Microwave assisted syntheses of 2,5-disubstituted 1,3,4-oxadiazoles

Tetrahedron Letters

Volumn 45, Issue 47, 2004, Pages 8753-8756

  Rostamizadeh, Shahnaz ^a   Housaini, S A Ghasem ^a  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

1,3,4 Oxadiazoles; Microwave irradiation; Oxidation; Solid support

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; ACETONE; PERMANGANATE POTASSIUM; WATER;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; OXIDATION; SOLID;

EID: 7044245919     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.09.095     Document Type: Article

References (51)

1. F. Toda, M. Yagi, and K.J. Kiyoshigo J. Chem. Soc., Chem. Commun. 1988 958
2. G.R. Dessiraju Organic Solid State Chemistry 1987 Elsevier Amsterdam
3. M. Balogh, and P. Laszlo Organic Chemistry Using Clays 1992 Springer Berlin
4. K. Smith Solid Supports and Catalysts in Organic Synthesis 1992 Ellis Harwood, PTR, Prentice Hall New York
5. R.S. Varma Green Chem. 1999 43
6. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Francoise, and D. Mathe Synthesis 1998 1213
7. E. Palaska, G. Sahin, P. Kelicen, N. Tugbadurlu, and G. Altinok IL Farmaco 57 2002 101
8. H. Dogan, A. Daran, S. Rollas, G. Sener, M.K. Uysal, and D. Gulen Bioorg. Med. Chem. 10 2002 2893
9. G.W. Adelstein, Ch.H. Yen, E.Z. Dajani, and R.G. Bianchi J. Med. Chem. 19 1976 1221
10. Angelini, I.; Angelini, L.; Sparaco, F. Brit. Pat. 1.161.801, 1966/1969; Chem. Abstr. 1969, 71, 112937
11. P. Brown, D.J. Best, N.J.P. Broom, R. Cassels, P.J. Bhanlon, T.J. Mitchell, N.F. Osborne, and J.M. Wilson J. Med. Chem. 40 1997 2563
12. H. Singh, L.D.S. Yadava, and J.P. Chaudharg Acta Chem. Hung. 118 1985 11
13. H.L. Yale, and K. Losee J. Med. Chem. 9 1966 478
14. V.N. Kerr, D.G. Ott, and F.N. Hayes J. Am. Chem. Soc. 812 1960 186
15. M. Al-Talib, H. Tastoush, and N. Odeh Synth. Commun. 20 1990 1811
16. P.H.J. Carlsen, and K.B. Jorgensen J. Heterocycl. Chem. 31 1994 805
17. E. Klinsberg J. Am. Chem. Soc. 80 1958 5786
18. A.B. Theocharis, and N.E. Alexandrou J. Heterocycl. Chem. 27 1990 1685
19. S. Liras, M.P. Allen, and B.E. Segelstein Synth. Commun. 30 2000 437
20. W.R. Tully, C.R. Gardner, R.J. Gillespie, and R. Westwood J. Med. Chem. 34 1991 2060
21. F.W. Short, and L.N. Long J. Heterocycl. Chem. 6 1969 707
22. T.F. Osipova, G.I. Koldobskii, and V.A. Ostrovskii Zh. Org. Khim. 20 1984 1119
23. Chem. Abstr. 101 1984 110832j
24. K.S. Balachandran, and M.V. George Tetrahedron 29 1973 2119
25. T. Chiba, and M. Okimoto J. Org. Chem. 57 1992 1375
26. R. Yang, and L. Dai J. Org. Chem. 58 1993 3381
27. P.S.N. Reddy, and P.R. Reddy Indian J. Chem. 26B 1987 890
28. V.K. Tandon, and R.B. Chhor Synth. Commun. 31 2001 1727
29. S.H. Mashraqui, Sh.G. Ghadigaonkar, and R.S. Kenny Synth. Commun. 33 2003 2541
30. F. Bentiss, M. Lagrenee, and D. Barbry Synth. Commun. 31 2001 935
31. B.J. Brown, I.R. Clemens, and J.K. Neesom Synlett 2000 131
32. C.T. Brain, and Sh.A. Brunton Synlett 2001 382
33. C.T. Brain, J.M. Paul, Y. Loong, and P.J. Oakley Tetrahedron Lett. 40 1999 3275
34. P. Wipf, and S. Venkatraman Tetrahedron Lett. 37 1996 4659
35. Microwave irradiation was carried out using a commercial Moulinex AET 5 microwave oven
36. 4 and evaporated in vacuo. The precipitated solids were crystallized from ethanol
37. (b) General procedure for the synthesis of 1-aroyl-2-arylidene hydrazines in ethanol: a mixture of the acid hydrazide (6 mmol) and aldehyde (6 mmol) was dissolved in ethanol (25 mL). Then, three drops of phosphoric acid was added and the mixture placed in a Teflon vessel. The mixture was then subjected to microwave irradiation at 150 W. After complete conversion as indicated by TLC, the reaction mixture was cooled and the precipitated solids were filtered off. All the products were then recrystallized from ethanol
38. All the 1,3,4-oxadiazoles prepared are known compounds and were characterized by comparison of their spectral and physical data with those of known samples
39. (a) General procedure for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles (on the surface of silica gel): a mixture of 1-aroyl-2-arylidene hydrazines (3 mmol), potassium permanganate (15 mmol), and silica gel (10 g) was thoroughly ground in a mortar. The mixture was then subjected to microwave irradiation in an open Pyrex beaker for the appropriate time at 350 W (Table 2). After complete conversion as indicated by TLC, the mixture was extracted with chloroform and the products were identified by comparison with known samples. The same procedure was used in the case of other solid supports
40. 4. The solvent was evaporated in vacuo and the precipitated solids were recrystallized directly from an appropriate solvent
41. D.G.I. Kingston, and H.P. Tannenbaum J. Chem. Soc. (C) 1970 2574
42. S. Lirase, and P.A. Martin J. Am. Chem. Soc. 49 1927 286
43. J.S. Agarwal Chem. Ber. 35 1929 1941
44. M. Uher, and J. Foltin Coll. Czech. Chem. Commun. 46 1981 1492
45. R. Milcent J. Heterocycl. Chem. 20 1983 77
46. A.P. Grekov, and L.N. Kulakova Zh. Obshch. Khim. 29 1959 3054
47. Chem. Abstr. 54 1960 13108g
48. A.P. Grekov, and O.P. Shvaika Stsintllyatoryist Koordinates 105 1957 14
49. Chem. Abstr. 58 1963 5663a
50. R. Huisgen, J. Sauer, and J.H. Markgraf Chem. Ber. 93 1960 2106
51. F.N. Hayes, B.S. Rogers, and D.G. Ott J. Am. Chem. Soc. 77 1955 1850