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Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis

Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [Ar C≡CCH=CHC(=O)Ar ], with 3-oxo-3-phenylpropanenitrile (NCCH COPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4-26 h affords polyfunctional δ-diketones as a product of regioselective Mi...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-02, Vol.27 (4), p.1256
Main Authors: Igushkina, Anastasiya V, Golovanov, Alexander A, Vasilyev, Aleksander V
Format: Article
Language:English
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Summary:Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones [Ar C≡CCH=CHC(=O)Ar ], with 3-oxo-3-phenylpropanenitrile (NCCH COPh) in the presence of sodium methoxide MeONa as a base in MeOH at room temperature for 4-26 h affords polyfunctional δ-diketones as a product of regioselective Michael addition to the double carbon-carbon bond of starting enynones. The δ-diketones have been formed as mixtures of two diastereomers in a ratio of 2.5:1 in good general yields of 53-98%. A synthetic potential of the obtained δ-diketones has been demonstrated by heterocyclization with hydrazine into substututed 5,6-dihydro-4 -1,2-diazepine.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27041256