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Published on: April 9, 2021
Silver-Catalyzed Regioselective Oxacyclization of 3-Alkynyl Pyrroles: Straightforward Route to 2,3,5-Triarylated
Fatma Cherif1,2,3, Julien Petrignet3, Pierre-Olivier Delaye3
1Laboratoire de Chimie (Bio) Organique Structurale et de Polymères: Synthèse et Etudes Physico-Chimiques (LR99ES14), Département de Chimie, Faculté des Sciences de Tunis, Université de Tunis El Manar I, Tunis 2092, Tunisie.
Abstract:
We present a method for the silver-catalyzed oxacyclization of 3-alkynylpyrroles to create the pyrano[3,4-b]pyrrolone scaffold. This method exhibits high regioselectivity, enabling position-specific functionalization of the pyrrole core without the need for N-protection. It is also compatible with a broad range of substrates. Using this strategy, we synthesized a small library of novel triarylated pyranopyrroles, thereby enabling the creation of substitution patterns that were previously challenging to achieve. This methodology, therefore, provides a versatile approach to heteroaromatic architectures that are potentially relevant in drug discovery and chemical biology.
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