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

Year 2017, Volume: 4 Issue: 2, 481 - 488, 06.03.2017

Sarra Sıbous Said Boukhrıs Rachida Ghaılane Nouzha Habbadı Amina Hassıkou Abdelaziz Souızı

https://doi.org/10.18596/jotcsa.286900

Cited By: 4

Abstract

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.

Keywords

Heterogeneous catalysts, MAP, DAP, TSP, 3, 4-dihydropyrimidin-2(1H)-ones

References

• 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.