Electro-oxidation of 3,4-dihydroxybenzoic acid in the presence of 6-methyl-1,2,4-triazine-3-thione-5-one: Unique synthesis of 7H-Thiazolo[3,2-b]-1,2,4-triazin-7-one derivative in aqueous media

被引：6
作者：
Fotouhi, Lida [1 ]
Nematollahi, Davood [2 ]
Heravi, Majid M. [1 ]
机构：
[1] Alzahra Univ, Fac Sci, Dept Chem, Tehran, Iran
[2] Bu Ali Sina Univ, Fac Sci, Dept Chem, Hamadan, Iran
来源：
JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2007年 / 54卷 / 05期
关键词：
electrochemical oxidation; Michael addition; quinone; 6-methyl-1,2,4-triazine-3-thion-5-one;
D O I：
10.1002/jccs.200700166
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The electrochemical oxidation of 3,4-dihydroxy benzoic acid (1) has been studied in the presence of 6-methyl-1,2,4-triazine-3-thione-5-one (2) in aqueous solution. The oxidation mechanism of 1 and its reaction in the presence of 2 was offered. It was confirmed that 1 is converted to 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivative 5 through Michael addition reaction of 2 to anodically generated o-benzoquinone. The results of the research were used for electrochemical synthesis of 5 in an undivided cell in good yield and purity.
引用
收藏
页码：1163 / 1166
页数：4
相关论文
共 22 条
[1]   N-oxidation of pyridine carboxylic acids using hydrogen peroxide catalyzed by a green heteropolyacid catalyst:: Preyssler's anion, [NaP5W30O110]14- [J].
Bamoharram, Fatemeh F. ;
Heravi, Majid M. ;
Roshani, Mina ;
Tavakoli, Niloofar .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 252 (1-2) :219-225
[2]  
Bard A. J., 2001, ELECTROCHEMICAL METH, V2nd, P512
[3]  
BARTLETT RR, 1989, DRUG EXP CLIN RES, V15, P521
[4]  
DOLESCHALL G, 1967, ACTA CHIM HUNG, V53, P385
[5]   An efficient electrochemical method for a unique synthesis of new derivatives of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one [J].
Fotouhi, L ;
Nematollahi, D ;
Heravi, MM ;
Tammari, E .
TETRAHEDRON LETTERS, 2006, 47 (11) :1713-1716
[6]   Voltammetric oxidation of Hantzsch 1,4-dihydropyridines in ethanol-water media [J].
Fotouhi, L ;
Khaleghi, S ;
Heravi, MM .
LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (02) :111-114
[7]   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
[8]  
HERAVI M, 1992, IRAN J CHEM CHEM ENG, V11, P8
[9]  
Heravi M.M., 2006, J MOL CAT CHEM A, V1, P249
[10]   12-molybdophosphoric acid: A recyclable catalyst for the synthesis of Biginelli-type 3,4-dihydropyrimidine-2(1H)-ones [J].
Heravi, Majid M. ;
Bakhtiari, Khadijeh ;
Bamoharram, Fatemeh F. .
CATALYSIS COMMUNICATIONS, 2006, 7 (06) :373-376
123