Araştırma Makalesi
BibTex RIS Kaynak Göster
Yıl 2017, Cilt: 4 Sayı: 2, 481 - 488, 06.03.2017
https://doi.org/10.18596/jotcsa.286900

Öz

Kaynakça

  • 1. Lal J, Gupta SK, Thavaselvam D, Agarwal DD. Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3, 4-dihydropyrimidinones of curcumin. Bioorg Med Chem Lett. 2012;22(8):2872–2876.
  • 2. Wan J-P, Pan Y. Recent advance in the pharmacology of dihydropyrimidinone. Mini Rev Med Chem. 2012;12(4):337–349.
  • 3. Wan J-P, Liu Y. Synthesis of dihydropyrimidinones and thiones by multicomponent reactions: strategies beyond the classical Biginelli reaction. Synthesis. 2010;2010(23):3943–3953.
  • 4. Narahari SR, Reguri BR, Gudaparthi O, Mukkanti K. Synthesis of dihydropyrimidinones via Biginelli multi-component reaction. Tetrahedron Lett. 2012;53(13):1543–1545.
  • 5. Japp FR, Klingemann F. I.—Ethylic phenanthroxylene-acetoacetate. J Chem Soc Trans. 1891;59(0):1–26.
  • 6. Zhang Y, Wang B, Zhang X, Huang J, Liu C. An efficient synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones and thiones catalyzed by a novel Brønsted acidic ionic liquid under solvent-free conditions. Molecules. 2015;20(3):3811–3820.
  • 7. Kolvari E, Koukabi N, Armandpour O. A simple and efficient synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones via Biginelli reaction catalyzed by nanomagnetic-supported sulfonic acid. Tetrahedron. 2014;70(6):1383–1386.
  • 8. Starcevich JT, Laughlin TJ, Mohan RS. Iron(III) tosylate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction. Tetrahedron Lett. 2013 Feb;54(8):983–5.
  • 9. Siddiqui ZN. Bis [(L) prolinato-N, O] Zn–water: A green catalytic system for the synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones via the Biginelli reaction. Comptes Rendus Chim. 2013;16(2):183–188.
  • 10. Karthikeyan P, Aswar SA, Muskawar PN, Bhagat PR, Kumar SS. Development and efficient 1-glycyl-3-methyl imidazolium chloride–copper (II) complex catalyzed highly enantioselective synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. J Organomet Chem. 2013;723:154–162.
  • 11. Bahammou I, Esaady A, Boukhris S, Ghailane R, Habbadi N, Hassikou A, et al. Direct use of mineral fertilizers MAP, DAP, and TSP as heterogeneous catalysts in organic reactions. Mediterr J Chem. 2016;5(6):615–623.
  • 12. Nasr-Esfahani M, Taei M. Aluminatesulfonic acid nanoparticles: synthesis, characterization and application as a new and recyclable nanocatalyst for the Biginelli and Biginelli-like condensations. RSC Adv. 2015;5(56):44978–44989.
  • 13. Jetti SR, Bhatewara A, Kadre T, Jain S. Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions. Chin Chem Lett. 2014;25(3):469–473.
  • 14. Zhao Y, Zhao Y, Zhang J, Liu H, Liang L. Polyphosphoric acid catalyst for the one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones by grinding under solvent-free conditions. Indian J Chem. 2015;54:139–141.
  • 15. 1883 - AASR-2012-4-2-988-993.pdf [Internet]. [cited 2017 Jan 19]. Available from: http://s3.amazonaws.com/academia.edu.documents/31197657/AASR-2012-4-2-988-993.pdf?AWSAccessKeyId=AKIAJ56TQJRTWSMTNPEA&Expires=1484852299&Signature=p9ui5dBBpphVSBZpuS6vv4csihc%3D&response-content-disposition=inline%3B%20filename%3DGreen_protocol_for_the_synthesis_of_3_4-.pdf
  • 16. Elhamifar D, Nazari E. Preparation of Iron-Containing Schiff Base and Ionic Liquid Based Bifunctional Periodic Mesoporous Organosilica and Its Application in the Synthesis of 3,4-Dihydropyrimidinones. ChemPlusChem. 2015 May;80(5):820–6.
  • 17. Wang J, Li N, Qiu R, Zhang X, Xu X, Yin S-F. Air-stable zirconocene bis (perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of N-heterocyclic compounds. J Organomet Chem. 2015;785:61–67.
  • 18. Sarrafi Y, Pazokie F, Azizi SN, Alimohammadi K, Mehrasbi E, Chiani E. Mesoporous SBA-15 nanoparticles: An efficient and eco-friendly Catalyst for one-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions. Curr Chem Lett. 2014;3(2):97–102.
  • 19. 1883 - zotero://attachment/100/ [Internet]. [cited 2017 Jan 19]. Available from: zotero://attachment/100/
  • 20. Su W, Li J, Zheng Z, Shen Y. One-pot synthesis of dihydropyrimidiones catalyzed by strontium (II) triflate under solvent-free conditions. Tetrahedron Lett. 2005;46(36):6037–6040.

EASY SYNTHESIS OF 3,4-DIHYDROPYRIMIDIN -2-(1H)-ONES USING PHOSPHATE FERTILIZERS MAP, DAP AND TSP AS EFFICIENT CATALYSTS

Yıl 2017, Cilt: 4 Sayı: 2, 481 - 488, 06.03.2017
https://doi.org/10.18596/jotcsa.286900

Öz

A simple,
efficient and green procedure has been developed for the synthesis of
dihydropyrimidinones (Products of Biginelli) using phosphate fertilizers (mono-ammonium
phosphate (MAP), di-ammonium phosphate (DAP) and triple super phosphate (TSP))
as catalyst. The one-step reaction involved the three compounds, which are
registered aromatic aldehydes, dicarbonyl compounds and the urea/thiourea. This
new method provides some advantages such as obtaining excellent yields (98%),
as well as the short duration of the reaction, which may attain 2 min. These
catalytic heterogeneous systems present also the advantage of being easily
recycled.

Kaynakça

  • 1. Lal J, Gupta SK, Thavaselvam D, Agarwal DD. Design, synthesis, synergistic antimicrobial activity and cytotoxicity of 4-aryl substituted 3, 4-dihydropyrimidinones of curcumin. Bioorg Med Chem Lett. 2012;22(8):2872–2876.
  • 2. Wan J-P, Pan Y. Recent advance in the pharmacology of dihydropyrimidinone. Mini Rev Med Chem. 2012;12(4):337–349.
  • 3. Wan J-P, Liu Y. Synthesis of dihydropyrimidinones and thiones by multicomponent reactions: strategies beyond the classical Biginelli reaction. Synthesis. 2010;2010(23):3943–3953.
  • 4. Narahari SR, Reguri BR, Gudaparthi O, Mukkanti K. Synthesis of dihydropyrimidinones via Biginelli multi-component reaction. Tetrahedron Lett. 2012;53(13):1543–1545.
  • 5. Japp FR, Klingemann F. I.—Ethylic phenanthroxylene-acetoacetate. J Chem Soc Trans. 1891;59(0):1–26.
  • 6. Zhang Y, Wang B, Zhang X, Huang J, Liu C. An efficient synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones and thiones catalyzed by a novel Brønsted acidic ionic liquid under solvent-free conditions. Molecules. 2015;20(3):3811–3820.
  • 7. Kolvari E, Koukabi N, Armandpour O. A simple and efficient synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones via Biginelli reaction catalyzed by nanomagnetic-supported sulfonic acid. Tetrahedron. 2014;70(6):1383–1386.
  • 8. Starcevich JT, Laughlin TJ, Mohan RS. Iron(III) tosylate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction. Tetrahedron Lett. 2013 Feb;54(8):983–5.
  • 9. Siddiqui ZN. Bis [(L) prolinato-N, O] Zn–water: A green catalytic system for the synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones via the Biginelli reaction. Comptes Rendus Chim. 2013;16(2):183–188.
  • 10. Karthikeyan P, Aswar SA, Muskawar PN, Bhagat PR, Kumar SS. Development and efficient 1-glycyl-3-methyl imidazolium chloride–copper (II) complex catalyzed highly enantioselective synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones. J Organomet Chem. 2013;723:154–162.
  • 11. Bahammou I, Esaady A, Boukhris S, Ghailane R, Habbadi N, Hassikou A, et al. Direct use of mineral fertilizers MAP, DAP, and TSP as heterogeneous catalysts in organic reactions. Mediterr J Chem. 2016;5(6):615–623.
  • 12. Nasr-Esfahani M, Taei M. Aluminatesulfonic acid nanoparticles: synthesis, characterization and application as a new and recyclable nanocatalyst for the Biginelli and Biginelli-like condensations. RSC Adv. 2015;5(56):44978–44989.
  • 13. Jetti SR, Bhatewara A, Kadre T, Jain S. Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions. Chin Chem Lett. 2014;25(3):469–473.
  • 14. Zhao Y, Zhao Y, Zhang J, Liu H, Liang L. Polyphosphoric acid catalyst for the one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones by grinding under solvent-free conditions. Indian J Chem. 2015;54:139–141.
  • 15. 1883 - AASR-2012-4-2-988-993.pdf [Internet]. [cited 2017 Jan 19]. Available from: http://s3.amazonaws.com/academia.edu.documents/31197657/AASR-2012-4-2-988-993.pdf?AWSAccessKeyId=AKIAJ56TQJRTWSMTNPEA&Expires=1484852299&Signature=p9ui5dBBpphVSBZpuS6vv4csihc%3D&response-content-disposition=inline%3B%20filename%3DGreen_protocol_for_the_synthesis_of_3_4-.pdf
  • 16. Elhamifar D, Nazari E. Preparation of Iron-Containing Schiff Base and Ionic Liquid Based Bifunctional Periodic Mesoporous Organosilica and Its Application in the Synthesis of 3,4-Dihydropyrimidinones. ChemPlusChem. 2015 May;80(5):820–6.
  • 17. Wang J, Li N, Qiu R, Zhang X, Xu X, Yin S-F. Air-stable zirconocene bis (perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of N-heterocyclic compounds. J Organomet Chem. 2015;785:61–67.
  • 18. Sarrafi Y, Pazokie F, Azizi SN, Alimohammadi K, Mehrasbi E, Chiani E. Mesoporous SBA-15 nanoparticles: An efficient and eco-friendly Catalyst for one-pot synthesis of 3, 4-dihydropyrimidin-2(1H)-ones under solvent-free conditions. Curr Chem Lett. 2014;3(2):97–102.
  • 19. 1883 - zotero://attachment/100/ [Internet]. [cited 2017 Jan 19]. Available from: zotero://attachment/100/
  • 20. Su W, Li J, Zheng Z, Shen Y. One-pot synthesis of dihydropyrimidiones catalyzed by strontium (II) triflate under solvent-free conditions. Tetrahedron Lett. 2005;46(36):6037–6040.
Toplam 20 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Elektrokimya
Bölüm Makaleler
Yazarlar

Sarra Sıbous Bu kişi benim

Said Boukhrıs

Rachida Ghaılane Bu kişi benim

Nouzha Habbadı Bu kişi benim

Amina Hassıkou Bu kişi benim

Abdelaziz Souızı

Yayımlanma Tarihi 6 Mart 2017
Gönderilme Tarihi 21 Ocak 2017
Kabul Tarihi 6 Mart 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 4 Sayı: 2

Kaynak Göster

Vancouver Sıbous S, Boukhrıs S, Ghaılane R, Habbadı N, Hassıkou A, Souızı A. EASY SYNTHESIS OF 3,4-DIHYDROPYRIMIDIN -2-(1H)-ONES USING PHOSPHATE FERTILIZERS MAP, DAP AND TSP AS EFFICIENT CATALYSTS. JOTCSA. 2017;4(2):481-8.