Science of Synthesis

Menon, R. S.; Nair, V., Science of Synthesis: Multicomponent Reactions, (2014) 1, 527.

Polysubstituted 2-amino-5-cyanopyrroles ‌32‌ can be accessed from aluminum trichloride catalyzed [4 + 1] annulation of 2-cyano-1-azadienes ‌31‌ (α,β-unsaturated imidoyl cyanides) with isocyanides.[‌23‌] Although the [4 + 1] annulation involves only two reaction partners, the azadiene reactant is assembled in a multicomponent reaction, i.e. an oxidative Strecker reaction involving an enal, trimethylsilyl cyanide, and an amine, mediated by 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (IBX)/tetrabutylammonium bromide (‌Scheme 19‌).

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References