Carbon disulfide promoted reactions of 2-chloro-4,5-dihydro-imidazole with some N-nucleophiles

被引:12
作者
Saczewski, F [1 ]
Saczewski, J
Gdaniec, M
机构
[1] Med Univ Gdansk, Dept Chem Technol Drugs, PL-80416 Gdansk, Poland
[2] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland
关键词
2-chloro-4,5-dihydroimidazole; carbon disulfide; nucleophilic substitution; N-nucleophiles; 2-(4,5-dihydroimidazol-2-yl)-1H-indazole; X-ray analysis;
D O I
10.1248/cpb.49.1203
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The reactions of 2-chloro-4,5-dihydroimidazole I with o-substituted anilines and azoles promoted by carbon disulfide have been carried out. Ab initio MO calculations were used to elucidate the mechanism of the reaction of 1 with N-nucleophilic reagents. A facile synthesis of 2-(4,5-dihydroimidazol-2-yl)-1H-indazole 3e bearing structural resemblances to 2-BFI, a potent and selective agonist of imidazoline I-2 receptors, is also described. Structure of 3e was confirmed by NMR spectroscopy and X-ray analysis.
引用
收藏
页码:1203 / 1206
页数:4
相关论文
共 26 条
[1]  
CLARK RD, Patent No. 5726197
[2]   Imidazoline receptors: From discovery to antihypertensive therapy (facts and doubts) [J].
Farsang, C ;
Kapocsi, J .
BRAIN RESEARCH BULLETIN, 1999, 49 (05) :317-331
[3]  
HUDSON AL, 1995, BRIT J PHARMACOL, V114, pP411
[4]   SYNTHESIS AND STRUCTURE ACTIVITY RELATIONSHIP OF NEW CEPHALOSPORINS WITH AMINO HETEROCYCLES AT C-7 - DEPENDENCE OF THE ANTIBACTERIAL SPECTRUM AND BETA-LACTAMASE STABILITY ON THE PKA OF THE C-7 HETEROCYCLE [J].
JUNG, F ;
DELVARE, C ;
BOUCHEROT, D ;
HAMON, A ;
ACKERLY, N ;
BETTS, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :1110-1116
[5]  
KATRITZKY AR, 1990, SYNTHESIS-STUTTGART, P561
[6]  
KOSASAYAMA A, 1979, CHEM PHARM BULL, V27, P831
[7]  
Kuma Diffraction, 2000, KUMA DIFFRACTION KM4
[8]  
MATSUO M, 1985, CHEM PHARM BULL, V33, P4409
[9]  
MOLNAR J, 1985, Patent No. 4526898
[10]  
OKADA M, Patent No. 0209863