- Novel one-pot cyclization of ortho substituted benzonitriles to 3-amino-1,2-benzisoxazoles
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A novel one-pot synthesis of 3-amino-1,2-benzisoxazoles (iii), from ortho substituted benzonitriles (i), is described. The synthesis likely involves a SNAr reaction of an activated ortho halo or nitro group by a hydroxamate anion, followed by an intra-mol
- Palermo
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- Studies on the synthetic compatibility of aryloxime linkers in the solid-phase synthesis of 3-aminobenzisoxazoles
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Further exploration of the scope of our solid-phase method for the synthesis of 3-aminobenzisoxazoles (using the Kaiser oxime resin 1) is described. The effects of base, leaving group, and solvent on the nucleophilic aromatic substitution based resin-loading reaction are discussed. Representative aryloxime intermediates were subjected to a variety of acidic conditions commonly used in protecting group removal to establish the acid stability profile of this linker. Regioselectivity was evaluated with various di- and trifluorobenzonitriles, which gave single benzisoxazole products after loading and cyclorelease reactions. Substituent effects observed in the course of the acid stability and regioselectivity studies suggest that the nitrile plays a critical role in the oxime hydrolysis mechanism. Finally, to establish the compatibility of the aryloxime linker with a variety of useful on-resin synthetic transformations, functionalized substrates were loaded onto resin 1, and carbon-nitrogen, carbon-oxygen, and carbon-carbon bond-forming reactions were successfully executed.
- Lepore, Salvatore D.,Wiley, Michael R.
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p. 2924 - 2932
(2007/10/03)
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