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

Ludmila A. Oparina; Anastasiya G. Mal’kina; Nikita A. Kolyvanov; Igor A. Ushakov; Ivan V. Saliy; Konstantin A. Apartsin; Boris A. Trofimov

doi:10.1055/a-1742-2736

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(11): 2635-2646
DOI: 10.1055/a-1742-2736

paper

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

Ludmila A. Oparina

^aA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Anastasiya G. Mal’kina

^aA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Nikita A. Kolyvanov

^aA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Igor A. Ushakov

^aA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Ivan V. Saliy

^aA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

,

Konstantin A. Apartsin

^bBiomedical Research and Technology Department of the Irkutsk Scientific Center, Siberian Branch, Russian Academy of Sciences, 134 Lermontov Str., 664033 Irkutsk, Russian Federation

,

Boris A. Trofimov∗

^aA.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation

› Institutsangaben

Abstract

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Abstract

The ring-opening/functionalization of 1-pyrrolines by cyanoacetylenes or acetylenic ketones (20–80 °C, MeCN, H₂O) 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.

Key words

cleavage reactions - electrophilic acetylenes - multicomponent reactions - 1-pyrrolines - zwitterions

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Referenzen

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