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Synthesis 2022; 54(11): 2635-2646
DOI: 10.1055/a-1742-2736
DOI: 10.1055/a-1742-2736
paper
δ-Keto Aminoacrylonitriles and δ-Keto Aminoenones from 1-Pyrrolines, Cyanoacetylenes, and Acetylenic Ketones
This 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).
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 - zwitterionsSupporting 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
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