Organic Chemistry

Iron Catalyzed Formal [3+2] Cycloaddition of Tetrahydroisoquinoline Affording Amide-bearing Dihydropyrrolo[2,1-a]isoquinolines

Abstract

We have developed an iron(III) chloride hexahydrate catalyzed formal [3+2] cycloaddition of tetrahydroisoquinolines with amide group-bearing Morita-Baylis-Hillman (MBH) carbonates. A range of highly functionalized dihydropyrrolo[2,1-a]isoquinolines could be prepared through SN2’/oxidation/ electrocyclization/aromatization cascade (32-62% yield).


Content

Thumbnail image of Chemrxiv--20200321--FeCl3--3plus2--3.pdf

Supplementary material

Thumbnail image of 191118CHL_0m.txt
191118CHL 0m