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KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-03-25 , DOI: 10.3762/bjoc.16.44
Qiao Lin , Shiling Zhang , Bin Li

An efficient and simple KOt-Bu-promoted selective ring-opening N-alkylation of 2-methyl-2-oxazoline or 2-(methylthio)-4,5-dihydrothiazole with benzyl halides under basic conditions is described for the first time. The method provides a convenient and practical pathway for the synthesis of versatile 2-aminoethyl acetates and N-substituted thiazolidinones with good functional group tolerance and selectivity. KOt-Bu not only plays an important role to promote this ring-opening N-alkylation, but also acts as an oxygen donor.

中文翻译:

KOt-Bu促进的2-恶唑啉的选择性开环N-烷基化反应获得2-氨基乙酸乙酯和N-取代的噻唑烷酮

首次描述了碱性条件下2-甲基-2-恶唑啉或2-(甲硫基)-4,5-二氢噻唑与苄基卤化物的有效且简单的KO t -Bu促进的选择性开环N-烷基化。该方法为合成具有良好官能团耐受性和选择性的通用2-氨基乙酸乙酯和N-取代的噻唑烷酮提供了方便实用的途径。KO t -Bu不仅在促进该开环N-烷基化中起重要作用,而且还充当氧供体。
更新日期:2020-03-26
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