A novel multicomponent reaction involving isoquinoline, allenoate and activated ketone

The reaction of isoquinoline and allenoate with activated ketone resulted in a novel three component reaction, affording [1,3]oxazino[2,3-a]isoquinoline derivatives in moderate yields along with moderate diastereoselectivities via 1,4-dipolar cycloaddition. It was also found that when isatins were used as substrates, the regioselectivity of cycloadducts was different from those using ethyl trifluoropyruvate as substrate.

1,4-Dipole, generated in situ from isoquinoline with allenoate, reacts with activated ketone to afford [1,3]oxazino[2,3-a]isoquinoline derivatives in moderate yields along with moderate diastereoselectivities. This reaction enriches the chemistry of zwitterion formed from nitrogen nucleophile and electron-deficient alkyne.Figure optionsDownload as PowerPoint slide