Synthesis of 3-Hydroxy-9<i>H</i>-fluorene-2-carboxylates via Michael Reaction, Robinson Annulation, and Aromatization

Abstract

A series of 3-hydroxy-fluorene-2-carboxylate compounds were prepared from Michael addition of acetoacetate to 2-benzylideneindan-l-one followed by Robinson annulation and aromatization. In this reaction, we were able to isolate two Robinson annulation products and characterize them. This sequential reaction could proceed without the isolation of intermediates to give the desired products directly in reasonable yields.

Keywords

• fluorene
• Michael reaction
• Robinson annulation
• oxidation