利用微波辐射合成2-烷基取代的色酮衍生物

Synthesis of 2-alkyl-substituted chromone derivatives using microwave irradiation.

作者信息

Fridén-Saxin Maria, Pemberton Nils, Andersson Krystle da Silva, Dyrager Christine, Friberg Annika, Grøtli Morten, Luthman Kristina

机构信息

Department of Chemistry, Medicinal Chemistry, University of Gothenburg, SE-41296 Goteborg, Sweden.

出版信息

J Org Chem. 2009 Apr 3;74(7):2755-9. doi: 10.1021/jo802783z.

DOI:10.1021/jo802783z

PMID:19323574

Abstract

A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using diisopropylamine in EtOH at 170 degrees C for 1 h gave moderate to high yields (43-88%). The 4-chromanones could be further converted into highly functionalized 2,3,6,8-tetrasubstituted chromones in which a 3-substituent (acetate, amine, or bromine) was introduced via straightforward chemical transformations.

摘要

对2-羟基苯乙酮与脂肪醛之间的碱促进缩合反应进行了研究。该反应已通过微波加热进行优化，以高效方式得到2-烷基取代的4-色满酮。在170℃下于乙醇中使用二异丙胺进行反应1小时，产率为中等至较高（43-88%）。4-色满酮可进一步转化为高度官能化的2,3,6,8-四取代色酮，其中通过直接的化学转化引入了一个3-取代基（乙酸酯、胺或溴）。