Synthesis of new chiral N-substituted fused pyrazoles and pyrazolinols.

被引:25
作者
Popov, SA
Shakirov, MM
Tkachev, AV
DeKimpe, N
机构
[1] NOVOSIBIRSK ORGAN CHEM INST,NOVOSIBIRSK 630090,RUSSIA
[2] STATE UNIV GHENT,FAC AGR & APPL BIOL SCI,DEPT ORGAN CHEM,B-9000 GHENT,BELGIUM
基金
俄罗斯基础研究基金会;
关键词
D O I
10.1016/S0040-4020(97)10239-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of beta-diketones and the corresponding beta-enaminoketones, having modified carane (2-ethyl-6,6-dimethylbicyclo[3.1.0]hexane) and p-menthane (3-ethyl-1-isopropylcyclopentane) skeletons, with aryl-and alkylhydrazines results in regioselective formation of N-substituted pyrazoles or stable pyrazolinols depending on the nature of the substituent at the hydrazine nitrogen. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:17735 / 17750
页数:16
相关论文
共 14 条
[1]   REGIOSPECIFIC SYNTHESIS OF 1-ARYLPYRAZOLES [J].
ALBEROLA, A ;
ANDRES, C ;
ORTEGA, AG ;
PEDROSA, R .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (05) :1575-1576
[2]   ISOMERIZATIONS AKIN TO DIMROTH REARRANGEMENT .3. CONVERSION OF SIMPLE S-TRIAZOLO[4,3-A]PYRIMIDINES INTO THEIR [1,5-A] ISOMERS [J].
BROWN, DJ ;
NAGAMATSU, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (11) :2515-2525
[3]  
HUNIG S, 1959, LIEBIGS ANN CHEM, V628, P46
[4]   THE PREPARATION OF SUBSTITUTED HYDRAZINES .4. ARYLHYDRAZINES VIA CONVENTIONAL METHODS [J].
HUNSBERGER, IM ;
SHAW, ER ;
FUGGER, J ;
KETCHAM, R ;
LEDNICER, D .
JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :394-399
[5]   Enantiomerically enriched preparation of enolizable beta-keto amides. Diastereoselective alpha-acylation and subsequent aminolysis of 2-acyl-3-phenyl-l-menthopyrazoles [J].
Kashima, C ;
Fukuchi, I ;
Takahashi, K ;
Hosomi, A .
TETRAHEDRON, 1996, 52 (31) :10335-10346
[6]   STEREOSELECTIVE N-ACYLATION OF A NEW CHIRAL AUXILIARY COMPOUND - 3-PHENYL-L-MENTHOPYRAZOLE [J].
KASHIMA, C ;
FUKUCHI, I ;
TAKAHASHI, K ;
HOSOMI, A .
TETRAHEDRON LETTERS, 1993, 34 (51) :8305-8308
[7]  
PERKIN WH, 1913, J CHEM SOC, V103, P1978
[8]   NEW CHIRAL AGENTS FOR RESOLUTION OF RACEMIC CIS-PERMETHRIC AND CIS-Z-CYHALOTHRIC ACIDS [J].
POPOV, SA ;
TKACHEV, AV .
TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :1013-1018
[9]   SYNTHESIS OF NEW CHIRAL HETEROCYCLES OF THE PYRAZOLE AND 2-ISOXAZOLINE TYPES FROM (+)-3-CARENE [J].
POPOV, SA ;
YU, A ;
DENISOV, AY ;
GATILOV, YV ;
BAGRYANSKAYA, IY ;
TKACHEV, AV .
TETRAHEDRON-ASYMMETRY, 1994, 5 (03) :479-489
[10]  
SHIRAKAWA K, 1963, TAKEDA KENKYUSHO NEM, V22, P19