Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XV. Synthesis, structure, and reactions with alcohols of N-carbamoyl-1,4-benzoquinone imines

• Published in: Russian journal of organic chemistry Vol. 51; no. 12; pp. 1739 - 1744
• Main Authors: Konovalova, S. A., Avdeenko, A. P., Polishchuk, M. V., Lysenko, E. N., Baumer, V. N., Omel’chenko, I. V., Goncharova, S. A.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-12-2015
• Subjects: Chemistry; Chemistry and Materials Science; Organic Chemistry; Dimethylphenyl; Natural Bond Orbital; Steric Strain; Quinoid Ring; Quinone Imine
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428015120131

The reaction of 4-aminophenols with
N
-nitrourea or with sodium cyanate in acetic acid gave the corresponding 4-ureidophenols which were oxidized to
N
-carbamoyl-1,4-benzoquinone imines, substituted
N
-(4-oxocyclohexa-2,5-dien-1-ylidene)ureas.
N
-(2,6-Dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)urea possessing activated sterically strained C=N bond reacted with alcohols to afford
N
-(1-alkoxy-2,6-dimethyl-4-oxocyclohexa-2,5-dienyl)ureas.