Microwave-assisted solid-phase organic synthesis of 1,4-naphthoquinone derivatives

ORGN 26

Shanmugasundaram Muthian, smuthian@utep.edu and Luis E. Martinez, luisem@utep.edu. Department of Chemistry, University of Texas at El Paso, 500 West University Ave, El Paso, TX 79968
The solid-phase organic chemistry offers an efficient route to construct large libraries of small organic molecules for drug discovery. 1,4-Naphthoquinone derivatives display a wide spectrum of biological activities. This presentation involves microwave-assisted solid-phase Dotz benzannulation of 1 with various alkynes, followed by the oxidation of the resulting resin-bound 1,4-naphthols 3. This pathway leads to the biologically important 2,3-disubstiuted-1,4-naphthoquinone derivatives in good to moderate yields. In addition to alkynes, the reaction has been extended to 1,3-diynes.