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Assembly of a 1 H ‐Pyrrol‐2(5 H )‐one Core through a Cascade Ugi Reaction/5‐ endo ‐ dig Carbocyclization/Retro‐Claisen Fragmentation Process
Author(s) -
Peshkov Anatoly A.,
Peshkov Vsevolod A.,
Li Zhenghua,
Pereshivko Olga P.,
Van der Eycken Erik V.
Publication year - 2014
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.201402723
Subject(s) - chemistry , dig , fragmentation (computing) , aldehyde , phenylglyoxal , pyrrole , ugi reaction , cascade , combinatorial chemistry , stereochemistry , organic chemistry , isocyanide , catalysis , operating system , chromatography , amino acid , biochemistry , computer security , arginine , computer science
A cascade transformation involving the Ugi reaction followed by 5‐ endo ‐ dig carbocyclization and retro‐Claisen fragmentation providing access to a 1 H ‐pyrrol‐2(5 H )‐one core is described. The operating protocol is very similar to the typical Ugi reaction settings, while the overall outcome results from the application of a 3‐substituted propiolic acid and a phenylglyoxal as acid and aldehyde components, respectively. The utility of process is demonstrated through the synthesis of a small library of 5‐oxo‐2,5‐dihydro‐1 H ‐pyrrole‐2‐carboxamides.