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Three‐Component Castagnoli‐Cushman Reaction of 3‐Arylglutaconic Acid Anhydrides, Carbonyl Compounds, and Ammonium Acetate: a Quick and Flexible Way to Assemble Polysubstituted NH ‐δ‐lactams
Author(s) -
Peshkov Anatoly A.,
Bakulina Olga,
Dar'in Dmitry,
Kantin Grigory,
Bannykh Anton,
Peshkov Vsevolod A.,
Krasavin Mikhail
Publication year - 2021
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.202001617
Subject(s) - chemistry , isomerization , ammonium acetate , component (thermodynamics) , organic chemistry , ammonium , combinatorial chemistry , catalysis , physics , high performance liquid chromatography , thermodynamics
A practical straightforward synthesis of medicinally important NH ‐δ‐lactams through the three‐component Castagnoli‐Cushman reaction of 3‐arylglutaconic anhydrides with carbonyl compound and ammonium acetate has been developed. The scope of the protocol has been thoroughly explored paying particular attention to the carbonyl component using wide array of aliphatic and aromatic aldehydes as well as rarely involved cyclic and acyclic ketones. Synthetic potential of prepared compounds was demonstrated by a series of post‐modifications, including unexpected isomerization.