111256-82-7Relevant academic research and scientific papers
Synthesis of 3-Ω-aminohydantoins
Ryczek, Jozef
, p. 997 - 1000 (2007/10/03)
Several 3-Ω-amino monosubstituted hydantoins have been obtained in the reaction of isocyanate of glycine ethyl ester with the appropriate aliphatic or aromatic diamine. It was found, that the 3-(aminoaryl) monosubstituted hydantoins may be diazotized and their diazonium salts may be coupled and hydrolysed without changes in the hydantoin ring.
MECHANISM OF BASE-CATALYZED CYCLIZATION OF ETHYL N-(SUBSTITUTED AMINOCARBONYL)GLYCINATES
Mindl, Jaromir,Sterba, Vojeslav
, p. 156 - 161 (2007/10/02)
The cyclization rate constants have been measured of substituted ethyl N-(phenylaminocarbonyl)-, N-(alkylaminocarbonyl)-, and N-(phenylaminothiocarbonyl)glycinates RNHCXNHCH2CO2C2H5 (X=O,S).Logarithms of these constants increase with decreasing basicity of the amines down to the value of pKa(RNH2) = 5.5.The rate-limiting step of the reaction is formation of the tetrahedral intermediate.With ethyl N-(phenylaminocarbonyl)glycinates (whose pKa(RNH2) values are higher) this dependence, on the contrary, slightly decreases, and the acid-catalyzed splitting off of ethoxy group from the cyclic intermediate becomes rate-li miting.The cyclization rate of a series of ethyl N-(phenylaminothiocarbonyl)glycinates is practically independent of the pKa(RNH2) values, the change in the rate limiting step would take place at pH about 9.
