A common heterocyclic compound, 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, molecular formula is C4H6N4O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 496-46-8.
3a-Methylglycoluril 1 (0.26 g, 1.67 mmol), glycoluril 2 (1.42 g, 10 mmol) and paraformaldehyde (0.9 g, 30 mmol) were added to concentrated hydrochloric acid (5 ml), and the resultant mixture was heated at 95 C for 24 h. After evaporation of the solvent, the residue was added to water (300 ml) and heated under stirring. The white solid was filtered, and then added to a mixed solvent (30 ml) consisting of formic acid and acetic acid in a ratio of 2:1 (v/v). After thorough stirring, the insoluble material (CB[6]) was removed by filtration, and acetone was added to the acidic filtrate. The precipitates generated therein were collected to afford the desired product 4 in a yield of 14%. TOF mass: m/z 1033 (M+Na+). 1H NMR (500 MHz, in D2O with Na2SO4): delta 5.66 (d, Jin,out = 15.8 Hz, 11H, methylene Hout), 5.59 (d, Jin,out = 16 Hz, 1H, methylene Hout), 5.55 (s, 10H, methine H), 5.29 (s, 1H, methine H), 4.35 (d, Jin,out = 16 Hz, 1H, methylene Hin), 4.28 (d, Jin,out = 15.8 Hz, 11H, methylene Hin) and 1.75 ppm (s, 3H, methyl H). 13C NMR (125 MHz, in D2O with Na2SO4): delta 157.7 (C’O), 157.2 (CO), 77.1 (CH), 74.8 (C-CH3), 71.0 (CH), 52.1 (CH2), 48.1 (CH2) and 20.2 ppm (CH3).
The synthetic route of Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione has been constantly updated, and we look forward to future research findings.
Reference:
Article; Ahmed, Mostafa M.; Koga, Kazutaka; Fukudome, Makoto; Sasaki, Hideaki; Yuan, De-Qi; Tetrahedron Letters; vol. 52; 36; (2011); p. 4646 – 4649;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem