Pseudo-Multicomponent Reactions of Arynes with N-Aryl Imines

Juan-Carlos Castillo (1) , Jairo Quiroga (2) , Rodrigo Abonia (2) , Jean Rodriguez (1) , Yoann Coquerel (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 Departamento de Química

Pseudo-three-component reactions are de- scribed for the conversion of simple N-aryl imines into 1,2- dihydroisoquinoline-type products. The approach relies on a regioselective cascade reaction involving two equivalents of the aryne component iteratively as a dienophile and as an electrophile. Some examples of related, more complex pseudo-four-component cascade processes are also reported.

Keywords: arynes; cycloaddition; heterocycles; dihydroisoquinolines; multicomponent reaction

Domains: Organic chemistry

Juan-Carlos Castillo, Jairo Quiroga, Rodrigo Abonia, Jean Rodriguez, Yoann Coquerel. Pseudo-Multicomponent Reactions of Arynes with N-Aryl Imines. Journal of Organic Chemistry, 2015, 80, pp.9767. ⟨10.1021/acs.joc.5b01564⟩. ⟨hal-01224324⟩