Disubstituted malononitrile derivatives have been found to be useful intermediates and/or targets for creation of numerous pharmaceutical chemicals as well as crop and animal protection products.  To this extent, our lab has recently developed novel one-step and one-pot syntheses for the reductive alkylation of malononitrile to  efficiently prepare a large scope of monosubstituted malononitriles.   Once a monosubstituted derivative has been prepared, simple alkylation techniques can be employed to create useful disubstituted malononitrile derivatives.  Further reaction of disubstituted malononitriles containing phenol derivatives allows for O-alkylation and pyridine derivatives allows for N-alkylation. The disubstituted malononitriles, specifically designed to include alkene or alkyne functional groups, react with nitrile oxides to prepare isoxazolines and isoxazoles, respectively. This paper will also discuss the scope and limitations of this cycloaddition reaction.

Synthesis of isoxazole and isoxazoline containing malononitrile derivatives

239th National Meeting (2010)

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