New scaffolds for combinatorial synthesis. 1. 5-sulfamoylisatins and their reactions with 1,2-diamines |
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Authors: | Ivachtchenko Alexandre V Il'yin Alexey P Kobak Vladimir V Zolotarev Denis A Boksha Larisa V Trifilenkov Andrey S Ugoleva Dina M |
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Affiliation: | Chemical Diversity Labs, Inc., 11575 Sorrento Valley Road, Suite 211, San Diego, CA 92121, USA. |
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Abstract: | 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. |
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