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Title: METHOD OF SYNTHESIZING ISOINDOLEQUINONES AND DERIVATIVES THEREOF

Inventor(s): W. Youngs, M. Chakraborty

Disclosure 309 U.S. Patent Notice of Allowance (4/98)

This invention provides a novel method for synthesizing isoindolequinones and derivatives thereof.New and general synthesis of substituted isoindolequinones, also referred to as isoindolediones, from a diethynylhydroquinone and primary amines in virtually quantitative yields have been discovered.

The advantages afforded by this method are (1) use of readily available and synthesizable starting materials, (2)uncatalyzed one-pot conversion or synthesis, (3) ease of chromatographic isolation of the product, (4) reaction generality with respect to primary amines, (5) optional use of catalyst, (6) high yields up to 98% have been observed,(7) moisture insensitivity, (8) use of cost effective and environmentally benign solvents, and (9) a reaction that is both simple and convenient.

Isoindolequinones have been shown to have useful radiosensitization properties, in that they selectively sensitize hypoxic cells in some tumors to the lethal effect of radiation.

This method is ideally suitable for (a) synthesizing isoindolequinones in high yields which are antimicrobials and potential radiosensitizers for cancer therapy, (b)useful as a general synthetic route for differently substituted isoindolequinones, isobenzofuran-quinones and related heterocycles that may have antibiotic activity, and(c) also potentially usable for polymer and dendrimer synthesis.