Acrylonitrile substructures

An interesting approach to incorporate acrylonitrile substructures into morphinans is the van Leusen homologation reaction in which the standard reagent... 

Schiitz J, Windisch P, Kristeva E, Wurst K, Ongania K-H, Horvath UIE, Schottenberger H, Laus G, Schmidhammer H (2005) Mechanistic diversity of the van Leusen reaction applied to 6-ketomorphinans and synthetic potential of the resulting acrylonitrile substructures. J Org Chem 70 5323-5326... 

Cycloaddition of trimethylsilyldiazomethane with activated olefins leads to pyrazoline derivatives that have the SMA substructure. Two examples are reported in the literature. The first concerns addition to acrylonitrile that gives 5-trimethylsilyl-3-cyano-A2-pyrazoline in good yield.111... 

Greiner E, Schottenberger H, Wurst K, Schmidhammer H (2001) Novel class of morphinans with acrylonitrile incorporated substructures as key intermediates for non-oxygen-bridged opioid ligands. J Am Chem Soc 123 3840-3841... 

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