Methyl 12-Methyl-3,9-dinitro-5,6,7,12-tetrahydro-13-oxodibenzo[<i>b</i>.<i>g</i>]bicyclo[3.3.1]nonane-6-carboxylate and Related Compounds

Abstract

A synthesis of the title compound and related structures is reported. The procedure involves double alkylation of a β-ketoester followed by double SNAr ring closure from the γ carbon to give a dibenzo[3.3.1]bicyclic unit. This paper appears to be the first to generate a mid-sized bicyclic target by a double SNAr process. The synthesis can be performed in one step, but yields are superior (52–62%) when a two-stage procedure is used.

Keywords

• double alkylation
• double S_NAr ring closure
• dibenzo[3.3.1]bicyclic systems