Amide-Glyoxal Reaction Products¹

Synthesis of α‐Substituted Succinimides from Glyoxal and Ketene N,S‐Acetals

“…Glyoxal usually acted as the dinucleophilic reagents to form two identical bonds meanwhile . For example, reaction with ureas gave 4,5‐dihydroxyimidazolidin‐2‐ones (Scheme , eq 1) and reaction with diketosulfide provided thiophene‐2,5‐dicarbonyl compounds (Scheme , eq 2) . In 2003, Guillaumet's group reported the reaction of 40% aqueous glyoxal with triazine derivatives to allow the formation of two C−N bonds to give C(6)‐functionalized dihydroimidazotriazines (Scheme , eq 3) .…”

Evidences of some unusual behaviours of 2‐aminothiazol and 2‐aminobenzothiazol in reactions with formaldehyde and glyoxal

“…Reaction of amines (RNH 2 ) and amides (RCONH 2 ) with glyoxal and formaldehyde gives a wide variety of products depending upon the nature of R and, in certain cases, upon the reaction conditions [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. In 1967, Currie and co-workers reported the base-catalyzed reaction of formamide or methane sulphonamide with glyoxal leading to the corresponding 2,3,5,6-tetrahydroxypiperazines (1) [6][7].…”

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

“…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].…”