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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
a   A.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
a   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
,
Nikita A. Kolyvanov
a   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
,
Igor A. Ushakov
a   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
,
Ivan V. Saliy
a   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
,
Konstantin A. Apartsin
b   Biomedical 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∗
a   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation
› Author AffiliationsThis work was carried out with the financial support from the Ministry of Science and Higher Education of the Russian Federation (No. AAAA-A16-116112510005-7).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1742-2736.
  • Supporting Information


Publication History

Received: 09 December 2021

Accepted after revision: 17 January 2022

Accepted Manuscript online:
17 January 2022

Article published online:
07 March 2022

© 2022. Thieme. All rights reserved

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