1-alkylpyrazoles and 1-alkyl-5-chloropyrazoles from halovinyl ketones and 1,1-dialkylhydrazines

被引:11
作者
Bozhenkov, G. N. [1 ]
Savosik, V. A. [1 ]
Klyba, L. V. [1 ]
Zhanchipova, E. R. [1 ]
Mirskova, A. N. [1 ]
Levkovskaya, G. G. [1 ]
机构
[1] Russian Acad Sci, Favorskii Irkutsk Inst Chem, Siberian Div, Irkutsk 664033, Russia
基金
俄罗斯基础研究基金会;
关键词
Pyrazole; Hydrazone; Halogen Atom; Vinyl Ketone; Anhydrous Diethyl Ether;
D O I
10.1134/S1070428008080150
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective heterocyclization of alkyl 2-chloro- and 2,2-dichlorovinyl ketones with 1,1-dialkylhydrazines to 1,3-dialkyl-1H-pyrazoles and 1,3-dialkyl-5-chloro-1H-pyrizoles involves intermediate formation of the corresponding dialkylhydrazones. Fragmentation pattern of chlorine-containing pyrazoles, 3-chloromethyl-1-methyl-1H-pyrazole and 5-chloro-1-methyl-3-propyl-1H-pyrazole, depends on the position of the halogen atom.
引用
收藏
页码:1194 / 1199
页数:6
相关论文
共 17 条
[1]   NEW GENERAL METHODS FOR SUBSTITUTION OF 5-CHLOROPYRAZOLES - SYNTHESIS OF 1,3-DIALKYL-5-CHLOROPYRAZOL-4-YL ARYL KETONES AND NEW 1,3-DIALKYL-2-PYRAZOLIN-5-ONES [J].
BUTLER, DE ;
DEWLAD, H .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (17) :2542-&
[2]  
DEWALD HA, 1974, Patent No. 3823157
[3]  
DEWALD HA, 1975, Patent No. 2423642
[4]  
ELOKHINA VN, 1999, RUSS CHEM B+, P1536
[5]  
Grapov AF, 1999, USP KHIM+, V68, P773
[6]  
IOFFE BV, 1970, KHIM GETEROTSIKL+, P1414
[7]  
KALIKHMA.ID, 1973, B ACAD SCI USSR CH+, P2235
[8]  
KALIKHMAN ID, 1974, IAN SSSR KH, P1402
[9]  
KRASNOSHCHEK AP, 1968, ZH ORG KHIM, V4, P1690
[10]   New synthesis and properties of 3-alkyl-, 3-chloroalkyl-, 3-perfluoroalkyl-, and 3-aryl-1-methyl-(5-halo)pyrazoles from chloro(bromo)vinyl ketones and N,N-dimethylhydrazine [J].
Levkovskaya, GG ;
Bozhenkov, GV ;
Larina, LI ;
Mirskova, AN .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (10) :1501-1506