Convenient oxidation of alkylated phenols and methoxytoluenes to antifungal 1,4-benzoquinones with hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3) catalytic system in neutral ionic liquid

Tetrahedron

Volumn 62, Issue 33, 2006, Pages 7733-7737

  Bernini, Roberta ^a,b   Mincione, Enrico ^a,b   Barontini, Maurizio ^a,b   Fabrizi, Giancarlo ^c   Pasqualetti, Marcella ^a   Tempesta, Sabrina ^a  

^a UNIVERSITY OF TUSCIA   (Italy)

^b Unita di Ricerca VT2   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

1,4 Benzoquinones; 1 Butyl 3 methylimidazolium tetrafluoroborate bmim BF4; Antifungal activity; Catalytic oxidations; Hydrogen peroxide methyltrioxorhenium

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM TETRAFLUOROBORATE; 1,4 BENZOQUINONE; 2 METHOXY 5 METHYL 1,4 BENZOQUINONE; 2 TERT BUTYL 5 METHYL 1,4 BENZOQUINONE; 2 TERT BUTYL 6 METHYL 1,4 BENZOQUINONE; 2,3,5 TRIMETHYLBENZOQUINONE; 2,6 DI TERT BUTYL 1,4 BENZOQUINONE; 2,6 DIISOPROPYL 1,4 BENZOQUINONE; ANTIFUNGAL AGENT; BENZOQUINONE; DIMETHOXY 5 METHYL 1,4 BENZOQUINONE; HYDROGEN PEROXIDE; IONIC LIQUID; KETOCONAZOLE; METHOXYTOLUENE; METHYLTRIOXORHENIUM; PHENOL; RHENIUM; TOLUENE; UNCLASSIFIED DRUG;

ALKYLATION; ANTIFUNGAL ACTIVITY; ARTICLE; CATALYSIS; FUNGUS GROWTH; FUSARIUM; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SOIL;

FUNGI; FUSARIUM SP.;

EID: 33745584055     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.069     Document Type: Article

References (55)

1. Lipshutz B.H., Mollard P., Pfeiffer S.S., and Chrisman W. J. Am. Chem. Soc. 124 (2002) 14282-14283 and references therein
2. Rodriguez J., Quinoa E., Riguera R., Peters B.M., Abrell L.M., and Crews P. Tetrahedron 48 (1992) 6667-6680
3. Letcher R.M., and Wong M.C. J. Chem. Soc., Perkin Trans. 1 (1992) 3035-3037
4. Hakura A., Mochida H., Tsutsur Y., and Yamatsu K. Mutat. Res. 347 (1994) 37-43
5. Lund A.K., Adsernen A., and Nyman U. Phytomedicine 5 (1998) 199-203
6. Gonzalez-Ibarra M., Farfan N., Trejo C., Uribe S., and Lotina-Hennsen B. J. Agric. Food Chem. 53 (2005) 3415-3420
7. Nishina A., and Uchibori T. Agric. Biol. Chem. 55 (1991) 2395-2398
8. Meazza G., Dayan F.E., and Wedge D.E. J. Agric. Food Chem. 51 (2003) 3824-3828
9. Schudel P., Mayer H., and Isler O. In: Sebrell W.H., and Harris R.S. (Eds). The Vitamins Vol. 5 (1972), Academic, New York, NY 165
10. Yamada S., Takeshita T., and Tanaka J. J. Synth. Org. Chem. Jpn. 40 (1982) 268-270
11. Quideau S., and Pouysegu L. Org. Prep. Proced. Int. 31 (1999) 617-668 and references therein
12. Brimble M.A., Duncalf L.J., and Phytion S.J. J. Chem. Soc., Perkin Trans. 1 (1997) 1399-1401
13. McKillop A., Perry D.H., Edwards M., Antus S., Farkas L., Nogrady M., and Taylor E.C. J. Org. Chem. 41 (1976) 282-287 and references therein
14. Kato N., Sugaya T., Mimura T., Ikuta M., Kato S., Kuge Y., Tomioka S., and Kasai M. Synthesis (1997) 625-627
15. Tohma H., Morioka H., Harayama Y., Hashizume M., and Kita T. Tetrahedron Lett. 42 (2001) 6899-6901
16. Land T. In: Stoddart J.F. (Ed). Comprehensive Organic Chemistry Vol. 1 (1979), Pergamon, Oxford 1216
17. Itoh S., Ogino M., Haranou S., Terasaka T., Ando T., Komatsu M., Ohshiro Y., Fukuzumi S., Kano K., Takagi K., and Ideka T. J. Am. Chem. Soc. 117 (1995) 1485-1493
18. Cherkaoui O., Nebois P., Fillion H., Domard M., and Fenet B. Tetrahedron 52 (1996) 9499-9508
19. Liotta D., Arbiser J., Short J.W., and Saindane M. J. Org. Chem. 48 (1983) 2932-2933
20. Pratt D.V., Ruan F., and Hopkins P.B. J. Org. Chem. 52 (1987) 5053-5055
21. Mostaghim R., and Ahmadibeni Y. Acta Chim. Slov. 50 (2003) 569-572
22. Kholdeeva, O. A.; Trukhan, N. N.; Parmon, V. N.; Yarzhebskii, A.; Mrovets Belon, U., RU 2196764, 2003.
23. Dewkar G.K., Shaikh T.M., Pardhy S., Kulkarni S.S., and Sudalai A. Indian J. Chem., Sect. B 44B (2005) 1530-1532
24. Dewkar, G. K.; Thakur, V. V.; Pardhy, S. A.; Sudalai, A.; Devolta, S. U.S. Patent 6,872,857, 2005.
25. Mohapatra S.K., Hussain F., and Selvam P. Catal. Commun. (2003) 57-62
26. Isawa S., Fakhruddin A., Widagdo H.S., and Nishiyama H. Adv. Synth. Catal. 347 (2005) 517-520
27. Owsik I., and Kolarz B. J. Mol. Catal. A: Chem. 178 (2002) 63-71
28. Kholdeeva O.A., Trukhan N.N., Vanina M.P., Romannikov V.N., Parmon V.N., Mrrwiec-Bialon J., and Jarzebski A.B. Catal. Today 75 (2002) 204-210
29. Adam W., Herrmann W.A., Lin J., and Saha-Moller C.R. J. Org. Chem. 59 (1994) 8281-8283
30. Adam W., Herrmann W.A., and Saha-Moller C.R. J. Mol. Catal. A: Chem. 97 (1995) 15-20
31. Saladino R., Neri V., Mincione E., and Filippone P. Tetrahedron 58 (2002) 8493-8500
32. Bernini R., Coratti A., Fabrizi G., and Goggiamani A. Tetrahedron Lett. 44 (2003) 8991-8994
33. Bernini R., Coratti A., Fabrizi G., and Goggiamani A. Tetrahedron Lett. 46 (2005) 6169-6170
34. Bernini R., Mincione E., Coratti A., Fabrizi G., and Battistuzzi G. Tetrahedron 60 (2004) 967-971
35. Bernini R., Coratti A., Provenzano G., Fabrizi G., and Tofani D. Tetrahedron 61 (2005) 1821-1825
36. Earle M., Forestier A., Olivier-Bourbigou H., and Wasserscheid P. In: Wasserscheid P., and Welton T. (Eds). Ionic Liquids in Synthesis (2003), Wiley-VCH, Weinheim 174-257 Chapter 5
37. Seddon K.R. J. Chem. Technol. Biotechnol. 68 (1997) 351-356
38. Sheldon R. Chem. Commun. (2001) 2399-2407
39. Sun H., Harms K., and Sundermeyer J. J. Am. Chem. Soc. 126 (2004) 9550-9551
40. Sun H., Li X., and Sundermeyer J. J. Mol. Catal. A: Chem. 240 (2005) 119-122
41. Niculescu-Duvaz I., Safarman C., Stoica G., Lupu F., Amannu M., and Voiculetz N. Oncologia 2 (1987) 109-113
42. Niculescu-Duvaz I., Safarman C., Stoica G., Lupu F., Amannu M., and Voiculetz N. Neoplasma 39 (1988) 539-548
43. Niculescu-Duvaz I., Herdan J., Stoica G., Lupu F., Arnautu M., Cinca S., Eliescu R., and Voiculetz N. Neoplasma 38 (1991) 545-548
44. Colovai A., Herdan J., Popovic C., Mihai C., Grigoras C., Voiculetz N., and Nicolescu-Duvaz I. Carcinogenesis 14 (1993) 1137-1141
45. McGinnis M.R., and Rinaldi M.G. In: Lorian V. (Ed). Antibiotics in Laboratory Medicine. 4th ed. (1996), Williams and Wilkins, Baltimore, MD 176-211
46. Holbrey J.D., and Seddon K.R. J. Chem. Soc., Dalton Trans. (1999) 2133-2136
47. Omura K. J. Org. Chem. 54 (1989) 1987-1990
48. Omura K. Synthesis (1998) 1145-1148
49. Weyler J.W., Duncan W.G., and Moore H.W. J. Am. Chem. Soc. 97 (1975) 6187-6192
50. McKillop A., Swann B.P., and Taylor E.C. Tetrahedron 26 (1970) 4031-4039
51. Pelter A., and Elgendy S. Tetrahedron Lett. 29 (1988) 677-680
52. Villemin D., Hammadi M., and Hachemi M. Synth. Commun. 32 (2002) 1501-1515
53. Takizawa Y., Iwasa Y., Suzuki T., and Miyaji H. Chem. Lett. (1993) 1863-1865
54. Keinan E., and Eren D. J. Org. Chem. 52 (1987) 3872-3875
55. Ryu C.-K., Kang H.-Y., Yi Y.-J., Shin K.-H., and Lee B.-H. Bioorg. Med. Chem. Lett. 10 (2000) 1589-1591