Cyclobutane Ring Opening Reactions of 1,2,2a,8b-Tetrahydrocyclobuta[c]-quinolin-3(4H)-ones

Abstract

Two pathways are presented, which allow for the selective cleavage of the C1/C8b bond in the title compounds. The first reaction was found by serendipity when reductive debenzylation was attempted on a heteroanellated azabicyclo[4.2.0]octane. It yielded an eight-membered lactam ring (azocane). The second transformation relies on a rationally designed 1,2-rearrangement reaction, which was introduced because attempts to induce classical Wagner-Meerwein-type 1,2-shifts did not meet with success. The reaction, a retro-benzilic acid rearrangement, allowed for the conversion of a heteroanellated hydroxycyclobutanecarboxylate into the respective cyclopentadione (76% yield).

Key words

metal reductions - lactams - photochemistry - cyclobutanes - rearrangements - fragmentations

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Preliminary communication: Selig, P.; Bach, T. Angew. Chem. Int. Ed. 2008, 47, in press.