Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides

Autor:	Edward A. Anderson, Kirsten E. Christensen, Zixuan Tong, Helena D. Pickford, Yubo Jiang, Jeremy Nugent, Philip J. Smith
Rok vydání:	2021
Předmět:	Sulfonyl chemistry.chemical_classification chemistry.chemical_compound Cycloisomerization chemistry Organic Chemistry Functional group Physical and Theoretical Chemistry Biochemistry Combinatorial chemistry Catalysis Pyrrole
Zdroj:	Organic Letters. 23:6547-6552
ISSN:	1523-7052 1523-7060
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0e914b5ef7c51ba2da2d1bf8ec849db6 https://doi.org/10.1021/acs.orglett.1c02360 Zobrazit plný text záznamu