One-pot synthesis of the substituted imidazolidin-2-ones with participation of thiobarbituric acid, ureas and arylglyoxals

N M Kolos,L L Zamigaylo,N V Chechina

doi:10.24959/ophcj.13.742

Abstract

Derivatives of imidozoline-2-ones containing the pyrimidinthionic moiety in position 4 have been synthesized by three-component one-pot condensation of thiobarbituric acid, arylglyoxal hydrates and ureas. It has been found that these compounds exist in the solution of DMSO-d6 as a mixture of two tautomeric forms: for products obtained from N-substituted ureas the imidazolidin form predominates; and in the case of urea the imidazolidin and imidazolin forms are present in the ratio of 1:1.

Highlights

ONE-POT SYNTHESIS OF THE SUBSTITUTED IMIDAZOLIDIN-2-ONES WITH PARTICIPATION OF THIO BARBITURIC ACID, UREAS AND ARYLGLYOXALS N.M.Коlos, L.L.Zamigaylo, N.V.Chechina Key words: imidozoline-2-ones; one-pot synthesis; tautomerism; thiobarbituric acid; arylglyoxals; ureas Derivatives of imidozoline-2-ones containing the pyrimidinthionic moiety in position 4 have been synthesized by three-component one-pot condensation of thiobarbituric acid, arylglyoxal hydrates and ureas
It has been found that these compounds exist in the solution of DMSO-d6 as a mixture of two tautomeric forms: for products obtained from N-substituted ureas the imidazolidin form predominates; and in the case of urea the imidazolidin and imidazolin forms are present in the ratio of 1:1
Що в конденсаціях за участю димедону або 4-гідроксикумарину, гідратів арилгліоксалів і сечовин були одержані виключно імідазол-2-они, що зумовлено існуванням відповідних β-дикарбонільних сполук переважно в єнольній формі

Summary

Introduction

ONE-POT SYNTHESIS OF THE SUBSTITUTED IMIDAZOLIDIN-2-ONES WITH PARTICIPATION OF THIO BARBITURIC ACID, UREAS AND ARYLGLYOXALS N.M.Коlos, L.L.Zamigaylo, N.V.Chechina Key words: imidozoline-2-ones; one-pot synthesis; tautomerism; thiobarbituric acid; arylglyoxals; ureas Derivatives of imidozoline-2-ones containing the pyrimidinthionic moiety in position 4 have been synthesized by three-component one-pot condensation of thiobarbituric acid, arylglyoxal hydrates and ureas. Встановлено, що отримані сполуки існують у розчині ДМСО-d6 як суміш двох таутомерних форм: для продуктів, одержаних на основі N-заміщених сечовин, переважає імідазолідинова форма, тоді як у випадку сечовини імідазолідинова та імідазолінова форми присутні у співвідношенні 1:1.

Results

Conclusion