Zirconium(IV) 4-sulphophenylethyliminobismethylphosphonate as an efficient and reusable catalyst for one-pot synthesis of 3,4-dihydropyrimidones under solvent-free conditions

Chemical Papers - Tập 65 - Trang 829-834 - 2011
Xin-Bin Yang1, Xiang-Kai Fu2, Yu Huang3, Ren-Quan Zeng1
1Department of Chemistry, Rongchang Campus, Southwest University, Chongqing, China
2School of Chemistry and Chemical Engineering, Southwest University, Chongqing, China
3Pharmacy College, Ningxia Medical University, Yinchuan, China

Tóm tắt

Zirconium(IV) 4-sulphophenylethyliminobismethylphosphonate (ZSBEDP) was prepared and characterised by elemental analysis, IR, TG-DSC, and XRD. ZSBEDP was found to be an efficient catalyst for the Biginelli reaction of aromatic aldehyde, ethyl acetoacetate, and urea or thiourea under solvent-free conditions so as to give 3,4-dihydropyrimidones in good to excellent yields. The catalyst can be separated by simple filtration and reused without significant loss of its catalytic activity.

Tài liệu tham khảo

Abdollahi-Alibeik, M., & Zaghaghi, Z. (2009). 1,3-Dibromo-5,5-dimethylhydantoin as a useful reagent for efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions. Chemical Papers, 63, 97–101. DOI: 10.2478/s11696-008-0084-1. Banik, B. K., Reddy, A. T., Datta, A., & Mukhopadhyay, C. (2007). Microwave-induced bismuth nitrate-catalyzed synthesis of dihydropyrimidones via Biginelli condensation under solventless conditions. Tetrahedron Letters, 48, 7392–7394. DOI: 10.1016/j.tetlet.2007.08.007. Clearfield, A., & Thakur, D. S. (1986). Zirconium and titanium phosphates as catalysts: A review. Applied Catalysis, 26, 1–26. DOI: 10.1016/S0166-9834(00)82538-5. Clearfield, A., Wang, J. D., Tian, Y., Stein, E., & Bhardwaj, C. (1995). Synthesis and stability of mixed ligand zirconium phosphonate layered compounds. Journal of Solid State Chemistry, 117, 275–289. DOI: 10.1006/jssc.1995.1274. Costantino, U., Fringuelli, F., Orrů, M., Nocchetti, M., Piermatti, O., & Pizzo, F. (2009). Direct aza-Diels-Alder reaction in water catalyzed by layered α-zirconium hydrogen phosphate and sodium dodecyl sulfate. European Journal of Organic Chemistry, 2009, 1214–1220. DOI: 10.1002/ejoc.200801132. Curini, M., Montanari, F., Rosati, O., Lioy, E., & Margarita, R. (2003). Layered zirconium phosphate and phosphonate as heterogeneous catalyst in the preparation of pyrroles. Tetrahedron Letters, 44, 3923–3925. DOI: 10.1016/s0040-4039(03)00810-4. Dines, M. B., & DiGiacomo, P. M. (1981). Derivatized lamellar phosphates and phosphonates of M(IV) ions. Inorganic Chemistry, 20, 92–97. DOI: 10.1021/ic50215a022. Joseph, J. K., Jain, S. L., & Sain, B. (2006). Ion exchange resins as recyclable and heterogeneous solid acid catalysts for the Biginelli condensation: An improved protocol for the synthesis of 3,4-dihydropyrimidin-2-ones. Journal of Molecular Catalysis A: Chemical, 247, 99–102. DOI: 10.1016/j.molcata.2005.11.028. Kamiya, Y., Sakata, S., Yoshinaga, Y., Ohnishi, R., & Okuhara, T. (2004). Zirconium phosphate with a high surface area as a water-tolerant solid acid. Catalysis Letters, 94, 45–47. DOI: 10.1023/B:CATL.0000019329.82828.e4. Kappe, C. O. (2000). Biologically active dihydropyrimidones of the Biginelli-type — a literature survey. European Journal of Medicinal Chemistry, 35, 1043–1052. DOI: 10.1016/s0223-5234(00)01189-2. Kappe, C. O. (1993). 100 years of the Biginelli dihydropyrimidine synthesis. Tetrahedron, 49, 6937–6963. DOI: 10.1016/S0040-4020(01)87971-0. Kumar, A., & Maurya, R. A. (2008). Organocatalysed threecomponent domino synthesis of 1,4-dihydropyridines under solvent free conditions. Tetrahedron, 64, 3477–3482. DOI: 10.1016/j.tet.2008.02.022. Ma, X. B., & Fu, X., K. (2004). Synthesis of the novel layered amorphous and crystalline zirconium phosphate-phosphonates Zr(HPO4)[O3PCH2N(CH2CH2)2O]·nH2O, Zr(HPO4)[O3PCH2N(CH2CO2H)2]·nH2O, zirconium phosphonates Zr[(O3PCH2)NCH2CO2H]·nH2O and the catalytic activities of their palladium complexes in hydrogenation. Journal of Molecular Catalysis A: Chemical, 208, 129–133. DOI: 10.1016/j.molcata.2003.07.004. Moedritzer, K., & Irani, R. R. (1966). The direct synthesis of α-aminomethylphosphonic acids. Mannich-type reactions with orthophosphorous Acid. Journal of Organic Chemistry, 31, 1603–1607. DOI: 10.1021/jo01343a067. Okuhara, T. (2002). Water-tolerant solid acid catalysts. Chemical Reviews, 102, 3641–3666. DOI: 10.1021/cr0103569. Patel, S. M., Chudasama, U. V., & Ganeshpure, P. A. (2001). Metal(IV) phosphates as solid acid catalysts for selective cyclodehydration of 1,n-diols. Green Chemistry, 3, 143–145. DOI: 10.1039/b100503k. Patil, A. D., Kumar, N. V., Kokke, W. C., Bean, M. F., Freyer, A. J., De Brosse, C., Mai, S., Truneh, A., Faulkner, D. J., Carte, B., Breen, A. L., Hertzberg, R. P., Johnson, R. K., Westley, J. W., & Potts, B. C. M. (1995). Novel alkaloids from the sponge Batzella sp.: Inhibitors of HIV gp120-human CD4 binding. The Journal of Organic Chemistry, 60, 1182–1188. DOI: 10.1021/jo00110a021. Peng, J. J., & Deng, Y. Q. (2001). Ionic liquids catalyzed Biginelli reaction under solvent-free conditions. Tetrahedron Letters, 42, 5917–5919. DOI: 10.1016/s0040-4039(01)01139-x. Quan, Z.-J., Da, Y.-X., Zhang, Z., & Wang, X.-C. (2009). PS-PEG-SO3H as an efficient catalyst for 3,4-dihydropyrimidones via Biginelli reaction. Catalysis Communications, 10, 1146–1148. DOI: 10.1016/j.catcom.2008.12.017. Reddy, B. M., Sreekanth, P. M., & Lakshmanan, P. (2005). Sulfated zirconia as an efficient catalyst for organic synthesis and transformation reactions. Journal of Molecular Catalysis A: Chemical, 237, 93–100. DOI: 10.1016/j.molcata.2005.04.039. Reddy, C. V., Mahesh, M., Raju, P. V. K., Babu, T. R., & Reddy, V. V. N. (2002). Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Letters, 43, 2657–2659. DOI: 10.1016/s0040-4039(02)00280-0. Rovnyak, G. C., Kimball, S. D., Beyer, B., Cucinotta, G., Di-Marco, J. D., Gougoutas, J., Hedberg, A., Malley, M., McCarthy, J. P., Zhang, R., & Moreland, S. (1995). Calcium entry blockers and activators: Conformational and structural determinants of dihydropyrimidine calcium channel modulators. Journal of Medicinal Chemistry, 38, 119–129. DOI: 10.1021/jm00001a017. Yang, Y. J., Liu, C. H., Wu, H. X., & Li, R. (2010). Preparation and characterization of films based on zirconium sulfophenyl phosphonate and chitosan. Carbohydrate Research, 345, 148–153. DOI: 10.1016/j.carres.2009.10.012. Zima, V., Svoboda, J., Melánová, K., Beneš, L., Casciola, M., Sganappa, M., Brus, J., & Trchová, M. (2010). Synthesis and characterization of new zirconium 4-sulfophenylphosphonates. Solid State Ionics, 181, 705–713. DOI: 10.1016/j.ssi.2010. 03.034. Zou, X.-C., Fu, X.-K., Li, Y.-D., Gong, B.-W., Chen, J.-X., & Tu, X.-B. (2009). Synthesis of crystalline layered zirconium phenylethylamino-N,N-bis methylphosphonates and analysis for its novel interlayer distance. Chinese Journal of Inorganic Chemistry, 25, 290–295.