Substrate-controlled chemoselective synthesis of 1-sulfonylquinazoline-2,4(1H,3H)-diones and 2-sulfonamidobenzonitriles

We have developed a diversity-oriented, substrate-controlled, chemoselective synthetic method for a variety of structurally diverse 1-sulfonylquinazoline-2,4(1H,3H)-diones and 2-sulfonamidobenzonitriles. This substrate-controlled synthesis is accomplished through the condensation reaction of 2-(sulfonamido)benzamides with or without an N-methyl group on the amides. The reactions are fulfilled within half an hour at room temperature with solid triphosgene as a convenient condensing agent and pyridine as an acid acceptor. This protocol features easily available starting materials, mild reaction conditions, easy experimental operation, and moderate to excellent yields of products.