Synthesis of 2-(4-azulenyl)ethanamine derivatives as a nonbenzenoid analog of biogenic amine

Article abstract of DOI:10.1246/bcsj.56.2311

2-(4-Azulenyl)ethanamine derivatives, nonbenzenoid analogs of the biologically active amine, were synthesized by the action of methyleneammonium salts on sodium 4-methylazulenide, sodium 4,6,8-trimethylazulenide, and sodium guaiazulenide. These compounds, as well as their hydrochlorides, were characterized by UV, IR, **1H NMR, **1**3C NMR, and MS data. The reaction of sodium guaiazulenide and N-ethylidenemethylamine also yielded the corresponding 2-(4-azulenyl)ethanamine derivatives, but the low yield of the product showed that the electrophilicity of azomethine carbon atom to 4-methylene carbanion was insufficient. The enzyme activity for some of those products was investigated. Negligible effect was found on prostaglandin 15-hydroxydehydrogenase, and considerable inhibition to cyclic AMP-phosphodiesterase, in vitro.