The reaction of N-cyanoamines with 1-(t-butyl)-3,3-diphenylaziridinone: A general method for the synthesis of 1-alkyl-, 1-aralkyl- and 1-aryl-5,5-diphenylhydantoins and -glycocyamidines

N-Cyanomanines react with aziridinone1 to yield the amides2. Base catalysed ring closure of the latter furnished the glycocyamidines3. Acid catalysed de-t-butylation, and deimination combined with de-t-butylation of the compounds3 leads to 1-substituted 5,5-diphenylglycocyamidines (4) and -hydantoins (5), respectively. Part of the hydantoins5 were also directly obtained by hydrochloric acid treatment of amides2. Selective de-t-butylation in position 3 of the glycocyamidine3 (R = t-Bu) was brought about by heating with methanolic NH₃ in the presence of NH₄I. Reaction of1 with the un substituted N-cyanoamine furnished carbodiimide7 which was cyclized to the glycocyamidine8. The mass spectra of some glycocyamidines4 and hydantoins5, as well as of compounds7 and8 are discussed.