 4-Metilkumarinlerin Sentezi ve Karakterizasyonu

Year 2015, Volume: 4 Issue: 1, 21 - 25, 19.02.2015
https://doi.org/10.17798/beufen.03741

Abstract

Bu çalışmada sübstitüe 4-metilkumarin türevleri   bileşik sentezlendi. Sübstitüe 4-metilkumarin sentezi için sübstitüe fenol ve etil asetoasetat maddelerinden çıkarak iyi bir verimle kumarin eldesini mümkün kılan pechmann yöntemi seçildi. Katalizör olarak sülfürik asit kullanıldı. Elde edilen bileşikler kristallendirme yöntemi ile saflaştırılıp yapıları IR, 1H-NMR ve 13C-NMR gibi spektroskopik yöntemlerle aydınlatıldı.

 

References

  • Kaynaklar
  • Nachiket Dighe, Shashikant Pattan, Santosh Dengale, Deepak Musmade, Madhuri Shelar, Vishal Tambe1 and Mangesh B Hole. 2010. Synthetic and pharmacological profiles of coumarins, Scholars Research Library Archives of Applied Science Research, 2 , 65-71.
  • Sethna M., Shah M.1945. The Chemstry of Coumarin., Chemical Reviews 36, 1-62.
  • Coffey S., Rood S.1977. Chemistry of Carbon Compounds, Tetrahedron letters 21, 1197-1200
  • Masoud M., Faranak NPolyvinylpolypyrrolidone-bound boron trifluoride (PVPP-BF3).2012 a mild and efficient catalyst for synthesis of 4-metyl coumarins via the Pechmann reaction, Comptes Rendus Chimie 15, 530-532.
  • Bailey G.C., Boettner, F.1921. Production of coumarins from maleic and malic acids. Journal of Industrial and Engineering Chemistry. 13, 905-906.
  • Perkin, W.H.1868. On the artificial production of coumarin and formation of its homologues. Journal of the Chemical Society, Transactions. 21, 53-63.
  • E.Giles., M.P.Poulou., M.Karanis., A.Varagianis.2003. Analtica Chimica Acta.
  • Topkaya taşkıran D., Alp S.2010. Kumarin türevlerinin sentezleri,karakterizasyonları ve sensör uygulamaları. Doktora Tezi, Dokuz Eylül Üniversitesi Fen Bilimleri Enstitüsü.
  • Maria E., Riveiro albertina M., Ramiro V., Natalia G., Graciela F., Lidia P., Emilio Rubin C, Carina S., Carlos D.2008. Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. Bioorganic & Medicinal Chemistry 16, 2665–2675.
  • Inoue Y., Kondo H., Taguchi M., Jinbo Y., Sakamoto F., Tsukamoto G.J.1994. Synthesis and antibacterial activity of thiazolopyrazine-incorporated tetracyclic quinolone antibacterials. J. Med. Chem. 37, 586-592.
  • Ivezic Z., Trkovnik M.2000. Synthesis of some new coumarin-quinolone carboxylic acid journal of heterocylıc chemıstry. 37, 137-141.
  • Kempen I., Papapostolou D., Thierry N., Pochet L., Counerotte S., Masereel B., Foidart J.-M., Reboud-Ravaux M., Noel A., Pirotte B.2003. 3-Bromophenyl 6- acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate inhibits cancer cell invasion in vitro and tumour growth in vivo. British Journal of Cancer. 88, 1111-1118.
  • Manolov I.D 2003. Synthesis and pharmacological investigations of some 4- hydroxycoumarin derivatives. Arch. Pharm. 336, 83p.
  • Hoult J.R.S., Paya M.1996. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. General Pharmacology. 27, 713-722.
  • Daryoush Z., Mahshad SerehnehD.2014.Recyclable CMK-5 supported sulfonic acid as an environmentallybenign catalyst for solvent-free one-pot construction of coumarinthrough Pechmann condensation, Journal of Molecular Catalysis A: Chemical 391 , 88–91.
  • Meuly, W.C., Kirk-Othmer .1979. Encyclopedia of Chemical Technology, Wiley Interscience Publishers 7,1157-1160.
  • Abdel-Mottaleb M.S.A., Antonious M.S., Abo-Aly M.M., Ismaiel L.F.M., El- Sayed, B.A., Sherief, A.M.K..1989. Photophysics and dynamics of rigidized coumarin laser dyes. Journal of Photochemistry and Photobiology, A: Chemistry. 50, 259-273.
  • Mora A.,Paya,M., J.L., Alcaraz, M.J.1990.Structure-activity relationships of polymethoxyflavones and other flavonoids as inhibitors of nonenzymic lipid peroxidation. Biochemical Pharmacology. 40, 793-797.
There are 19 citations in total.

Details

Primary Language Turkish
Journal Section Articles
Authors

Kamiran Saraç

Kamiran Saraç

Publication Date February 19, 2015
Submission Date February 19, 2015
Published in Issue Year 2015 Volume: 4 Issue: 1

Cite

IEEE K. Saraç and K. Saraç, “Sübstitüe 4-Metilkumarinlerin Sentezi ve Karakterizasyonu”, Bitlis Eren Üniversitesi Fen Bilimleri Dergisi, vol. 4, no. 1, pp. 21–25, 2015, doi: 10.17798/beufen.03741.

Cited By

4-Klorometil-6-etoksikumarin bileşiğinin deneysel ve kuantum kimyasal hesaplamaları
Anadolu Üniversitesi Bilim Ve Teknoloji Dergisi - B Teorik Bilimler
Kamuran Saraç
https://doi.org/10.20290/aubtdb.294169

Bitlis Eren University
Journal of Science Editor
Bitlis Eren University Graduate Institute
Bes Minare Mah. Ahmet Eren Bulvari, Merkez Kampus, 13000 BITLIS