Just out is a new recipe for ynimines from the corresponding free imines.
Org. Lett. ASAP (DOI: 10.1021/ol2032152)
Having worked quite a lot with imines, I am familiar with how tricky conversions of this type can be. OK, ynimines are probably not the hottest targets for any application, but if you picture these as building blocks – woohoo!
Potential applications are merely hinted upon in this first communication. The authors describe one interesting reaction/rearrangement happening with methyl lithium. (Me like the proposed mechanism from 13 to 24.)
I would love throwing other nucleophiles at it. And electrophiles. Perhaps in combination. And why not some good old Diels-Alder type chemistry? Or photochemistry. If I led a research group remotely connected to heterocyclic chemistry, I would have one guy make one of the ynimines and just spend a year or two seeing how it reacted with different stuff. I have a hunch that would lead to many new fascinating discoveries.
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