Tetramido derivatives of glyoxal

Gilbert, Everett E.

doi:10.1021/je60061a003

Cited by 6 publications

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“…Synthesis of imidazolidines through the cyclocondensation of diamines, bisamides and urea derivatives with aqueous glyoxal and other appropriate carbonyl compounds has been the subject of numerous investigations [1][2][3][4][5][6][7][8][9][10]. In 1962, Slezak et al reported the acid-catalyzed reaction of urea derivatives with aqueous glyoxal leading to the formation of the corresponding glycolurils 1 (Figure 1) [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Unsymmetrical 4,5-Dihydroxy-2-imidazolidinones. Dynamic NMR Spectroscopic Study of the Prototropic Tautomerism in 1-(2-Benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone

2006

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Abstract:The acid-catalyzed cyclocondensation in refluxing acetonitrile of aqueous glyoxal with N-heteroaryl-N'-phenylureas 4a-f (heteroaryl = 2-thiazolyl, 2-pyrimidinyl, 2-pyrazinyl, 2-pyridinyl, 3-pyridinyl and 2-benzimidazolyl) led to the formation of the corresponding 1-heteroaryl-3-phenyl-4,5-dihydroxy-2-imidazolidinones 5a-f. All the products were characterized by elemental and spectroscopic analyses. The free-energy barrier (∆GPfor prototropic tautomerism in 1-(2-benzimidazolyl)-3-phenyl-4,5-dihydroxy-2-imidazolidinone (5f) was determined by dynamic NMR studies to be 81 ± 2 KJ molP -1 P.

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