51254-00-3

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1021, 1990 DOI: 10.1002/jhet.5570270439

InChI:InChI=1/C12H12N2O2/c1-14(2)8-10-12(15)16-11(13-10)9-6-4-3-5-7-9/h3-8H,1-2H3/b10-8+

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 56952-04-6 methyl 2-N-benzoylamino-3-N,N-dimethylamino-2-propenoate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 68-12-2 N,N-dimethyl-formamide 
• 6334-93-6 (N-Benzoylglycin)-phenylhydrazid 
• 160692-67-1 N-(2-(2-methoxyphenylamino)-2-oxoethyl)benzamide 
• 92435-03-5 hippuric acid-(3-chloro-anilide) 
• 66924-61-6 N-(2-oxo-2-(o-tolylamino)ethyl)benzamide 
• 34329-56-1 N-(2-((4-methoxyphenyl)amino)-2-oxoethyl)benzamide 
• 51769-53-0 N-<(4-methylphenylamino)carbonylmethyl>benzamide 
• 34329-59-4 N-benzoyl-glycine 4-nitro-anilide 
• 3106-11-4 hippurylanilide 
• 35056-20-3 N-benzoyl-glycine pyridin-2-ylamide 
• 2443-68-7 (2-hydrazinyl-2-oxoethyl)benzamide 

Downstream Products

• 842-74-0 4-benzylidene-2-phenyloxazole-5(4H)-one 
• 125008-68-6 methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate 

Relevant academic research and scientific papers

Transformation of N-acylaminoacetanilides and N-benzoylglycine hydrazides into 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-ones using Vilsmeier-Haack reagent and their reactions with nucleophiles

A convenient one-pot synthesis of 4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-ones (5a-e) has been reported from the reaction of N-acylaminoacetanilides (3a-1) and N-benzoylglycine hydrazides (4a,b) with Vilsmeier-Haack reagent.Compound 5a undergoe

Vilsmeier-Haack reagent: A facile synthesis of 4-heteromethylene-2-aryl-2-oxazolin-5-ones from N-acyl-α-amino acid esters

4-(N,N-dimethylaminomethylene)-2-aryl-2-oxazolin-5-ones (5) have been synthesised from N-acyl-α-amino acid esters (3) by treating with Vilsmeier-Haack reagent, in good yield.The variable temperature-NMR study and a plausible mechanism have also been discu

Methyl 2-Benzoylamino-3-dimethylaminopropenoate in the Synthesis of Fused Pyranones. The Synthesis of Derivatives of Tetrahydro-2H-1-benzopyran-2-one, Isomeric 2H-Naphtholpyran-2-one and 3H-Naphthopyran-3-one, Pyranobenzopyran-2,5-dione, and 7H-Pyranopyrimi...

Methyl 2-benzoylamino-3-dimethylaminopropenoate (1) reacts with carbocyclic and heterocyclic 1,3-diketones or potential 1,3-diketones, such as 1,3-cyclohexanediones 2-4, and 4-hydroxy-2H-1-benzopyran-2-one derivative 17, in acetic acid to afford the corresponding 3-benzoylamino substituted 5-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-2-ones 5-7, and 2H,5H-pyranobenzopyran-2,5-dione derivative 18. 1-Naphthol (12) and 2-naphthol (13) produce the isomeric 2H-naphthopyran-2-one (14) and 3H-naphthopyran-3-one (15) derivatives, respectively.Ethyl cyclopentanone-2-carboxylate (8) and ethyl cyclohexanone-2-carboxylate (9) do not react under these conditions, while in polyphosphoric acid the cyclisation of the reagent 1 is taking place to give 4-dimethylaminomethylene-2-phenyl-5(4H)-oxazolone (10). 4,6-Dihydroxypyrimidine derivative 19 affords in acetic acid the noncyclized intermediate 20, which can be further transformed in polyphosphoric acid into 7H-pyranopyrimidin-7-one derivative 21.

RESEARCH ON AMINOMETHYLENE DERIVATIVES OF AZOLES. 24. CYCLIZATION OF THIOHIPPURIC ACID IN THE PRESENCE OF THE VILSMEIER REAGENT

It is shown that, in contrast to hippuric acid, thiohippuric acid reacts with dimethylformamide in the presence of phosphorus oxychloride to give three compounds, viz., 2-phenyl-4-dimethylaminomethylene-5-thiazolone, 2-phenyl-4-dimethylaminomethyleneoxazo