Synthesis of iminonitriles by oxidative three-component Strecker reaction of aldehydes, amines, and TMSCN

February 20, 2024

• Title:       

  Synthesis of iminonitriles by oxidative three-component Strecker reaction of aldehydes, amines, and TMSCN

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  Synthesis of iminonitriles by oxone/tbab-mediated one-pot oxidative three-component strecker reaction

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  Scheme 1

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  In 2008, our group reported a one-pot  oxidative three-component Strecker reaction for the syn-  thesis of α-iminonitriles from aldehydes, amines, and trimethylsilyl cyanide (TMSCN) using o-iodoxybenzoic  acid (IBX) as oxidant assisted by tetra-n-butylammonium bromide (TBAB) (Scheme 1, eq 1).Subsequently,  new syntheses of functionalized amides, indolizidines,  and polysubstituted pyrroles were developed using α-iminonitriles as key intermediates. In our continued efforts aimed at further developing the promising field of α-  iminonitriles, a new user- and eco-friendly protocol with an even broader application scope was proved necessary.  We report herein that the same oxidative multicomponent  reaction can be realized using innocuous Oxone as oxidizing agent in the presence of TBAB (CAS 1643-19-2) and sodium bicarbonate (CAS 144-55-8) in a biphasic solvent system (toluene/H₂O) to  afford the desired α-iminonitriles in good to excellent yields (Scheme 1, eq 2).