Piperazine as Leaving Group in A3 Adducts: Fast Access to Alkynyl Indoles

Mansour Dole Kerim (1, 2) , Laurent El Kaim (1, 2)

1 DCSO - Laboratoire de synthèse organique
2 ENSTA Paris - École Nationale Supérieure de Techniques Avancées

The A3 coupling between N-ethylpiperazine and electron-rich aromatic aldehydes forms adducts that may be easily used as electrophiles towards electron-rich heterocycles such as indoles. The removal of the piperazine moiety is triggered by the addition of 1,2-dibromoethane. Overall, the reaction provides efficient access to alkynyl indoles and pyrroles.

Domaines: Chimie organique

Mansour Dole Kerim, Laurent El Kaim. Piperazine as Leaving Group in A3 Adducts: Fast Access to Alkynyl Indoles. SYNLETT, 2016, 27 (10), pp.1572-1576 ⟨10.1055/s-0035-1561396⟩. ⟨hal-01444342⟩