Facile synthesis of pyrrolo[2,1-a]isoquinolines by domino reaction of 1-aroyl-3,4-dihydroisoquinolines with conjugated ketones, nitroalkenes and nitriles

• DOI: 10.1007/s11030-020-10146-7
• Publication Date: 2020-10-10T16:02:52Z
• Authors: Grigorii S. Astakhov; Rinat R. Shigaev; Tatiana N. Borisova; Anastasia A. Ershova; Alexander A. Titov; Alexey V. Varlamov; Leonid G. Voskres...; Maria D. Matveeva
• Keywords: Domino

A convenient protocol for the synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines with various electron-withdrawing substituents at C-2 atom is described. This approach is based on the two-component domino reaction of 1-aroyl-3,4-dihydroisoquinolines with α,β-unsaturated ketones, nitroalkenes and acrylonitrile. Depending on the selected substrates, the reaction was performed in TFE under reflux or under microwave irradiation. Only for the two examples, a transition metal catalyst was used.