Synthesis and some reactions of 2-(3,5-dioxo-4-azatricyclo[5.2.2.02,6]undec-8-ene-4-yl)propanoic acid

Abstract

Novel 2-(3,5-dioxo-4-azatricyclo[5.2.2.0 2,6 ]undec-8-ene-4-yl)propanoic acid was synthesized from easily accessible starting material, 4-oxatricyclo[5.2.2.0 2,6 ]undec-8-ene-3,5-dione. Chemical reactivity of the title was investigated. In particular, it was converted into the corresponding acyl chloride and simple amides. Curtius rearrangement of the acyl azide delivered an isocyanate, which was then transformed into a series of polycyclic ureas. Noteworthy, the thermal rearrangement of the azide underwent without interference from the strained double bond present in the parent compound.