Fontaine, PatriceMasson, GeraldineZhu, Jieping2010-11-252010-11-252010-11-25200910.1021/ol9001619https://infoscience.epfl.ch/handle/20.500.14299/58396[4 + 1] Cycloaddn. of alpha ,beta -unsatd. imidoyl cyanide (2-cyano-1-azadienes) with isocyanides in the presence of a catalytic amt. of AlCl3 afforded polysubstituted 2-amino-5-cyanopyrroles in good to excellent yields. In combination with the IBX/TBAB-mediated oxidative Strecker reaction, this important heterocycle is readily synthesized in two steps from simple starting materials. [on SciFinder (R)]Cycloaddition reaction; Cycloaddition reaction catalysts ([4+1]; prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Nitriles Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (imino; prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Amines Role: RCT (Reactant)RACT (Reactant or reagent) (multicomponent oxidative Strecker reaction of alphabeta -unsatd. aldehydesaminesand trimethylsilyl cyanide in presence of IBX and TBAB); Strecker amino acid synthesis (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Isocyanides Role: RCT (Reactant)RACT (Reactant or reagent) (prepn. of 2-amino-5-cyanopyrroles by consecutive multicomponent oxidative Strecker reaction/[4 + 1] cycloaddn. of alpha -iminonitriles with isocyanides in the presence of a catalytic amt. of AlCl3); Aldehydes Role: RCT (Reactant)RACT (Reactant or reagent) (alphabeta -unsatd.; multicomponent oxidative Strecker reaction of alphabeta -unsatd. aldehydesaminesand trimethylsilyl cyanide in presence of IBX and TBAB)aminocyanopyrrole prepn; pyrrole aminocyano prepn; oxidative Strecker reaction cycloaddn imino nitrile isocyanidetext::journal::journal article::research article