One-pot O-to-C atom swap converts isoxazoles into valuable pyrrole scaffolds
Scientists introduced a single-step O-to-C atom replacement that turns isoxazoles into pyrroles, using an N-propargylic enaminone as a key intermediate.
A novel synthetic route has been reported that converts isoxazoles into pyrroles via an O-to-C skeletal edit performed in a single reaction vessel. The study identified N-propargylic enaminones as a pivotal intermediate, offering a retrosynthetic disconnection not available through conventional methods. This approach allows regioselective construction of challenging pyrrole architectures, expanding options for heterocyclic drug development.
While optimizing the sequence, the team observed unanticipated reactivity of the enaminone and created a predictive computational model to explain the conformational influences on outcome. All crystallographic data have been deposited with the Cambridge Crystallographic Data Centre, and full experimental details are provided in the supplementary information. Funding was supplied by the NIH, NSF GRFP, and the Beckman Scholars Program.
Why it matters
The method gives chemists a faster, more versatile way to build pyrrole rings that are common in medicines.
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