5871-79-4Relevant academic research and scientific papers
Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides
Hillier, Michael C.,Gong, Hai-Hua,Clyne, Dean S.,Babcock, Martin J.
, p. 9413 - 9420 (2014)
The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin.
