Electroorganic synthesis of new benzofuro[2,3-d]pyrimidine derivatives

被引:93
作者
Nematollahi, D [1 ]
Goodarzi, H [1 ]
机构
[1] Univ Bu Ali Sina, Fac Sci, Dept Chem, Hamadan, Iran
关键词
D O I
10.1021/jo0200623
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Electrochemical oxidation of 3,4-dihydroxybenzoic acid (1) in the presence of 1,3-dimethylbarbituric acid (2) and 1,3-diethyl-2-thiobarbituric acid (3) as nucleophiles in aqueous solution has been studied using cyclic voltammetry and controlled-potential coulometry. The results indicate that 1 via Michael reaction under electro-decarboxylation reaction converts to benzofuro[2,3-d]pyrimidine derivatives (6a, 6b). The electrochemical synthesis of 6a, 6b has been successfully performed in an undivided cell in good yields and purity.
引用
收藏
页码:5036 / 5039
页数:4
相关论文
共 37 条
[1]  
Abdel-Rahman A H, 1997, Boll Chim Farm, V136, P262
[2]  
AZZEM MA, 1994, B CHEM SOC JPN, V67, P1390
[3]  
Bard A. J., 2001, ELECTROCHEMICAL METH, P496
[4]   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
[5]  
Brown D. J., 1984, COMPREHENSIVE HETERO, V2, P150
[6]  
BRUN A, 1974, J ELECTROANAL CHEM, V49, P287, DOI 10.1016/S0022-0728(74)80236-6
[7]  
EVANGELISTA S, 1987, DRUG EXP CLIN RES, V13, P501
[8]   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
[9]   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
[10]  
Golabi SM, 1997, B ELECTROCHEM, V13, P156