Facile one-pot synthesis of 5-substituted hydantoins

Abstract

5-Substituted and 5,5-disubstituted hydantoins are synthesised from the corresponding aldehydes or ketones, using a one-pot, gallium(III) triflate-catalysed procedure that is compatible with a range of substrates and solvents.

Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)

“…It is noteworthy that the intensity of peak at δ = 3.92 decreases constantly. Whereas, 1 H NMR spectrum at 40 min shows a very broad peak at δ = 4.69 corresponding to the –NH 3 of intermediate 11 . Interestingly, when the 1 H NMR spectrum was recorded at 45 min both the peaks vanished, which confirms the elimination of ammonia and acetic acid.…”

2-Amino-2-alkyl(aryl)propanenitriles as key building blocks for the synthesis of five-membered heterocycles

“…The kinetically determined pK a values of individual 5-methyl-3,5-diphenylimidazolidin-2,4-diones varied in the range of 11.0-12.1 (water, 25 °C) (Scheme 7). 50 The recently published 51 one-pot methodology of synthesis of hydantoins was realized as a multi-component reaction starting directly from carbonyl compounds, ammonia and carbon dioxide (yields 47-94%). The first step produces the imine, the second step gives the aminonitrile, and the last step provides the required hydantoin.…”

Supramolecular structure of 5-methyl-5-phenyl hydantoin and hydrogen-bonding patterns in 5,5′-substituted hydantoins

“…This multicomponent reaction begins from an aldehyde or a ketone and their ready availability makes this reaction an attractive method for the synthesis of hydantoins [14,22].…”