1049019-27-3Relevant academic research and scientific papers
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
Singh, Kumar K.,Singh, Ram S.,Singh, Radhey M.
, p. 120 - 126 (2007/10/03)
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.
Ethanolysis of 4- (N, N-dimethylaminomemylene)-2-aryl-2-oxazolin-5-ones with sodium ethoxide in ethanol at reflux temperature: Unusual formation of N-acyl-α-amino acids
Singh, Ram S.
, p. 1296 - 1299 (2007/10/03)
The ethanolysis of 4-(N, N - dimethylaminomethylene)-2-aryl-2-oxazolin-5-ones 1 with sodium ethoxide in ethanol at reflux temperature leads to the formation of N-acyl-α-amino acids 3. Further, the reaction of 4-hydroxymethylene-2-phenyl-2-oxazolin-5 one 4 with sodium ethoxide in ethanol at reflux temperature also gives product 3a. The plausible mechanism has been proposed.
