173345-07-8Relevant academic research and scientific papers
Nitrosation of methyl 2-acylamino-3-dimethylaminopropenoates. A simple conversion of N-acylglycines into 5-substituted 1,2,4-oxadiazole-3-carboxylates
Kmetic,Stanovnik
, p. 1563 - 1565 (1995)
A novel simple synthesis of 5-substituted-1,2,4-oxadiazole-3-carboxylates 5 from N-acylglycines 1, which are transformed with DMF in the presence of phosphorus oxychloride into 2-substituted-4-dimethylaminomethyleneoxazol-5(4H)-ones 2, followed by opening
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.
