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

Mol Divers. 2021 Nov;25(4):2441-2446. doi: 10.1007/s11030-020-10146-7. Epub 2020 Oct 10.

Abstract

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.

Keywords: Domino reaction; Nitriles; Nitroalkenes; Pyrroloisoquinolines; Unsaturated ketones.

MeSH terms

  • Ketones*

Substances

  • Ketones