188663-32-3

Upstream product

• 188663-05-0 4-[(dimethylamino)methylene]-2-methyl-5(4H)-oxazolone 
• 127143-19-5 N-(5-benzoyl-6-methyl-2-oxo-2H-pyran-3-yl)benzamide 
• 925933-04-6 3-amino-5-benzoyl-6-methyl-2H-pyran-2-one 
• 75-36-5 acetyl chloride 
• 173345-08-9 methyl (Z)-2-acetylamino-3-(dimethylamino)propenoate 
• 93-91-4 1-phenylbutan-1,3-dione 

Downstream Products

• 1257099-67-4 N-[5-benzoyl-2-(diethylamino)-3,4-dimethylphenyl]acetamide 
• 1257099-70-9 N-{5-[(1Z)-3-(diethylamino)-1,2-dimethyl-3-oxoprop-1-enyl]-6-phenyl-2-oxo-2H-pyran-3-yl}acetamide 

Relevant academic research and scientific papers

5-acyl-2H-pyran-2-ones in the schmidt reaction: Migration of the pyran-2-one ring

The Schmidt reaction of the 5-acyl-2H-pyran-2-ones (1a-f) using NaN3/H2SO4 was investigated. The reaction proceeded with complete regioselectivity in the 5-acetyl series to give the corresponding 5-acetylamino derivatives (2a-c) via pyran-2-one ring migra

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

Methyl (Z)-2-acctylamino-3-dimethylaminopropenoate (3) was prepared from N-acetylglycine (1), which was converted with N,N-dimethylfonnamide and phosphorus oxychloride into 4-dimethylaminomethylene-2-methyl-5(4H)-oxazolone (2), followed by treatment with methanol in the presence of potassium carbonate, into 3 The compound 3 was shown to be a versatile reagent in the synthesis of various heterocyclic systems. With N-nucleophiles, such as heterocyclic amines 4, either methyl 2-acetylamino-3-heteroarylaminopropenoates 5 or fused pyrimidinones 6 were formed, dependent on the reaction conditions and/or heterocyclic substituent: C-nucleophiles with an active or potentially active methylene group, such as 1,3-dicarbonyl compounds 7, 8 and 9, substituted phenols 10a,b, naphthols 11,12a-c, and substituted coumarin 13a, afforded substituted pyranones 20 and 22, and fused pyranones 21, 23-26. The nitrogen containing heterocycles 14-19 produced pyranoazines 27-31 and pyranoazole 32. In all of these systems the acetylamino group is attached at position 3 of the newly formed pyranone ring. The orientation around the double bond for methyl (Z)-2-(N-methyl-N-trifluoroacetyl)-3-dimethylaminopropenoate (36) was established by X-ray analysis.