Compared with the well-developed cyclization of functionalized propargylamines, the use of unactivated tertiary propargylamines to access pyrroles remains challenging. Herein, we report an efficient method for constructing tetrasubstituted pyrroles via a DBU-mediated intramolecular cycloaddition of -alkyl propargylamines. This reaction employs cyclization to access dihydropyrrole intermediates, followed by oxidation to produce pyrroles in the presence of 2,3-dichloro-5,6-dicyano--benzoquinone. In addition, a broad substrate scope, high atom economy, high selectivity, and simple operation are also advantages of this protocol.

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http://dx.doi.org/10.1021/acs.joc.4c02198DOI Listing

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