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Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221
Graphical Abstract
Figure 1: Compounds described in the literature containing an aminal core for various applications. The amina...
Scheme 1: Synthetic approaches for the formation of the tetrahydroquinazoline moiety. Dashed lines indicate b...
Scheme 2: Oxidation and reduction reactions of tetrahydroquinazolines. Dashed lines indicate both cyclized or...
Figure 2: Hydrolysis of the aminal core of tetrahydroquinazolines 1 into the corresponding diamines 2 and ald...
Scheme 3: Reagents and conditions: (i) MeI, DIPEA, DMAc, 40 °C, 24 h; (ii) R1-NH2 or MeNH3Cl and Et3N, DMF, 4...
Scheme 4: Reagents and conditions: (a) (i) MeNH3Cl, Et3N, DMF, 70 °C, 3 h; (ii) AcOH, 70 °C, 4 h; (iii) n-PrB...
Figure 3: pH-Stability test of the aminal core toward hydrolysis in dependency of different substitution patt...
Figure 4: Kinetic analysis of hydrolysis of reference compound 8a in dependency of different pH values and ca...
Figure 5: Differences in energy along the reaction coordinate using the functional B3LYP-D3 for the hydrolysi...
Figure 6: Reaction equilibrium between tetrahydroquinazoline 1, the corresponding diamine 2 and aldehyde 3 in...
Figure 7: Minimum energy conformers in their neutral form with (a) an axial orientation of the phenyl system ...