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Synthesis of Acetylenic Amides with Propyllactam Moieties by In Situ DBU or DBN Ring-Opening Rearrangement in the Presence of Acetylenic Esters
Synthesis ( IF 2.6 ) Pub Date : 2017-12-07 , DOI: 10.1055/s-0036-1591852
Boris Trofimov , Olesya Shemyakina , Olga Volostnykh , Anton Stepanov , Anastasiya Mal’kina , Igor Ushakov

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.

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.



中文翻译:

在乙炔酯存在下原位DBU或DBN开环重排合成含丙基内酰胺的乙酰胺。

摘要

DBN(1,5-二氮杂双环[4.3.0] non-5-ene)和DBU(1,8-二氮杂双环[5.4.0]十一烷基-7-ene)与炔酸的甲酯和过量的水(反应物)反应摩尔比1:1,在MeCN水溶液中,在20–25°C下放置48小时),以89-100%的收率得到带有吡咯烷酮和己内酰胺部分的炔属酰胺。该合成涉及由环状am原位形成的胺,其进一步与炔属酯反应。

DBN(1,5-二氮杂双环[4.3.0] non-5-ene)和DBU(1,8-二氮杂双环[5.4.0]十一烷基-7-ene)与炔酸的甲酯和过量的水(反应物)反应摩尔比1:1,在MeCN水溶液中,在20–25°C下放置48小时),以89-100%的收率得到带有吡咯烷酮和己内酰胺部分的炔属酰胺。该合成涉及由环状am原位形成的胺,其进一步与炔属酯反应。

更新日期:2017-12-07
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