120 Microwave Assisted SOLID-Supported ORGANIC SYNTHESIS of 2,3-Disubstituted-1,4-Naphthoquinones

Wednesday, November 4, 2009: 11:20 AM
Rio Grande (Camino Real Hotel)
Israel Garcia-Martinez , Departament of Chemistry, University of Texas at El Paso, El Paso, TX
Luis E. Martinez , Department of Chemistry, University of Texas El Paso, El Paso, TX
This research work has been focused on the combinatorial solid phase organic synthesis (SPOS) of different bioactive compounds utilizing transition metal mediated reactions via microwave assisted organic synthesis (MAOS).  We reported a microwave-assisted solid-supported Dötz benzannulation of chromium carbene complexes with various alkynes to afford 2,3-disubstituted-1,4-naphthoquinone derivatives in good to moderate yields with high purities. Improvement of the synthesis of chromium carbene complexes by utilizing the first “catch-release” synthesis of both solid- and non-supported chromium Fischer carbene complexes is presented. Finally, the solid-phase organic synthesis of triazole containing 1,4-naphthoquinone derivatives through solid-supported Dötz benzannulation and Huisgen 1,3-dipolar cycloaddition reaction, followed by the oxidative cleavage of the resulting resin-bound click product is reported.
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