Preparation and characterization of bentonite/PS-SO 3H nanocomposites as an efficient acid catalyst for the Biginelli reaction

Applied Clay Science

Volumn 55, Issue , 2012, Pages 1-9

  Kalbasi, Roozbeh Javad ^a   Massah, Ahmad Reza ^a   Daneshvarnejad, Behnam ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Bentonite; Biginelli reaction; Dihydropyrimidinones; Nanocomposite; Organic inorganic hybrid material

Indexed keywords

ACID CATALYST; BIGINELLI REACTION; DI-HYDROPYRIMIDINONES; ENVIRONMENTALLY BENIGN; HIGH THERMAL STABILITY; ORGANIC-INORGANIC HYBRID MATERIALS; SOLVENT FREE CONDITIONS; XRD;

BENTONITE; HYBRID MATERIALS; NANOCOMPOSITES; REUSABILITY;

CATALYSTS;

BENTONITE; CATALYST; COMPOSITE; FTIR SPECTROSCOPY; SCANNING ELECTRON MICROSCOPY; SOLVENT; THERMOGRAVIMETRY; X-RAY DIFFRACTION;

EID: 84855451925     PISSN: 01691317     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.clay.2011.05.015     Document Type: Article

References (58)

1. Ahmed B., Khan A.R., Keshari M. An improved synthesis of Biginelli-type compounds via phase-transfer catalysis. Tetrahedron Lett. 2009, 50:2889-2892.
2. Atwal K.S., Swanson B.N., Unger S.E., Floyd D.M., Moreland S., Hedberg A., O'Reilly B.C. 3-Carbamoyl-4-aryl-1,2,3,4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents. J. Med. Chem. 1991, 34:806-811.
3. 2O supported on silica gel as a novel heterogeneous system catalyzed biginelli reaction: one-pot synthesis of di-hydropyrimidinones under solvent-free conditions. Appl. Catal., A 2006, 300:85-88.
4. Bigdeli M.A., Jafari S., Mahdavinia G.H., Hazarkhani H. Trichloroisocynuric acid, a new and efficient catalyst for the synthesis of dihydropyrimidinones. Catal. Commun. 2007, 8:1641.
5. Biginelli P. Aldehyde-urea derivatives of aceto- and oxaloacetic acids. Gazz. Chim. Ital. 1893, 23:360-413.
6. Chen X., Peng Y. Chloroferrate(III) ionic liquid: efficient and recyclable catalyst for solvent-free synthesis of 3,4-dihydropyrimidin-2(1H )-ones. Catal. Lett. 2008, 122:310-313.
7. Chitra S., Pandiarajan K. Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction. Tetrahedron Lett. 2009, 50:2222-2224.
8. Ding Y., Guo C., Dong J.Y., Wang Z. Novel organic modification of montmorillonite in hydrocarbon solvent using ionic liquid-type surfactant for the preparation of polyolefin-clay nanocomposites. J. Appl. Polym. Sci. 2006, 102:4314-4320.
9. Folkers K., Johnson T.B. Hydrogenation of cyclic ureides under elevated temperatures and pressures. I.1 2-Keto-1,2,3,4-tetrahydropyrimidines. J. Am. Chem. Soc. 1934, 56:1180-1185.
10. Folkers K., Harwood H.J., Johnson T.B. Researches on pyrimidines. Cxxx. Synthesis of 2-Keto-1,2,3,4-Tetrahydropyrimidines. J. Am. Chem. Soc. 1932, 54:3751-3758.
11. Fu N.Y., Yuan Y.E., Cao Z., Wang S.W., Wang J.T., Peppe C. Indium (III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction. Tetrahedron 2002, 58:4801-4807.
12. Ganguly A., Bhowmick A.K. Sulfonated styrene-(ethylene-co-butylene)-styrene/montmorillonite clay nanocomposites: synthesis, morphology, and properties. Nanoscale Res. Lett. 2008, 1:36-44.
13. 2. Appl. Catal., A 2005, 287:83-88.
14. 2. Appl. Catal., A 2007, 320:35-42.
15. Goss J.M., Schaus S.E. Enantioselective synthesis of SNAP-7941: chiral dihydropyrimidone inhibitor of MCH1-R. J. Org. Chem. 2008, 73:7651-7656.
16. Grover G.J., Dzwonczyk S., McMullen D.M., Normandin D.E., Parham C.S., Sleph P.G., Moreland S. Pharmacologic profile of the dihydropyrimidine calcium channel blockers SQ 32,547 and SQ 32,946. J. Cardiovasc. Pharmacol. 1995, 26:289-294.
17. Heravi M.M., Derikvand F., Bamoharram F.F. A catalyst method for synthesis of Biginelli-type 3,4-dihydropyrimidin-2(1H)-one using 12-tungstophosphoric acid. J. Mol. Catal. A: Chem. 2005, 242:173.
18. Heravi M.M., Bakhtiari Kh., Bamoharram F.F. 12-Molybdophosphoric acid: a recyclable catalyst for synthesis of Biginelli-type 3,4-dihydropyridine-2(1H)-ones. Catal. Commun. 2006, 7:373.
19. 4 immobilized Cu (II) acetylacetonate as recyclable catalytic system. Catal. Lett. 2007, 115:52-55.
20. 4/ZSM-5. Appl. Catal., A 2009, 353:1-8.
21. 2. Bull. Korean Chem. Soc. 2010, 31:2361-2368.
22. 2: using ethyl acetate as a green and efficient acylating agent. Chin. J. Chem. 2010, 28:273-284.
23. 2 using nitric acid. Chin. J. Chem. 2010, 28:397-403.
24. Kalbasi R.J., Massah A.R., Zamani F., Bain A.D., Berno B. Metal (Co, Mn)-amine-functionalized mesoporous silica SBA-15: synthesis, characterization and catalytic properties in hydroxylation of benzene. J. Porous Mater. 2011, 18:475-482.
25. Khabazzadeh H., Saidi K., Sheibani H. Microwave-assisted synthesis of dihydropyrimidin-2(1H)-ones using graphite supported lanthanum chloride as a mild and efficient catalyst. Bioorg. Med. Chem. Lett. 2008, 18:278-280.
26. Khan A.I., O'Hare D. Intercalation chemistry of layered double hydroxides: recent developments and applications. J. Mater. Chem. 2002, 12:3191-3198.
27. Kolosov M.A., Orlov V.D., Beloborodov D.A., Dotsenko V.V. A chemical placebo: NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis. Mol. Divers. 2009, 13:5-25.
28. Kumar A., Maurya R.A. Synthesis of 3,4-dihydropyrimidin-2(1H)-ones using Ziegler-Natta catalyst system under free conditions. J. Mol. Catal. A: Chem. 2007, 272:53.
29. Li P., Wang L., Zhang Y., Wang M. Highly efficient three-component (aldehyde-alkyne-amine) coupling reactions catalyzed by a reusable PS-supported NHC-Ag(I) under solvent-free reaction conditions. Tetrahedron Lett. 2008, 49:6650-6654.
30. Lilja J., Aumo J., Salmi T., Murzin D.Yu., Mäki-Arvela P., Sundell M., Ekman K., Peltonen R., Vainio H. Kinetics of esterification of propanoic acid with methanol over a fibrous polymer-supported sulphonic acid catalyst. Appl. Catal., A 2002, 228:253-267.
31. Litvic M., Vecenaj I., Ladisic Z.M., Lovric M., Vinkovic V., Filipan-Litvic M. First application of hexaaquaaluminium(III) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst in organic synthesis: a simple and efficient protocol for the multigram scale synthesis of 3,4-dihydropyrimidinones by Biginelli reaction. Tetrahedron 2010, 66:3463-3471.
32. Liu X.W., Pasunooti K.K., Chai H., Jensen C.N., Gorityala B.K., Wang S. A microwave-assisted, copper-catalyzed three-component synthesis of dihydropyrimidinones under mild conditions. Tetrahedron Lett. 2011, 52:80.
33. Lopes W.A., Jaege H.M. Hierarchical self-assembly of metal nanostructures on diblock copolymer scaffolds. Nature 2001, 414:735-738.
34. Madejová J. FTIR techniques in clay mineral studies. Vib. Spectrosc. 2003, 31:1-10.
35. Maiti G., Kundu P., Guin C. One-pot synthesis of dihydropyrimidinones catalysed by lithium bromide: an improved procedure for the Biginelli reaction. Tetrahedron Lett. 2003, 44:2757-2758.
36. Massah A.R., Asadi B., Hoseinpour M., Molseghi A., Kalbasi R.j., Javaherian Naghash H. A novel and efficient solvent-free and heterogeneous method for the synthesis of primary, secondary and bis-N-acylsulfonamides using metal hydrogen sulfate catalysts. Tetrahedron 2009, 65:7696-7705.
37. Ming D.W., Dixon J.B. Quantitative determination of clinoptilolite in soils by a cation-exchange capacity method. Clays Clay Miner. 1987, 35:463-468.
38. Newman S.P., Jones W. Synthesis, characterization and applications of layered double hydroxides containing organic guests. New J. Chem. 1998, 22:105-116.
39. Paraskar A.S., Dewkar G.K., Sudalai A. A reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2003, 44:3305-3308.
40. 2O-HCl. Indian J. Chem. 2008, 47B:434-438.
41. Quan Z.J., Da Y.X., Zhang Z., Wang X.C. PS-PEG-SO3H as an efficient catalyst for 3,4-dihydropyrimidones via Biginelli reaction. Catal. Commun. 2009, 10:1146-1148.
42. Rafiee E., Shahbazi F. One-pot synthesis of dihydropyrimidones using silica-supported heteropoly acid as an efficient and reusable catalyst: Improved protocol conditions for the Biginelli reaction. J. Mol. Catal. A: Chem. 2006, 250:57.
43. Ramalingan C., Park S.J., Lee I.S., Kwak Y.W. A piperidinium triflate catalyzed Biginelli reaction. Tetrahedron 2010, 66:2987-2994.
44. Ramu E., Kotra V., Bansal N., Varala R., Adapa S.R. Green approach for the efficient synthesis of Biginelli compounds promoted by citric acid under solvent-free conditions. Rasayan J. Chem. 2008, 1:188-194.
45. Rives V., Ulibarri M.A. Layered double hydroxides (LDH) intercalated with metal coordination compounds and oxometalates. Coord. Chem. Rev. 1999, 181:61-120.
46. 2 under neat conditions: optimized green alternatives for the Biginelli reaction. Tetrahedron Lett. 2007, 48:5777-5780.
47. Saini A., Kumar S., Sandhu J.S. Gallium(III) halides catalyzed, microwave enhanced, synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free condition. Indian J. Chem. 2007, 46B:1886-1889.
48. Sangshetti J.N., Kokare N.D., Shinde D.B. Oxalic acid as a versatile catalyst for one pot facile synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their thione analogues. J. Heterocycl. Chem. 2008, 45:1191-1194.
49. Shaabani A., Rahmati A. Ionic liquid promoted efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. Catal. Lett. 2005, 100:177-179.
50. 3H as efficient catalysts for modified preparation of 3,4-dihydropyrimidin-2(1H)-ones/thiones. Phosphorus, Sulfur, Silicon Relat. Elem. 2009, 184:2333-2338.
51. Singh K., Arora D., Singh S. Genesis of dihydropyrimidinone calcium channel blockers: recent progress in structure-activity relationships and other effects. Mini-Rev. Med. Chem. 2009, 9:95-106.
52. Venkateshwar Reddy Ch., Mahesh M., Raju P.V.K., Ramesh Babu T., Narayana Reddy V.V. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2002, 43:2657-2659.
53. 3: A highly active and reusable heterogeneous catalyst for the one-pot synthesis of dihydropyrimidinones. J. Heterocycl. Chem. 2008, 45:1771-1774.
54. 3H as an efficient catalyst for 3,4-dihydropyrimidones. Catal. Commun. 2009, 10:1146.
55. Wipf P., Cunningham A. A solid phase protocol of the Biginelli dihydropyrimidine synthesis suitable for combinatorial chemistry. Tetrahedron Lett. 1995, 36:7819-7822.
56. Yu Y., Liu D., Liu C., Jiang H., Luo G. An efficient one-pot Biginelli condensation of aliphatic aldehydes catalyzed by zinc bromide under solvent-free conditions. Prep. Biochem. Biotechnol. 2007, 37:381-387.
57. Zhang Z., Zhou S., Nie J. Polymer-supported sulfonimide as a novel water-tolerant Brønsted acid catalyst for esterification of equimolar carboxylic acids and alcohols. J. Mol. Catal. A: Chem. 2007, 265:9-14.
58. Zumpe F.L., Flu M., Schmitz K., Lender A. Propane phosphonic acid anhydride: a new promoter for the one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Lett. 2007, 48:1421-1423.