Synthesis of pyrroles by consecutive multicomponent reaction/[4 + 1] cycloaddition of alpha-iminonitriles with isocyanides.

Patrice Fontaine (1) , Géraldine Masson (1) , Jieping Zhu (1)

1 ICSN - Institut de Chimie des Substances Naturelles

[4 + 1] Cycloaddition of alpha,beta-unsaturated imidoyl cyanide (2-cyano-1-azadienes) with isocyanides in the presence of a catalytic amount of AlCl(3) 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.

Domaines: Biologie cellulaire

Patrice Fontaine, Géraldine Masson, Jieping Zhu. Synthesis of pyrroles by consecutive multicomponent reaction/[4 + 1] cycloaddition of alpha-iminonitriles with isocyanides.. Organic Letters, 2009, 11 (7), pp.1555-8. ⟨10.1021/ol9001619⟩. ⟨hal-00385003⟩