Silica-bonded S-sulfonic acid: an efficient and recyclable solid acid catalyst for the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols)

Tetrahedron Letters

Volumn 51, Issue 4, 2010, Pages 692-694

  Niknam, Khodabakhsh ^a   Saberi, Dariush ^a   Sadegheyan, Mohsen ^a   Deris, Abdollah ^a  

^a PERSIAN GULF UNIVERSITY   (Iran)

Author keywords

4,4 (Arylmethylene)bis(1H 5 pyrazol 5 ols); 5 Methyl 2 phenyl 2,4 dihydro 3H pyrazol 3 one; Aldehydes; Silica bonded S sulfonic acid

Indexed keywords

ALDEHYDE DERIVATIVE; PYRAZOLONE DERIVATIVE; SILICON DIOXIDE; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; POLYMERIZATION;

EID: 72149102674     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.114     Document Type: Article

References (32)

1. McDonald E., Jones K., Brough P.A., Drysdale M.J., and Workman P. Curr. Top. Med. Chem. 6 (2006) 1193-1203
2. Elguero J. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 5. (1996), Oxford, Pergamon
3. Elguero J., Goya P., Jagerovic N., and Silva A.M.S. Targets Heterocycl. Syst. 6 (2002) 52-98
4. Sugiura S., Ohno S., Ohtani O., Izumi K., Kitamikado T., Asai H., and Kato K. J. Med. Chem. 20 (1977) 80-85
5. Behr L.C., Fusco R., and Jarboe C.H. In: Weissberger A. (Ed). The Chemistry of Heterocyclic Compounds, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings (1967), Interscience, New York
6. Rosiere C.E., and Grossman M.I. Science 113 (1951) 651
7. Bailey D.M., Hansen P.E., Hlavac A.G., Baizman E.R., Pearl J., Defelice A.F., and Feigenson M.E. J. Med. Chem. 28 (1985) 256-260
8. Mahajan R.N., Havaldar F.H., and Fernandes P.S. J. Indian Chem. Soc. 68 (1991) 245-246
9. Chauhan P.M.S., Singh S., and Chatterjee R.K. Indian J. Chem., Sect. B 32 (1993) 858-861
10. Singh D., and Singh D. J. Indian Chem. Soc. 68 (1991) 165-167
11. Londershausen M. Pestic. Sci. 48 (1996) 269-292
12. In: Lubs H.A. (Ed). The Chemistry of Synthetic Dyes and Pigments (1970), American Chemical Society, Washington, DC
13. Uzoukwu A.B. Polyhedron 12 (1993) 2719-2724
14. Maurya R.C., and Verma R. Indian J. Chem., Sect. A 36 (1997) 596-598
15. Garnovskii A.D., Uraev A.I., and Minkin V.I. Arkivoc iii (2004) 29-41
16. Sridhar R., Perumal P.T., Etti S., Shanmugam G., Ponnusamy M.N., Prabavathy V.R., and Mathivanan N. Bioorg. Med. Chem. Lett. 14 (2004) 6035-6040
17. Sivaprasad G., Perumal P.T., Prabavathy V.R., and Mathivanan N. Bioorg. Med. Chem. Lett. 16 (2006) 6302-6305
18. Hamama W.S. Synth. Commun. 31 (2001) 1335-1345
19. Li X.-L., Wang Y.-M., Tian B., Matsuura T., and Meng J.-B. J. Heterocycl. Chem. 35 (1998) 129-134
20. Singh D., and Singh D. J. Chem. Eng. Data 29 (1984) 355-356
21. Mitra A.S., and Rout M.K. J. Indian Chem. Soc. 38 (1961) 893
22. Pavlov P.T., Goleneva A.F., Lesnov A.E., and Prokhorova T.S. Pharm. Chem. J. (Engl. Trans.) 32 (1998) 370-372
23. Buzykin B.I., and Lonshchakova T.I. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Trans.) (1971) 2224-2226
24. Wang W., Wang S.-X., Qin X.-Y., and Li J.-T. Synth. Commun. 35 (2005) 1263-1269
25. Elinson M.N., Dorofeev A.S., Nasybullin R.F., and Nikishin G.I. Synthesis 12 (2008) 1933-1937
26. Sujatha K., Shanthi G., Selvam N.P., Manoharan S., Perumal P.T., and Rajendran M. Bioorg. Med. Chem. Lett. 19 (2009) 4501-4503
27. Niknam K., Saberi D., and Nouri Sefat M. Tetrahedron Lett. 50 (2009) 4058-4062
28. Niknam K., Saberi D., and Mohagheghnejad M. Molecules 14 (2009) 1915-1926
29. Niknam K., Saberi D., and Baghernejad M. Chin. Chem. Lett. 20 (2009) 1444-1448
30. Niknam K., and Saberi D. Tetrahedron Lett. 50 (2009) 5210-5214
31. Niknam K., and Saberi D. Appl. Catal. A: Gen. 366 (2009) 220-225
32. 27,28 the loading of 3-mercaptopropylsilica 1 is 0.33 mmol/g.General procedure: A mixture of aromatic aldehyde (1 mmol), 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (2 mmol) and SBSSA (0.1 g) in ethanol (10 mL) were added to a flask and heated under refluxing conditions for an appropriate time. After the completion of the reaction, as indicated by TLC, the reaction mixture was washed with warm ethanol (3 × 30 mL). After cooling, the crude products were precipitated. The crude products were purified by recrystallization from ethanol (95%). The recovered catalyst was washed with diethyl ether, dried, and reused for subsequent runs.