Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides

Synthesis of polysubstituted fused pyrroles by gold-catalyzed cycloisomerization/1,2-sulfonyl migration of yndiamides

Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolera...

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Bibliographic Details
Main Authors: Smith, PJ, Jiang, Y, Tong, Z, Pickford, HD, Christensen, KE, Nugent, J, Anderson, EA
Format: Journal article
Language:English
Published: American Chemical Society 2021
Description
Summary:Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.

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