1-Cyclohexyl-2-cyclohexylamino-5(4H)-imidazolone

Synthesis and Mechanistic Study of Cyclic Oxoguanidines via Zn(OTf)2‐Catalyzed Guanylation/Amidation from Readily Available Amino Acid Esters and Carbodiimides

“…86.6–87.6 °C; 1 H NMR (400 MHz , CDCl 3 , TMS): δ =1.17–1.42 (m, 8 H; CH 2 ), 1.62–1.75 (m, 6 H; CH 2 ), 1.85–2.05 (m, 6 H; CH 2 ), 3.69 (br s, 1 H; CH), 3.95 (s, 2 H; CH 2 ), 4.10 ppm (br s, 1 H; CH); 13 C NMR (100 MHz , CDCl 3 , TMS): δ =24.72, 25.05, 25.56, 25.93, 30.25, 33.31, 50.33, 52.05, 56.19, 155.64, 180.28 ppm; IR (film): $\tilde \nu $ =3326 (NH), 1620 cm −1 (CO); HRMS: m / z calcd for C 15 H 26 N 3 O [ M +H] + : 264.2076; found: 264.2067. The single‐crystal structure 2 c was consistent with that reported 14…”

“…When R 1 and R 2 in the carbodiimides are alkyl groups, 2‐aminoimidazolones 2 a – d , in which the CN double bond is within the five‐membered ring, were exclusively observed. The solid‐state structure of 2 c has been confirmed by previous work 14. In contrast, when R 2 in the carbodiimides are aryl groups, 2‐iminoimidazolidin‐4‐ones 3 a – d were exclusively obtained as an isomer of 2‐aminoimidazolones.…”