Synthesis and Reaction of 3-Aminotropone

Abstract

The synthesis of 3-aminotropone (III) which is one of the fundamental troponoid series aromatic compounds and has not never been synthesized was carried out, and optimal conditions of the ammonolysis of 3-tosyloxytropone (II) were taken in the following ; solvent, isopropanol ; reaction temperature, 45-50° ; reaction time, about 80 min. It was found that bromination of III afforded 3-amino-2-bromotropone (IV) or known 2-bromo-3-hydroxytropone (V), depending on the conditions. The structure of IV was elucidated from a comparison of the NMR spectra of III and IV. Treatment of III with dimethyl sulfate gave 3-methoxytroponeimine (VI), which was isolated as picrate (VII). N-Acetyl derivative (VIII) of III was given by heating of III with acetic anhydride.