4-TRIFLUOROMETHYLIMIDAZOLE AND 5-TRIFLUOROMETHYLIMIDAZOLE - NOVEL CYCLIZATION OF TRIFLUOROACETYLATED ALDEHYDE DIMETHYLHYDRAZONES

被引:20
作者
KAMITORI, Y
HOJO, M
MASUDA, R
OHARA, S
KAWASAKI, K
KAWAMURA, Y
TANAKA, M
机构
[1] Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Kobe
关键词
D O I
10.1002/jhet.5570270303
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thermally induced cyclization reaction of trifluoroacetylated arylaldehyde dimethylhydrazones 1 in refluxing toluene afforded 1‐methyl‐4‐aryl‐5‐trifluoromethylimidazoles 2 in good yields. In contrast thermal cyclization of 1 in the presence of silica gel gave regioisomeric 1‐methyl‐4‐trifluoromethyl‐5‐aryl‐imidazoles 5 as major products. These reactions could be extended to the syntheses of related several 1,4,5‐trisubstituted imidazoles. Copyright © 1990 Journal of Heterocyclic Chemistry
引用
收藏
页码:487 / 495
页数:9
相关论文
共 7 条
[1]   THE UNUSUAL CYCLIZATION OF BENZIL MONOHYDRAZONES TO 4,5-DIPHENYLIMIDAZOLES [J].
COLLIBEE, WL ;
ANSELME, JP .
TETRAHEDRON LETTERS, 1985, 26 (13) :1595-1596
[2]  
DOMNIN NA, 1958, ZH OBSHCH KHIM+, V28, P1550
[3]  
FILLAR R, 1979, ORGANOFLUORINE CHEM
[4]   CONVENIENT SYNTHESIS OF 4-TRIFLUOROMETHYLPYRAZOLES BY CYCLIZATION OF TRIFLUOROACETYLATED HYDRAZONES [J].
KAMITORI, Y ;
HOJO, M ;
MASUDA, R ;
OHARA, S ;
KAWASAKI, K ;
YOSHIKAWA, N .
TETRAHEDRON LETTERS, 1988, 29 (41) :5281-5284
[5]  
KAMITORI Y, 1988, SYNTHESIS-STUTTGART, P208
[6]   ELECTROPHILIC SUBSTITUTION-REACTION AT AZOMETHINE CARBON-ATOM - ACYLATION OF ALIPHATIC ALDEHYDE HYDRAZONES [J].
KAMITORI, Y ;
HOJO, M ;
MSUDA, R ;
YOSHIDA, T ;
OHARA, S ;
YAMADA, K ;
YOSHIKAWA, N .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :519-526
[7]   ELECTROPHILIC SUBSTITUTION AT AZOMETHINE CARBON-ATOMS - REACTION OF AROMATIC ALDEHYDE HYDRAZONES WITH TRIFLUOROACETIC-ANHYDRIDE [J].
KAMITORI, Y ;
HOJO, M ;
MASUDA, R ;
FUJITANI, T ;
OHARA, S ;
YOKOYAMA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :129-135