Transformation of 4-(1-dimethylaminoethylidene)-2-phenyl-5(4H)-oxazolone into methyl 2-benzoylamino-3-oxobutanoate.: The synthesis of 1-substituted 4-benzoylamino-3-methyl-5(2H)-pyrazolones

被引：17

作者：

Bratusek, U ^{[1
]}

Hvala, A ^{[1
]}

Stanovnik, B ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1998年 / 35卷 / 06期

关键词：

D O I：

10.1002/jhet.5570350607

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl 2-benzoylamino-3-oxobutanoate (3) was prepared from hippuric acid (1) which was converted with N,N-dimethylacetamide and phosphorus oxychloride into 4-(1-dimethylaminoethylidene)-2-phenyl-5(4H)-oxazolone (2) followed by hydrolysis with hydrochloric acid in methanol. Compound 3 was treated with hydrazines 4 to give 4-benzoylamino-3-methyl-1H-pyrazol-5(2H)-one (6a) and its 1-substituted derivatives 6b-j. The corresponding hydrazones 5f, i, j were isolated as intermediates.

引用

页码：1281 / 1284

页数：4

共 26 条

[1]

[Anonymous], 1993, PROG HETEROCYCL CHEM, DOI [10.1002/jhet.5570270247z(, DOI 10.1002/JHET.5570270247Z]

[2]

BRATUSEK U, IN PRESS J HETEROCYC

[3] EVALUATION AND SYNTHESIS OF AMINOHYDROXYISOXAZOLES AND PYRAZOLES AS POTENTIAL GLYCINE AGONISTS [J].

DRUMMOND, J ;

JOHNSON, G ;

NICKELL, DG ;

ORTWINE, DF ;

BRUNS, RF ;

WELBAUM, B .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (09) :2116-2128

[4]

ELGUERO J, 1984, PYRAZOLES THEIR BENZ, V5, P167

[5]

ELGUERO J, 1996, PYRAZOLES COMPREHENS, V3, P1

[6] SIMPLE ROUTE TO ALPHA-AMINOKETONES AND RELATED DERIVATIVES BY DIANION ACYLATION REACTIONS - IMPROVED PREPARATION OF DELTA-AMINOLEVULINIC-ACID [J].

EVANS, DA ;

SIDEBOTTOM, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (17) :753-754

[7]

FUSCO R, 1967, PYRAZOLES PYRAZOLINE, P1

[8] HYDROXYALKYLATION AND ACYLATION REACTIONS OF METHYL HIPPURATE [J].

HARDING, KE ;

MORENO, LN ;

NACE, VM .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (13) :2809-2812

[9] Aminoacids in the synthesis of heterocyclic systems. The synthesis of methyl 2-acetylamino-3-dimethylaminopropenoate and 2-(N-methyl-N-trifluoroacetyl)amino-3-dimethylaminopropenoate and their application in the synthesis of heterocyclic compounds [J].

Kralj, L ;

Hvala, A ;

Svete, J ;

Golic, L ;

Stanovnik, B .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (01) :247-255

[10]

KRAPCHO AP, 1976, TETRAHEDRON LETT, P2205

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