Abstract

It has been found that 4-nitrophenylglyoxal reacts with N -hydroxyurea both in water and in acetic acid forming the mixture of diastereomers of 3,4,5-trihydroxy-5-(4-nitrophenyl)imidazolidin-2-one. The diastereomer with sic -orientation of OH-groups dominates. In the acetic acid medium 4-nitrophenylglyoxal reacts with 2-methylfuran selectively yielding 2-hydroxy-2-(5-methylfuran-2-yl)-1-(4-nitrophenyl)ethanone

Highlights

  • Arylglyoxals are important precursors in the forming of some heterocyclic compounds[1,2,3,4] but the investigation of such interesting chemical properties of arylglyoxals, as their interaction with N-hydroxyurea[5] and with activated furans,[6] has just recently begun and needs to be continued.Interaction of arylglyoxals with N-hydroxyurea in aqueous medium occurs in three stages and involves the formation of acyclic N-hydroxyureas (1) at the first stage, 5-aryl-3,4,5-trihydroxyimidazolidin-2-ones (2 and 3) at the second stage and 5-aryl-3-hydroxyimidazolidine-2,4-diones (5-aryl-3-hydroxyhydantoins) (4) at the third stage[5] (Scheme 1)

  • We have found that 4-nitrofhenylglyoxal reacts with Nhydroxyurea in aqueous solution at 14°C yielding mixture of diastereomers of 3,4,5-trihydroxy-5-(4-nitrophenyl)imidazolidin-2-one (2g and 3g) (Scheme 4)

  • The reaction of 4-nitrophenylglyoxal with N-hydroxyurea leads to the mixture of diastereomers of 3,4,5-trihydroxy-5(4-nitrophenyl)imidazolidin-2-one

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Summary

Introduction

Arylglyoxals are important precursors in the forming of some heterocyclic compounds[1,2,3,4] but the investigation of such interesting chemical properties of arylglyoxals, as their interaction with N-hydroxyurea[5] and with activated furans,[6] has just recently begun and needs to be continued.Interaction of arylglyoxals with N-hydroxyurea in aqueous medium occurs in three stages and involves the formation of acyclic N-hydroxyureas (1) at the first stage, 5-aryl-3,4,5-trihydroxyimidazolidin-2-ones (2 and 3) at the second stage and 5-aryl-3-hydroxyimidazolidine-2,4-diones (5-aryl-3-hydroxyhydantoins) (4) at the third stage[5] (Scheme 1). Arylglyoxals are important precursors in the forming of some heterocyclic compounds[1,2,3,4] but the investigation of such interesting chemical properties of arylglyoxals, as their interaction with N-hydroxyurea[5] and with activated furans,[6] has just recently begun and needs to be continued. Interaction of arylglyoxals with N-hydroxyurea in aqueous medium occurs in three stages and involves the formation of acyclic N-hydroxyureas (1) at the first stage, 5-. Aryl-3,4,5-trihydroxyimidazolidin-2-ones (2 and 3) at the second stage and 5-aryl-3-hydroxyimidazolidine-2,4-diones (5-aryl-3-hydroxyhydantoins) (4) at the third stage[5] (Scheme 1).

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