Catalysts-Controlled Roles Exchange between 2,3-Diaryl-2H-azirines and Acetone: Chemodivergent Synthesis of Pyrroles and 3-Oxazolines

Abstract

We report two practical and step-economical methodologies for the chemodivergent synthesis of tri-substituted pyrroles and 3-oxazolines from the domino reactions of 2H-azirines and acetone. For instance, acetone served as a nucleophile to react with 2H-azirines under the basic conditions to furnish pyrroles. Upon changing the catalyst to TfOH, acetone served as an electrophile to synthesize 3-oxazolines. Moreover, the products could be synthesized on a gram scale, and the possible catalytic cycles were proposed.

[3 + 2] Annulation of Vinyl Azides with Aldehydes for the Synthesis of 3-Oxazolines via the [CO + CCN] Strategy

“…Oxazoline, a crucial five-membered heterocyclic compound, exhibits remarkable biological activity due to its unique nitrogen–oxygen backbone structure . This distinctiveness has propelled its widespread and valuable applications across diverse fields such as pharmaceuticals and biology, natural product chemistry, polymer materials, and so forth . Notably, 2-oxazolines hold a prominent status as chiral ligands in asymmetric catalysis, while 4-oxazolines perform pivotal duties in synthesizing cyclic and acyclic compounds .…”