50784-69-5

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 28, p. 453, 1991 DOI: 10.1002/jhet.5570280247

InChI:InChI=1/C12H11NO3/c1-2-15-12(14)10-8-13-16-11(10)9-6-4-3-5-7-9/h3-8H,2H2,1H3

Upstream product

• 4474-19-5 N-hydroxyformimidoyl iodide 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 66129-60-0 (E)-ethyl 2-(N,N-dimethylaminomethyliden) benzoylacetate 
• 66129-60-0 ethyl-3-(dimethylamino)-2-(phenylcarbonyl)prop-2-enoate 
• 199672-88-3 (E)-2-Benzoyl-3-(8-methyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-ylamino)-acrylic acid ethyl ester 

Downstream Products

• 76344-95-1 5-phenylisoxazole-4-carboxylic acid 
• 1611-02-5 2-cyano-3-oxo-3-phenyl-propionic acid ethyl ester 
• 136995-29-4 5-phenylisoxazole-4-carbonyl chloride 
• 502935-51-5 5-phenyl-isoxazole-4-carboxylic acid methoxy-amide 
• 14441-90-8 5-phenyl-3-isoxazolecarboxylic acid 

Relevant academic research and scientific papers

Alkyl(E,Z)-2-(2-Benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3- dimethylaminopropenoates in the Synthesis of Fused Pyrimidinones. A Facile Route to 3-Aminoazino-4H-pyrimidin-4-ones

Alkyl (E,Z)-2K2-benzoyl-2-thoxycarbonyl-1-thenyl)amino-3-dimethylaminopropenoates 1a,b react with neteroarylamines 2 to give alkyl 2-(2-benzoyl-2-ethoxycarbonyl-1-ethenyl)amino-3-heteroarylaminopropenoates 3-13. These were cyclized into fused 3-(2-benzoyl-2-etboxycarbonyl-1-ethenyl)amino-4H-azolo- (or azino)-pyrimidin-4-ones 14-18. 2-Benzoyl-2-ethoxycarbonyl-1-ethenyl group can be easily removed from 3-(2-benzoyl-2-ethoxycarbonyl-1ethenyl)amino-8-methyl-4H-pyrido[1,2-a]pyrimidin- 4-one (14) to give 3-amino-8-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (19). The structure of 1a was confirmed by X-ray analysis.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. X. Synthesis of 5-Substituted Ethyl or Methyl 4-Isoxazolecarboxylates and Methyl 4-(2,2-Dimethyl-1-oxopropyl)-5-isoxazolecarboxylate

Reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with hydroxylamine hydrochloride in methanol solution afforded in high yields the relative esters of 5-substituted 4-isoxazolecarboxylic acids II.These esters were hydrolyzed generally with concentrated hydrochloric acid-acetic acid mixtures to the corresponding carboxylic acids in satisfactory yields.Ethyl or methyl esters II isomerized with sodium ethoxide or methoxide, respectively, to the corresponding esters or hemiesters of 2-cyano-3-oxoalkanoic acids generally in excellent to satisfactory yields.Reaction of methyl 5,5-dimethyl-3-dimethylaminomethylene-2,4-dioxohexanoate with hydroxylamine hydrochloride afforded in moderate yield methyl 4-(2,2-dimethyl-1-oxopropyl)-5-isoxazolecarboxylate, which was converted by acid hydrolysis as above to 4-t-butyl-4-hydroxyfuroisoxazol-6-(4H)-one.

5-Aryl-4-isoxazolecarboxylate-safening agents

The invention relates to the safening of crop plants to the use of herbicides using a 5-aryl-4-isoxazolecarboxylate or composition containing such compounds to reduce the herbicidal injury to treated crop plants. The invention is also concerned with novel compositions which comprise an acetanilide herbicide and a 5-aryl-4-isoxazolecarboxylate.