2-{[Tris(hydroxymethyl)methyl]amino (2H)-One and Its 6-Hydroxy and 6-Methoxy Derivatives

Abstract

The title compounds, 2-{[tris(hydroxymethyl)methyl]amino-methylene}cyclohexa-3,5-dien-1(2H)-one, C<inf>11</inf>H<inf>15</inf>NO<inf>4</inf>, (I), 6-hydroxy-2-{[tris(hydroxymethyl)methyl]aminomethylene}-cyclohexa-3,5-dien-1(2H) -one, C<inf>11</inf>H<inf>15</inf>NO<inf>5</inf> (II), and 6-methoxy-2-{[tris(hydroxymethyl)methyl]aminomethylene}cyclo-hexa-3,5-dien-1(2H) -one, C<inf>12</inf>H<inf>17</inf>NO<inf>5</inf>, (III), adopt the ketoamine tautomeric form, with the formal hydroxy H atom located on the N atom, and the NH group and oxo O atom display a strong intramolecular N-H⋯O hydrogen bond. The N-H⋯O hydrogen-bonded rings are almost planar and coupled with the cyclohexadiene rings. The carbonyl O atoms accept two other H atoms from the alcohol groups and one from the phenol group in (II), but from only one alcohol H atom in (III).