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The reaction of 2-aminomethylaniline with 1,3-dicarbonyl compounds gives a series of 1,2,3,4-tetrahydroquinazoline derivatives. A ring-chain tautomeric equilibrium of the type enamine-1,2,3,4-tetrahydroquinazoline is observed in solutions of these compounds and its position depends of the structure of the starting dicarbonyl component and the solvent polarity.
In this work 32 1,2,3,4-tetrahydroquinazoline derivatives were synthesized by the reaction of 2-aminomethylaniline with aldehydes and ketones and their ring-chain tautomerism studied by 1 H, 13 C and 15 N NMR spectroscopy. The ketone, as well as the alkyl aldehyde, derivatives were found to favor exclusively ring forms, whereas tautomeric equilibria were observed...
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