New scaffolds for combinatorial synthesis. 1. 5-sulfamoylisatins and their reactions with 1,2-diamines.

3,3-Dichloro-5-(4-methylpiperidinosulfonyl)-2-indolinone (3) and 5-sulfamoylisatins 4 have been synthesized from 5-chlorosulfonyl-3,3-dichloro-2-indolinone (1). Compounds 4 are promising scaffolds for the solid- and liquid-phase syntheses of new combinatorial libraries of various heterocycles. Thus, the reactions of 4 with 1,2-diamines, such as o-phenylenediamine (5) and aminoguanidine hydrochloride (6), 1,2-diaminoimidazoles (9), and thiosemicarbazide led, respectively, to new heterocycles 7 and 8 and new combinatorial libraries of triazinoindoles 10 and 15. Chemsets 4, 10, and 15 were isolated as crystalline solids that were purified by recrystallization from a suitable solvent and characterized by spectroscopic methods.