 An approach to libraries based on tricyclic cyclopentabenzofurans and cyclopentaindoles will be reported. Pd-NHC catalyzed cyclopentannulation of diazabicyclic alkenes with ortho-functionalized aryl halides afforded tricyclic cyclopentabenzofurans and cyclopentabenzoindoles. In all the reactions, a single diastereomer of the cyclopentannulated product is observed. That reaction was found to proceed under both conventional and mircowave heating. Treatment of the cyclopentabenzofurans with methyl bromoacetate/Cs2CO3/MeCN at 50�C generated the alkylated product, which by heating at 80�C resulted in N-N bond cleavage and the corresponding carbamates. These intermediates are deversified by conversion to amides, or by Suzuki reaction to generate the corresponding arylated species.

Synthesis of tricyclic benzofurans/indole ring systems

247th National Meeting (2014)

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