Mechanism of electrochemical oxidation of catechol and 3-substituted catechols in the presence of barbituric acid derivatives. Synthesis of new dispiropyrimidine derivatives

被引:29
作者
Nematollahi, D [1 ]
Goodarzi, H [1 ]
Tammari, E [1 ]
机构
[1] Univ Bu Ali Sina, Fac Sci, Dept Chem, Hamadan, Iran
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2002年 / 04期
关键词
D O I
10.1039/b106794j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The electrochemical oxidation mechanism of catechol (1a), 3-methylcatechol (1b) and 3-methoxycatechol (1c) in the presence of barbituric acid (3a) and 1,3-dimethylbarbituric acid (3b) as nucleophile in aqueous solution has been studied in detail by cyclic voltammetry and controlled-potential coulometry. The results indicate that 1a-1c via an ECEC (E, electrochemical; C, chemical) pathway, participating in a 1,4 (Michael) addition reaction, are converted to dispiropyrimidine derivatives 6a-6f. The homogeneous rate constants were estimated by comparing the experimental cyclic voltammetric responses with the digital simulated results. The electrochemical synthesis of 6a-6f has been successfully performed in an undivided cell in good yields and high purity.
引用
收藏
页码:829 / 834
页数:6
相关论文
共 36 条
[1]   SYNTHESIS AND ANTI-DNA VIRAL ACTIVITIES IN-VITRO OF CERTAIN 2,4-DISUBSTITUTED-7-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDES [J].
BHATTACHARYA, BK ;
OJWANG, JO ;
RANDO, RF ;
HUFFMAN, JH ;
REVANKAR, GR .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (20) :3957-3966
[2]  
BRUN A, 1974, J ELECTROANAL CHEM, V49, P287, DOI 10.1016/S0022-0728(74)80236-6
[3]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF CERTAIN 3,4-DISUBSTITUTED PYRAZOLO[3,4-D)PYRIMIDINE NUCLEOSIDES [J].
COTTAM, HB ;
PETRIE, CR ;
MCKERNAN, PA ;
GOEBEL, RJ ;
DALLEY, NK ;
DAVIDSON, RB ;
ROBINS, RK ;
REVANKAR, GR .
JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (09) :1119-1127
[4]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF CERTAIN 6-SUBSTITUTED AND 2,6-DISUBSTITUTED 2'-DEOXYTUBERCIDINS PREPARED VIA THE STEREOSPECIFIC SODIUM-SALT GLYCOSYLATION PROCEDURE [J].
COTTAM, HB ;
KAZIMIERCZUK, Z ;
GEARY, S ;
MCKERNAN, PA ;
REVANKAR, GR ;
ROBINS, RK .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (10) :1461-1467
[5]   NITRILES IN ORGANIC-SYNTHESIS - SYNTHESIS OF AROMATIC-AMINES, AMINOPYRIDINES, PYRIDO[2,3-B]PYRIDINE AND PYRIDO[2,3-D]PYRIMIDINE DERIVATIVES [J].
ELTAWEEL, FM .
JOURNAL FUR PRAKTISCHE CHEMIE, 1990, 332 (05) :762-766
[6]  
EVANGELISTA S, 1987, DRUG EXP CLIN RES, V13, P501
[7]   SYNTHESIS OF 5-METHYL-5-DEAZA NONCLASSICAL ANTIFOLATES AS INHIBITORS OF DIHYDROFOLATE REDUCTASES AND AS POTENTIAL ANTIPNEUMOCYSTIS, ANTITOXOPLASMA, AND ANTITUMOR AGENTS [J].
GANGJEE, A ;
SHI, JF ;
QUEENER, SF ;
BARROWS, LR ;
KISLIUK, RL .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) :3437-3443
[8]   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
[9]  
Golabi SM, 1997, B ELECTROCHEM, V13, P156
[10]   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