Electrochemical study of catechols in the presence of 4,6-dihydroxy-2-methylpyrimidine

被引：18

作者：

Fakhari, AR ^{[1
]}

Nematollahi, D

Moghaddam, AB

机构：

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

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

来源：

JOURNAL OF ELECTROANALYTICAL CHEMISTRY | 2005年 / 577卷 / 02期

关键词：

cyclic voltammetry; electro-organic synthesis; catechols; benzofuro[2,3-d]pyrimidine derivatives; o-benzoquinones;

D O I：

10.1016/j.jelechem.2004.11.032

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

Electrochemical oxidation of catechol (1a), 3-methylcatechol (1b), and 3-methoxycatechol (1c) has been studied in the presence of 4,6-dihydroxy-2-methylpyrimidine (3) as a nucleophile in aqueous solution using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from catechols (1a-1c) participate in Michael addition reactions with 3 to form the corresponding benzofuro[2,3-d]pyrimidine derivatives (6a-6c). The electrochemical synthesis of (6a-6c) has been successfully performed in an undivided cell in good yield and purity. The mechanism of oxidation was deduced from voltammetric data and by coulometry at controlled-potential. The products have been characterized after purification by IR, H-1 NMR, C-13 NMR and MS. (c) 2004 Elsevier B.V. All rights reserved.

引用

页码：205 / 210

页数：6

共 25 条

[1] NUANCES OF ECE MECHANISM .2. ADDITION HYDROCHLORIC ACID AND AMINES TO ELECTROCHEMICALLY GENERATED O-BENZOQUINONES [J].

ADAMS, RN ;

HAWLEY, MD ;

FELDBERG, SN .

JOURNAL OF PHYSICAL CHEMISTRY, 1967, 71 (04) :851-&

[2]

AZZEM MA, 1994, B CHEM SOC JPN, V67, P1390

[3]

BATTACHARY BK, 1998, J MED CHEM, V38, P3957

[4]

BRUN A, 1974, J ELECTROANAL CHEM, V49, P287, DOI 10.1016/S0022-0728(74)80236-6

[5] Electrochemical study of 3,4-dihydroxybenzoic acid and 4-tert-butylcatechol in the presence of 4-hydroxycoumarin - Application to the electro-organic synthesis of coumestan derivatives [J].

Golabi, SM ;

Nematollahi, D .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1997, 430 (1-2) :141-146

[6] Electrochemical study of catechol and some 3-substituted catechols in the presence of 4-hydroxy coumarin: Application to the electro-organic synthesis of new coumestan derivatives [J].

Golabi, SM ;

Nematollahi, D .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1997, 420 (1-2) :127-134

[7] ELECTROCHEMICAL STUDIES OF OXIDATION PATHWAYS OF CATECHOLAMINES [J].

HAWLEY, MD ;

TATAWAWA.SV ;

PIEKARSK.S ;

ADAMS, RN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :447-&

[8]

KAKIYA H, 2002, J AM CHEM SOC, V31, P124

[9] Regiospecific synthesis of 3-substituted imidazo[1,2-a]pyridines, imidazo[1,2-a]pyrimidines, and imidazo[1,2-c]pyrimidine [J].

Katritzky, AR ;

Xu, YJ ;

Tu, HB .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4935-4937

[10] Novel syntheses of 2,3-disubstituted benzofurans [J].

Katritzky, AR ;

Ji, Y ;

Fang, Y ;

Prakash, I .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5613-5615

← 1 2 3 →