125732-40-3

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 2087, 1989 DOI: 10.1080/00397918908052602

Upstream product

• 570-08-1 diethyl acetylmalonate 
• 5456-14-4 3,5-diethoxy-carbonyl-2,6-dimethyl-4H-pyran-4-one 
• 105-53-3 diethyl malonate 
• 102626-05-1 ethyl 3-amino-2-phenylaminocarbonyl-2-butenoate 
• 137786-67-5 ethyl 3-amino-2-ethoxycarbonyl-2-butenoate 
• 31575-84-5 (1-hydroxyethylidene)malonic acid diethyl ester 

Downstream Products

• 1288961-01-2 3-(2,4-dichlorophenyl)-6-methylpyrazolo[5,1-b][1,3]oxazole-7-carboxylic acid 
• 1288960-98-4 ethyl 3-(2,4-dichlorophenyl)-6-methylpyrazolo[5,1-b][1,3]oxazole-7-carboxylate 
• 1207259-65-1 3-[2-(2,4-dimethyl-phenyl)-1-methyl-2-oxo-ethoxy]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

1,5,7-TRISUBSTITUTED ISOQUINOLINE DERIVATIVES, PREPARATION THEREOF, AND USE THEREOF IN MEDICINES

The present disclosure relates to 1,5,7-trisubstituted isoquinoline derivatives, their preparation and pharmaceutical use. In particular, the present disclosure discloses a compound of formula (I) or a pharmaceutically acceptable salt, stereoisomer, solvate or prodrug thereof, and a preparation method and use thereof. The definitions of the groups in the formula can be found in the specification and claims.

PYRAZOLOOXAZOLE COMPOUND

A compound represented by the formula (I) or pharmacologically acceptable salt thereof exhibits an excellent CRF receptor antagonism. wherein R1 and R2 are the same or different and are a hydrogen atom, a C1-6 alkyl group, a cyclic group selected from a C3-6 cycloalkyl group, a tetrahydropyranyl group, a dihydropyranyl group, a tetrahydrofuryl group, a dioxanyl group, a tetrahydrothienyl group, a dithianyl group and a hexahydrothiepinyl group, a C1-6 alkyl group substituted with a cyclic group selected from a C3-6 cycloalkyl group, a tetrahydropyranyl group, a dihydropyranyl group, a tetrahydrofuryl group, a dioxanyl group, a tetrahydrothienyl group, a dithianyl group and a hexahydrothiepinyl group, etc; R3, R4 and R5 are the same or different and are a hydrogen atom, a C1-6 alkyl group, a C3-6 cycloalkyl group, a C1-6 alkoxy group, a C1-6 alkoxy-C1-6 alkyl group, a C3-6 cycloalkoxy-C1-6 alkyl group or a halogen atom; R6 is a hydrogen atom or a C1-6 alkyl group; and R7 is a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkylthio group.

Organic compounds

There are described pyrazolo[5.1-b]oxazole derivatives useful as corticotropin releasing factor (CRF1) receptor antagonists.

Efficient synthesis of 4-ethoxycarbonyl pyrazolin-5-one derivatives

Concise and efficient methods for the preparation of 3-substituted 4-ethoxycarbonylpyrazolin-5-ones are described. The synthetic strategies involve carbon-acylation in the presence of base, followed by ring cyclization with hydrazine or hydrazine monohydrochloride.

Synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones

The synthesis of 3-substituted and 3,4-disubstituted pyrazolin-5-ones from acylated ethyl acetoacetates and diethyl malonates is described. The reaction of acylated ethyl acetoacetates and diethyl acetylmalonate with hydrazine (98%) gave 3-substituted pyrazolin-5-ones and malonyldihydrazide, respectively, following a deacetylation-condensation sequence. The reaction of ethyl 2-acetyl-3-hydroxy-2-butenoate and diethyl 2-(1-hydroxyethylidene)malonate with hydrazine monohydrochloride yielded ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate and 4-ethoxycarbonyl-3-methylpyrazolin-5-one, respectively, following a dehydration-cyclocondensation sequence, in high yields.

THE SELECTIVE METHYLATION OF 4-ETHOXYCARBONYL-3-METHYLPYRAZOLIN-5-ONE WITH DIMETHYL SULFATE

The methylation of some pyrazolin-5-ones with dimethyl sulfate in different reaction conditions is described.It is found that it is possible achived selective introducing of methyl group in desired position of pyrazolin-5-one ring which is of great interest for preparation of many analgesics and antipyretics with pyrazolin-5-one unit.