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

被引:44
作者
Bernini, Roberta
Mincione, Enrico
Barontini, Maurizio
Fabrizi, Giancarlo
Pasqualetti, Marcella
Tempesta, Sabrina
机构
[1] Univ Tuscia, Dipartimento Agrobiol & Agrochim, I-01100 Viterbo, Italy
[2] Consorzio Interuniv La Chim Ambiente, Unita Ric VT2, I-30175 Marghera, VE, Italy
[3] Univ Roma La Sapienza, Dipartimento Studi CHim & Tecnol Sostanze Biologi, I-00185 Rome, Italy
[4] Univ Tuscia, Dipartimento Ecol & Sviluppo Econ Sostenibile, I-01100 Viterbo, Italy
关键词
hydrogen peroxide/methyltrioxorhenium; catalytic oxidations; 1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4; 1,4-benzoquinones; antifungal activity;
D O I
10.1016/j.tet.2006.05.069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkylated phenol and methoxytoluene derivatives were catalytically and selectively oxidized to the corresponding 1,4-benzoquinones in good conversions and yields. Reactions were performed with hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3) in 1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4, aneutral ionic liquid. Compounds were tested in vitro for their antifungal activity against the growth of several widespread soil fungi. Some of them were proved to be potent inhibitors of Fusarium sp. than ketoconazole, a commercially available and expensive antifungal agent. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7733 / 7737
页数:5
相关论文
共 56 条
[11]  
Dewkar GK, 2005, INDIAN J CHEM B, V44, P1530
[12]  
DEWKAR GK, 2005, Patent No. 6872857
[13]   Selective herbicide activity of 2,5-di(benzylamine)-p-benzoquinone against the monocot weed Echinochloa crusgalli.: An in vivo analysis of photosynthesis and growth [J].
González-Ibarra, M ;
Farfán, N ;
Trejo, C ;
Uribe, S ;
Lotina-Hennsen, B .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (09) :3415-3420
[14]   MUTAGENICITY OF BENZOQUINONES FOR AMES SALMONELLA TESTER STRAINS [J].
HAKURA, A ;
MOCHIDA, H ;
TSUTSUI, Y ;
YAMATSU, K .
MUTATION RESEARCH LETTERS, 1995, 347 (01) :37-43
[15]   The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals [J].
Holbrey, JD ;
Seddon, KR .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (13) :2133-2139
[16]   A MODEL-COMPOUND OF NOVEL COFACTOR TRYPTOPHAN TRYPTOPHYLQUINONE OF BACTERIAL METHYLAMINE DEHYDROGENASES - SYNTHESIS AND PHYSICOCHEMICAL PROPERTIES [J].
ITOH, S ;
OGINO, M ;
HARANOU, S ;
TERASAKA, T ;
ANDO, T ;
KOMATSU, M ;
OHSHIRO, Y ;
FUKUZUMI, S ;
KANO, K ;
TAKAGI, K ;
IKEDA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (05) :1485-1493
[17]   A rapid and efficient synthesis of quinone derivatives: Ru(II)- or Ir(I)-catalyzed hydrogen peroxide oxidation of phenols and methoxyarenes [J].
Iwasa, S ;
Fakhruddin, A ;
Widagdo, HS ;
Nishiyama, H .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :517-520
[18]  
Kato N, 1997, SYNTHESIS-STUTTGART, P625
[19]   TOTAL SYNTHESIS OF LINEAR POLYPRENOIDS .2. IMPROVED PREPARATION OF THE AROMATIC NUCLEUS OF UBIQUINONE [J].
KEINAN, E ;
EREN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3872-3875
[20]   A new environmentally friendly method for the production of 2,3,5-trimethyl-p-benzoquinone [J].
Kholdeeva, OA ;
Trukhan, NN ;
Vanina, MP ;
Romannikov, VN ;
Parmon, VN ;
Mrowiec-Bialon, J ;
Jarzebski, AB .
CATALYSIS TODAY, 2002, 75 (1-4) :203-209