Facile entries for regioselective synthesis of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones from 2-thiouracil

被引:11
作者
Shawali, A. S. [1 ]
Abbas, I. M.
Mahran, A. M.
机构
[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
[2] Natl Res Ctr, Giza, Egypt
关键词
heterocycles; hydrazones; rearrangement; synthetic methods; 1,2,4-triazolo-pyrimidine;
D O I
10.1007/BF03245768
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three new alternative synthetic strategies based on reactions of hydrazonoyl halides 3 with 2-methylthiouracil 2 and treatment of either 2-pyrimidinyl thiohydrazonates 8 or the diazonium coupling products of active (pyrimidin-2-ylthio)methylene compounds 12 with sodium ethoxide in ethanol are described for the title compounds. The mechanisms and regiochemistry of the studied reactions are discussed.
引用
收藏
页码:33 / 39
页数:7
相关论文
共 26 条
[1]  
ABARCA B, 1986, J CHEM RES-S, P395
[2]  
Abarca B., 1986, J CHEM RES M, P3358
[3]   REACTIONS WITH 6-METHYL-2-THIOURACIL SYNTHESIS OF DIPYRIMIDINO[2,1-B-1',2'-C]THIAZINE - A NEW RING-SYSTEM [J].
ABDELFATTAH, ASM ;
NEGM, AM ;
GAAFAR, AEM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 72 (1-4) :145-156
[4]  
ALBRIGHT JD, 1980, Patent No. 4209621
[5]  
Atwal KS, 1990, Chem. Abstr., V112, p55902g, Patent No. 3839711
[6]  
Barthelemey G., 1985, Fr. Pat., Patent No. [2549834, 2,549,834]
[7]   N-15 NMR-STUDIES OF GUANIDINES .2. THE FUSED-IN GUANIDINE UNIT OF SOME OXOHETEROCYCLES - A COMBINED N-15 NMR, C-13 NMR AND IR STUDY [J].
BEDFORD, GR ;
TAYLOR, PJ ;
WEBB, GA .
MAGNETIC RESONANCE IN CHEMISTRY, 1995, 33 (05) :389-394
[8]   ISOCYTOSINE H2-RECEPTOR HISTAMINE-ANTAGONISTS .1. OXMETIDINE AND RELATED-COMPOUNDS [J].
BROWN, TH ;
BLAKEMORE, RC ;
DURANT, GJ ;
EMMETT, JC ;
GANELLIN, CR ;
PARSONS, ME ;
RAWLINGS, DA ;
WALKER, TF .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1988, 23 (01) :53-62
[9]  
BRUMAGNIEZ N, 1995, Patent No. 5387747
[10]  
BUNNETT JF, 1958, Q REV LONDON, V12, P12