Electrochemical oxidation of 2,3-dimethylhydroquinone in the presence of 1,3-dicarbonyl compounds

被引：58

作者：

Davarani, SSH ^{[1
]}

Nematollahi, D

Shamsipur, M

Najafi, NM

Masoumi, L

Ramyar, S

机构：

[1] Shahid Beheshti Univ, Dept Chem, Tehran, Iran

[2] Univ Bu Ali Sina, Fac Sci, Dept Chem, Hamadan 65174, Iran

[3] Razi Univ, Dept Chem, Kermanshah, Iran

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 05期

关键词：

D O I：

10.1021/jo0523767

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrooxidation of 2,3-dimethylhydroquinone (1) has been studied in the presence of 2-phenyl-1,3-indandione(3a), 3-hydroxy-1H-phenalen-1-one (3b), and 2-chloro-5,5-dimethyl-1,3-cyclohexanedione (3c) as CH acid nucleophiles in water/acetonitrile (85/15) solution, using cyclic voltammetry and controlled-potential coulometry. The results indicate that p-benzoquinone, generated by electrochemically driven oxidation of the 2,3-dimethylhydroquinone (1), is scavenged by 3a-c, to give related products (5a, 9b, 8c) via various electrochemical mechanisms. The electrochemical syntheses of 5a, 9b, and 8c have been successfully performed in one-pot in an undivided cell using an environmentally friendly method with high atomic economy.

引用

页码：2139 / 2142

页数：4

共 27 条

[1] New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp. [J].

Abdel-Lateff, A ;

König, GM ;

Fisch, KM ;

Höller, U ;

Jones, PG ;

Wright, AD .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (11) :1605-1611

[2] Two novel cytotoxic benzofuran derivatives from Brazilian propolis [J].

Banskota, AH ;

Tezuka, Y ;

Midorikawa, K ;

Matsushige, K ;

Kadota, S .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (09) :1277-1279

[3]

Bard A. J., 2001, ELECTROCHEMICAL METH, P497

[4] 4-(2-[2-(2(R)-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H3 receptor antagonists potently enhance cognition and attention [J].

Cowart, M ;

Faghih, R ;

Curtis, MP ;

Gfesser, GA ;

Bennani, YL ;

Black, LA ;

Pan, LP ;

Marsh, KC ;

Sullivan, JP ;

Esbenshade, TA ;

Fox, GB ;

Hancock, AA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (01) :38-55

[5]

GANAPATI DY, 2005, IND ENG CHEM RES, V44, P7969

[6]

Gaszner Peter, 2004, Neuropsychopharmacol Hung, V6, P210

[7] Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure-activity relationships [J].

Hayakawa, I ;

Shioya, R ;

Agatsuma, T ;

Furukawa, H ;

Sugano, Y .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (13) :3411-3414

[8]

Izutsu K., 2002, ELECTROCHEMISTRY NON, P247

[9] Furoyl and benzofuroyl pyrroloquinolones as potent and selective PDE5 inhibitors for treatment of erectile dysfunction [J].

Jiang, WQ ;

Sui, ZH ;

Macielag, MJ ;

Walsh, SP ;

Fiordeliso, JJ ;

Lanter, JC ;

Guan, JH ;

Qiu, YH ;

Kraft, P ;

Bhattacharjee, S ;

Craig, E ;

Haynes-Johnson, D ;

John, TM ;

Clancy, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (03) :441-444

[10] Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase.: Part 3 [J].

Kawasaki, K ;

Masubuchi, M ;

Morikami, K ;

Sogabe, S ;

Aoyama, T ;

Ebiike, H ;

Niizuma, S ;

Hayase, M ;

Fujii, T ;

Sakata, K ;

Shindoh, H ;

Shiratori, Y ;

Aoki, Y ;

Ohtsuka, T ;

Shimma, N .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (01) :87-91

← 1 2 3 →