14848-36-3

Upstream product

• 107872-68-4 2-benzoylamino-3-chloro-acrylic acid 
• 538-75-0 dicyclohexyl-carbodiimide 
• 65037-88-9 2-phenyl-4-(hydroxymethylidene)-5(4H)-oxazolone 
• 495-69-2 Hippuric Acid 
• 125008-68-6 methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate 
• 108-24-7 acetic anhydride 
• 33646-32-1 methyl 2-benzamido-3-chloro-propanoate 
• 182930-16-1 (Z)-4-(N,N-dimethylaminomethylene)-2-phenyl-2-oxazolin-5-one 
• 1049019-27-3 4-hydroxymethylidene-2-phenyl-4,5-dihydrooxazol-5-one 

Downstream Products

• 94538-54-2 4-(3,5-dimethyl-pyrrol-2-ylmethylene)-2-phenyl-4H-oxazol-5-one 
• 92060-61-2 (E)-4-((1H-pyrrol-2-yl)methylene)-2-phenyloxazol-5(4H)-one 
• 449-81-0 (4Z)-2-phenyl-4-[(4-fluorophenyl)methylidene]-1,3-oxazol-5(4H)-one 
• 95223-60-2 (Z)-4-(4-phenoxybenzylidene)-2-phenyloxazol-5(4H)-one 
• 91371-35-6 2-phenyl-4-(2,3,3-trichloro-allyliden)-4H-oxazol-5-one 
• 121734-46-1 2,4-dimethyl-5-(5-oxo-2-phenyl-oxazol-4-ylidenemethyl)-pyrrole-3-carboxylic acid ethyl ester 
• 1564-29-0 (Z)-4-[4-(dimethylamino)benzylidene]-2-phenyloxazol-5(4H)-one 
• 101272-52-0 2-benzoylamino-3-chloro-acrylic acid anilide 
• 15601-44-2 (Z)-2-phenyl-4-(4-chlorobenzylidene)-5(4H)-oxazolone 
• 101727-65-5 2-phenyl-4-((Z)-3,4,5-trihydroxy-benzyliden)-4H-oxazol-5-one 
• 712-64-1 4-fluoromethylene-2-phenyl-4H-oxazol-5-one 
• 98947-28-5 2-benzoylamino-3-chloro-acrylic acid amide 
• 107872-68-4 2-benzoylamino-3-chloro-acrylic acid 
• 109475-44-7 6-benzoylamino-2,2-dimethyl-5-oxo-2,3,4,5-tetrahydro-[1,4]thiazepine-3-carboxylic acid 

Relevant academic research and scientific papers

Oxazolone copper(I) complexes inspired by the methanobactin active site

Two oxazolone-derived potential ligands with enethioether substituents have been synthesized that differ by the terminal thioether moiety (S-Et in L 1, S-C6H4(OMe)-2 in L2). Both L 1 and L2 behave as bidentate {NS} chelate ligands to form stable complexes with copper(I) triflate that crystallize as dimeric complexes [L2Cu2(OTf)2] (4 and 5) featuring a central {Cu2S2} diamond core with distinctly different Cu-S bonds. L1 as well as 4 and 5 have been characterized by single crystal X-ray diffraction. NMR spectroscopy including 1H and 19F DOSY experiments reveals that 4 and 5 dissociate into monomeric species [LCu(OTf)] (4′ and 5′) in CDCl3 solutions. 4′ and 5′ retain the {NS} binding motif of the oxazolone-derived ligands, but are in slow equilibrium with their {OS} isomers 4″ and 5″ that result from E/Z isomerization of the exocyclic enethioether double bond.

Unusual reactions of 2-aryl-4-(N,N-dimethylaminomethylene)-2-oxazolin5-ones with O-nucleophiles: Synthesis of 2-aryl-4-hydi oxymethylene- 2-oxazolin-5-ones

The reactions of 2-aryl-4-(N,N-dimethyIaminomethylene)-2- oxazolin-5-ones 2 with aqueous or ethanolic KOH and sodium ethoxide lead to the formation of 2-aryl-4-hydroxymethylene-2-oxazolin-5ones 4, 1,5-bond remaining unaffected. However, the reactions of 2 with aqueous or methanolic KOH afford methyl 2-acylamino-3-dimethylaminopropenoates 9 along with 4. These observations are explained by the hard-soft acid-base (HSAB) principle. Further, compounds 9 on treatment with POCl3 in pyridine and ethanolic KOH give the corresponding cyclized products 2 and 4, respectively.