δ-Keto Aminoacrylonitriles and δ-Keto Aminoenones from 1-Pyrrolines, Cyanoacetylenes, and Acetylenic Ketones

δ-Keto Aminoacrylonitriles and δ-Keto Aminoenones from 1-Pyrrolines, Cyanoacetylenes, and Acetylenic Ketones

Abstract The ring-opening/functionalization of 1-pyrrolines by cyano­acetylenes or acetylenic ketones (20–80 °C, MeCN, H 2 O) affords δ-keto aminoacrylonitriles and δ-keto aminoenones, mostly as the Z -isomers, in up to 85% yields. The synthesis involves C(2)–N bond cleavage in the intermediate hemi...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Synthesis (Stuttgart) 2022-06, Vol.54 (11), p.2635-2646
Hauptverfasser: Oparina, Ludmila A., Mal’kina, Anastasiya G., Kolyvanov, Nikita A., Ushakov, Igor A., Saliy, Ivan V., Apartsin, Konstantin A., Trofimov, Boris A.
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Abstract The ring-opening/functionalization of 1-pyrrolines by cyano­acetylenes or acetylenic ketones (20–80 °C, MeCN, H 2 O) affords δ-keto aminoacrylonitriles and δ-keto aminoenones, mostly as the Z -isomers, in up to 85% yields. The synthesis involves C(2)–N bond cleavage in the intermediate hemiaminal resulting from the intermediate 1,3(4)-dipolar 1-pyrroline/acetylene complexes and water.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1742-2736