THE REFORMATSKY REACTION OF 1-ACYL-3,5-DIMETHYLPYRAZOLES - A CONVENIENT PREPARATION OF 4-AMINO-3-OXOALKANOIC ACID-DERIVATIVES

被引:29
作者
KASHIMA, C
KITA, I
TAKAHASHI, K
HOSOMI, A
机构
[1] Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki
关键词
D O I
10.1002/jhet.5570320303
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The conversion of N-acylpyrazoles into beta-keto esters was accomplished efficiently by the treatment with alpha-bromo esters and zinc dust. Using this Reformatsky reaction of N-acylpyrazoles, 4-protected amino)-3-oxoalkanoic acid derivatives were conveniently prepared as the key intermediates in the synthesis of statines.
引用
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页码:723 / 725
页数:3
相关论文
共 7 条
[1]   SYNTHESIS OF BETA-KETO-ESTERS BY THE REFORMATSKY REACTION OF 3-ACYLOXAZOLIDIN-2-ONES AND 3-ACYLTHIAZOLIDINE-2-THIONES [J].
KASHIMA, C ;
HUANG, XC ;
HARADA, Y ;
HOSOMI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (03) :793-794
[2]  
KASHIMA C, 1994, SYNTHESIS-STUTTGART, P61
[3]   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
[4]   AMINOLYSIS OF N-ACYLPYRAZOLES [J].
KASHIMA, C ;
FUKUCHI, I ;
TAKAHASHI, K ;
HOSOMI, A .
HETEROCYCLES, 1994, 38 (06) :1407-1412
[5]   DIASTEREOSELECTIVE ALPHA-ALKYLATION OF 2-ACYL-3-PHENYL-L-MENTHOPYRAZOLES [J].
KASHIMA, C ;
FUKUCHI, I ;
HOSOMI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7821-7824
[6]   CHEMOSELECTIVE PREPARATION OF KETONES BY THE GRIGNARD REACTION OF N-ACYLPYRAZOLES [J].
KASHIMA, C ;
KITA, I ;
TAKAHASHI, K ;
HOSOMI, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (01) :25-27
[7]   A FACILE SYNTHESIS OF STATINE AND ANALOGS BY REDUCTION OF BETA-KETO-ESTERS DERIVED FROM BOC-PROTECTED AMINO-ACIDS - HPLC ANALYSES OF THEIR ENANTIOMERIC PURITY [J].
MAIBAUM, J ;
RICH, DH .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :869-873