Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters

Abstract DBN (1,5-diazabicyclo[4.3.0]non-5-ene) and DBU (1,8-diaza­bicyclo[5.4.0]undec-7-ene) react with methyl esters of acetylenic acids and excess water (the reactant molar ratio 1:1, in aqueous MeCN, at 20–25 °C, for 48 h) to afford acetylenic amides with pyrrolidone and caprolactam moieties in...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2018-02, Vol.50 (4), p.853-858
Main Authors: Shemyakina, Olesya A., Volostnykh, Olga G., Stepanov, Anton V., Mal’kina, Anastasiya G., Ushakov, Igor A., Trofimov, Boris A.
Format: Article
Language:English
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Summary:Abstract DBN (1,5-diazabicyclo[4.3.0]non-5-ene) and DBU (1,8-diaza­bicyclo[5.4.0]undec-7-ene) react with methyl esters of acetylenic acids and excess water (the reactant molar ratio 1:1, in aqueous MeCN, at 20–25 °C, for 48 h) to afford acetylenic amides with pyrrolidone and caprolactam moieties in 89–100% yields. The synthesis involves amines formed in situ from the cyclic amidines, which further react with acetylenic esters.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1591852