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Gold‐Catalyzed Post‐Ugi Cascade Transformation for the Synthesis of 2‐Pyridones
Author(s) -
Du Xiaochen,
Yu Jiafeng,
Gong Jing,
Zaman Manzoor,
Pereshivko Olga P.,
Peshkov Vsevolod A.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900027
Subject(s) - chemistry , isocyanide , furan , catalysis , cascade , ring (chemistry) , alkyne , cleavage (geology) , combinatorial chemistry , bond cleavage , stereochemistry , brønsted–lowry acid–base theory , ugi reaction , transformation (genetics) , double bond , organic chemistry , biochemistry , geotechnical engineering , chromatography , fracture (geology) , engineering , gene
A gold‐catalyzed post‐Ugi cascade transformation for the synthesis of 2‐pyridones is described. The process involves furan–alkyne cyclization followed by furan ring‐opening and cleavage of the isocyanide‐originated fragment. The initially formed cis double bond can isomerize into a more stable trans double bond upon prolonged exposure to a strong Brønsted acid. Thus, the overall strategy provides a viable access towards two types of 2‐pyridones.