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
Peshkov A.A. Bakulina O. Darin D. Kantin G. Bannykh A. Peshkov V.A. Krasavin M.
19 March 2021John Wiley and Sons Inc
European Journal of Organic Chemistry
2021#2021Issue 111726 - 1731 pp.
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.
Ammonium acetate , Aromatization , Castagnoli-Cushman reaction , Decarboxylation , Double bond isomerization
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Department of Natural Products Chemistry, Institute of Chemistry, Saint Petersburg State University, 26 Universitetskyi prospekt, Peterhof, 198504, Russian Federation
Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, Nur-Sultan, 010000, Kazakhstan
Immanuel Kant Baltic Federal University, Kaliningrad, 236041, Russian Federation
Department of Chemistry, University of Jyväskylä, Survontie 9B, Jyväskylä, 40014, Finland
Department of Natural Products Chemistry
Department of Chemistry
Immanuel Kant Baltic Federal University
Department of Chemistry
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