Silica sulfuric acid: An efficient and versatile acidic catalyst for the rapid and ecofriendly synthesis of 1,3,4-oxadiazoles at ambient temperature

Synthetic Communications

Volumn 37, Issue 7, 2007, Pages 1201-1209

  Dabiri, Minoo ^a   Salehi, Peyman ^a   Baghbanzadeh, Mostafa ^a   Zolfigol, Mohammad Ali ^b   Bahramnejad, Mahboobeh ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

^b BU ALI SINA UNIVERSITY   (Iran)

Author keywords

1,3,4 oxadiazoles; Heterocycles; Heterogeneous catalysis; Silica sulfuric acid; Solvent free

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; ESTER DERIVATIVE; HYDRAZIDE DERIVATIVE; SILICON DIOXIDE; SOLVENT; SULFURIC ACID;

ARTICLE; CATALYST; CHEMICAL REACTION; ENVIRONMENTAL TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34147094087     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701199151     Document Type: Article

References (46)

1. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
2. Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Discovery Today 2003, 8, 1128-1137.
3. Shi, W.; Qian, X.; Zhang, R.; Song, G. Synthesis and quantitative structure-activity relationships of new 2,5-disubstituted-1,3,4-oxadiazoles. J. Agric. Food Chem. 2001, 49, 124-130.
4. Meng, H.; Hung, W. Novel photoluminescent polymers containing oligothiophene and m-phenylene-1,3,4-oxadiazole moieties: Synthesis and spectroscopic and electrochemical studies. J. Org. Chem. 2000, 65, 3894-3901.
5. Meng, H.; Chen, Z.; Liu, X.; Lia, Y.; Chua, S.; Huang, W. Synthesis and characterization of a novel blue electroluminescent polymer constituted of alternating carbazole and aromatic oxadiazole units. Phys. Chem. Chem. Phys. 1999, 1, 3123-3127.
6. Bottino, F. A.; Pasquale, G. D.; Innelli, P. Synthesis, characterization, and study of the thermal properties of new poly(arylene ether 1,3,4-oxadiazoles). Macromolecules 2001, 34, 33-37.
7. Tamoto, N.; Adachi, C.; Nagai, K. Electroluminescence of 1,3,4-oxadiazole and triphenylamine-containing molecules as an emitter in organic multilayer light emitting diodes. Chem. Mater. 1997, 9, 1077-1085.
8. Perez, M. A.; Bermejo, J. M. Synthesis of multidentate 1,3,4-oxadiazole containing, imine-containing, and phenol-containing macrocycles. J. Org. Chem. 1993, 58, 2628-2630.
9. Lee, D. W.; Kwon, K.-Y.; Jin, J. I.; Park, Y.; Kim, Y.-R.; Hwang, I.-W. Luminescence properties of structurally modified PPVs: PPV derivatives bearing 2-(4-tert-butylphenyl)-5-phenyl-1,3,4-oxadiazole pendants. Chem. Mater. 2001, 13, 565-574.
10. Orlek, B. S.; Blaney, F. E.; Brown, F.; Clark, M. S. G.; Hadley, M. S.; Hatcher, J.; Riley, G. J.; Rosenberg, H. E.; Wadsworth, H. J.; Wyman, P. Comparison of azabycyclic esters and oxadiazoles as ligands for the muscarinic receptor. J. Med. Chem. 1991, 34, 2726-2735.
11. Watjen, F.; Baker, R.; Engelstoff, M.; Herbert, R.; MacLeod, A.; Knight, A.; Merchant, K.; Moseley, J.; Saunders, J.; Swain, C. J.; Wong, E.; Springer, J. P. Novel benzodiazepine receptor partial agonists - Oxadiazolylimidazobenzodiazepines. J. Med. Chem. 1989, 32, 2282-2291.
12. Carroll, F. I.; Gray, J. L.; Abrahm, P.; Kuzemko, M. A.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. 3-Aryl-2-(3′-substituted-1′,2′, 4′-oxadiazol-5′-yl)tropain analogs of cocaine - Affinities at the cocaine binding-site at the dopamine, serotonin, and norepinephrine transporters. J. Med. Chem. 1993, 36, 2886-2890.
13. Diana, G. D.; Volkots, D. L.; Nitz, T. J.; Bailey, T. R.; Long, M. A.; Vescio, N.; Aldous, S.; Pevear, D. C.; Dutko, F. J. Oxadiazoles as ester bioisosteric replacementes in compounds related to disoxaril - antirhinovirus activity. J. Med. Chem. 1994, 37, 2421-2436.
14. Ankersen, M.; Peschke, B.; Hansen, B. S.; Hansen, T. K. Investigation of bioisosters of the growth hormone secretagogue L-692,429. Bioorg. Med. Chem. Lett. 1997, 7, 1293-1298.
15. Chen, H.; Li, Z.; Han, Y. J. Agric. Food Chem. 2000, 48, 5312-5315.
16. Deshmukh, A. A.; Sattur, P. B.; Sheth, U. K. Synthesis and pharmacology of 2,3-diphenylpropionhydrazides and hydrazones. Indian. J. Exp. Biol. 1976, 14, 166-168.
17. Sen Gupta, A. K.; Garg, M.; Chandra, U. Synthesis and biological activity of some new N-3(2phenyl quinazolin (3H)-4-one) acyl hydrazones. J. Indian Chem. Soc. 1979, 56, 645-647.
18. Zheng, X.; Li, Z.; Wang, Y.; Chen, W.; Huang, Q.; Liu, C.; Song, G. J. Flourine Chem. 2003, 123, 163-169.
19. Khan, M. T. H.; Choidhary, M. I.; Khan, K. M.; Rani, M.; Rahman, A. Structure-activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues. Bioorg. Med. Chem. 2005, 13, 3385-3395.
20. Zarghi, A.; Tabatabai, S. A.; Faizi, M.; Ahadian, A.; Navabi, P.; Zanganeh, V.; Shafiee, A. Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles. Bioorg. Med. Chem. Lett. 2005, 15, 1863-1865.
21. Hayes, F. N.; Rogers, B. S.; Ott, D. J. 2,5-Diaryloxazoles and 2,5-diaryl-1,3,4-oxadiazoles. J. Am. Chem. Soc. 1955, 77, 1850-1852.
22. El Kaim, L.; Le Menestrel, I.; Morgentin, R. Trichloroacetic acid hydrazones I: New formation of 1,3,4-oxadiazoles from aldehydes. Tetrahedron Lett. 1998, 39, 6885-6888.
23. Khan, K. M.; Ullah, Z.; Rani, M.; Perveen, S.; Haider, S. M.; Choudhary, M. I.; Rahman, A.; Voelter, W. Microwave-assisted synthesis of 2,5-disubstituted-1,3,4-oxadiazoles. Lett. Org. Chem. 2004, 1, 50-52.
24. Loffler, J.; Schobert, R. Synthesis of 1,3,4-oxadiazoles from carboxylic hydrazides and of 1,2-oxazin-6-ones from alpha-(hydroxyimino)carboxylic esters with keteneylidene triphenylphosphorane. Synlett 1997, 283-284.
25. Herrero, M. A.; Wannberg, J.; Larhed, M. Direct microwave synthesis of N,N′-diacylhydrazines and boc-protected hydrazides by in situ carbonylations under air. Synlett 2004, 2335-2338.
26. Kosmrlj, J.; Kocevar, M.; Polanc, S. A mild approach to 1,3,4-oxadiazoles and fused 1,2,4-triazoles. Diazenes as intermediates? Synlett 1996, 652-654.
27. Rostamizadeh, S.; Housaini, G. Microwave-assisted syntheses of 2,5-disubstituted 1,3,4-oxadiazoles. Tetrahedron Lett. 2004, 45, 8753-8756.
28. Rao, V. S.; Sekhar, V. G. C. Iodobenzene diacetate mediated solid-state synthesis of heterocyclyl-1,3,4-oxadiazoles. Synth. Commun. 2004, 34, 2153-2157.
29. Ainsworth, C. The condensation of aryl carboxylic acid hydrazides with orthoesters. J. Am. Chem. Soc. 1955, 77, 1148-1150.
30. Leiby, R. W. J. Heterocycl. Chem. 1984, 21, 1825-1832.
31. Shafiee, A.; Naimi, E.; Mansobi, P.; Foroumadi, A.; Shekari, M. Syntheses of substituted -oxazole-1,3,4-thiadiazoles, 1,3,4-oxadiazoles, and 1,2,4-triazoles. J. Heterocycl. Chem. 1995, 32, 1235-1239.
32. Khajavi, M. S.; Sadat Hosseini, S. S.; Sefidkon, F. Iran. J. Chem. Chem. Eng. 1997, 16, 68-71.
33. Brown, B. J.; Clemens, I. R.; Neesom, J. K. Diisopropylcarbodiimide: A novel reagent for the synthesis of 1,3,4-oxadiazoles on solid-phase. Synlett 2000, 131-133.
34. Hebert, N.; Hannah, A. L.; Sutton, S. C. Synthesis of oxadiazoles on solid support. Tetrahedron Lett. 1999, 40, 8547-8550.
35. Brain, C. T.; Paul, J. M.; Loong, Y.; Okaley, P. J. Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions. Tetrahedron Lett. 1999, 40, 3275-3278.
36. Kilburn, J. P.; Lau, J.; Jones, R. C. F. 1,3,4-Oxadiazole formation: A novel solid support strategy. Tetrahedron Lett. 2001, 42, 2583-2586.
37. Coppo, F. T.; Evans, K. A.; Graybill, T. L.; Burton, G. Efficient one-pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents. Tetrahedron Lett. 2004, 45, 3257-3260.
38. Sugiono, E.; Detert, H. Functionalisation of 2-(1-naphthyl)-5-phenyl-1,3, 4-oxadiazol with alkoxysilanes. Synthesis 2001, 893-896.
39. Park, Y.-D.; Kim, J.-J.; Chung, H.-A.; Keweon, D.-H.; Cho, S.-D.; Lee, S. G.; Yoon, Y.-J. Facile synthesis of symmetric and unsymmetric 1,3,4-oxadiazoles using 2-acyl(or aroyl)pyridazin-3-ones. Synthesis 2003, 560-564.
40. Young, J. R.; DeVita, R. J. Novel synthesis of oxadiazoles via palladium catalysis. Tetrahedron Lett. 1998, 39, 3931-3934.
41. Dabiri, M.; Salehi, P.; Mohammadi, A. A.; Baghbanzadeh, M. One-pot synthesis of mono- and disubstituted (3H)-quinazolin-4-ones in dry media under microwave irradiation. Synth. Commun. 2005, 35, 279-287.
42. Salehi, P.; Dabiri, M.; Khosropour, A. R.; Roozbehniya, P. Diammonium hydrogen phosphate: A versatile and inexpensive reagent for one-pot synthesis of dihydropyrimidinones, quinazolinones and azalactones under solvent-free conditions. J. Iran. Chem. Soc. 2006, 3, 98-104.
43. Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025-1047, and other references cited therein.
44. 2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions. Tetrahedron 2001, 57, 9509-9511.
45. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Baghbanzadeh, M. A novel method for the one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)- ones. Synlett 2005, 1155-1157.
46. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Baghbanzadeh, M. A new approach to the facile synthesis of mono- and disubstituted quinazolin-4(3H)-ones under solvent-free conditions. Tetrahedron Lett. 2005, 46, 7051-7053.