Sulfuric Acid Functionalized Silica-Coated Magnetic Nanoparticles: Preparation and Application in Synthesis of Mono-, Di- and Tri[bis(6-aminopyrimidinyl)methanes]

Abstract

Sulfuric acid functionalized silica-coated magnetic nanoparticles (SSA-MNPs) were prepared by a simple method and evaluated as efficient catalysts for the condensation reaction of 6-amino-1,3-dimethyluracil with mono-, di-, or trialdehydes to give the corresponding mono-, di- and tri[bis(6-aminopyrimidinyl)methanes]. The catalyst was simply recycled by the use of an external magnetic field and could be reused five times without significant loss of activity or mass.

Key words

nanostructures - catalysis - condensation - aldehydes - heterocycles - ultrasound

• References

• 1 Zolfigol MA. Tetrahedron 2001; 57: 9509
• 2 Salehi P, Zolfigol MA, Shirini F, Baghbanzadeh M. Curr. Org. Chem. 2006; 10: 2171
• 3 Gill CS, Price BA, Jones CW. J. Catal. 2007; 251: 145
• 4 Kooti M, Afshari M. Mater. Res. Bull. 2012; 47: 3473
• 5 Sheykhan M, Ma’mani L, Ebrahimi A, Heydari A. J. Mol. Catal. A: Chem. 2011; 335: 253
• 6 Kassaee MZ, Masrouri H, Movahedi F. Appl. Catal., A 2011; 395: 28
• 7 Rostamnia S, Lamei K, Mohammadquli M, Sheykhan M, Heydari A. Tetrahedron Lett. 2012; 53: 5257
• 8a Hirota K, Kuki H, Maki Y. Heterocycles 1994; 37: 563
• 8b Griengl H, Wanek E, Schwarz W, Streicher W, Rosenwirth B, De Clercq E. J. Med. Chem. 1987; 30: 1199
• 8c Srivastava P, Saxena AS, Ram VJ. Synthesis 2000; 541
• 8d Mitsuya H, Yarchoan R, Broder S. Science (Washington D. C.) 1990; 249: 1533
• 8e Pontikis R, Monneret C. Tetrahedron Lett. 1994; 35: 4351
• 8f Wamhoff H, Schupp W. J. Org. Chem. 1986; 51: 2787
• 8g Walsh EB, Wamhoff H. Chem. Ber. 1989; 122: 1673
• 9a Lunt E, Newton CG In Comprehensive Heterocyclic Chemistry . Vol. 3. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 199
• 9b Bradshaw TK, Hutchinson DW. Chem. Soc. Rev. 1977; 6: 43
• 10a Zhi C, Long Z.-Y, Gambino J, Xu W.-C, Brown NC, Barnes M, Butler M, LaMarr W, Wright GE. J. Med. Chem. 2003; 46: 2731
• 10b Devi I, Bhuyan PJ. Tetrahedron Lett. 2005; 46: 5727
• 11a Kappe CO. Tetrahedron 1993; 49: 6937
• 11b Ibrahim DA, El-Metwally AM. Eur. J. Med. Chem. 2010; 45: 1158
• 11c Deshmukh MB, Salunkhe SM, Patil DR, Anbhule PV. Eur. J. Med. Chem. 2009; 44: 2651
• 12 Singh K, Singh S, Mahajan A. J. Org. Chem. 2005; 70: 6114
• 13 Petricci E, Radi M, Corelli F, Botta M. Tetrahedron Lett. 2003; 44: 9181
• 14 Makarov VA, Riabova OB, Granik VG, Dahse H.-M, Stelzner A, Wutzlerc P, Schmidtke M. Bioorg. Med. Chem. Lett. 2005; 15: 37
• 15 Azizian J, Mohammadizadeh MR, Teimouri F, Mohammadi AA, Karimi AR. Synth. Commun. 2006; 23: 3631
• 16 Blotny G. Tetrahedron 2006; 62: 9507
• 17 Bock HR, Anderson S, Fujita Y, Hudson AJ, Rorison JM, Weaver MS. US 6437123, 2002
• 18 Shu W, Valiyaveettil S. Chem. Commun. (Cambridge) 2002; 1350
• 19 Holst HC, Pakula T, Meier H. Tetrahedron 2004; 60: 6765
• 20 Xu F, Wang Z, Gong Q. Opt. Mater. (Amsterdam, Neth.) 2007; 29: 723
• 21 Mooibroek TJ, Gamez P. Inorg. Chim. Acta 2007; 360: 381
• 22a Karimi AR, Alimohammadi Z, Amini MM. Mol. Diversity 2010; 14: 635
• 22b Karimi AR, Alimohammadi Z, Azizian J, Mohammadi AA, Mohammadizadeh MR. Catal. Commun. 2006; 7: 728
• 22c Karimi AR, Pashazadeh R. Synthesis 2010; 437
• 23a Peng ZG, Hidajat K, Uddin MS. J. Colloid Interface Sci. 2004; 271: 277
• 23b Chen FH, Gao Q, Ni JZ. Nanotechnology 2008; 19: 165103
• 24 Tsukimura K, Sasaki S, Kimizuka N. Jpn. J. Appl. Phys. 1997; 36: 3609
• 25 Ghosh S, Badruddoza AZ. M, Uddin MS. J. Colloid Interface Sci. 2011; 354: 483
• 26 Tahmassebi DC, Sasaki T. J. Org. Chem. 1994; 59: 679