具有两个多样性位点的3-羟基-6-硝基喹啉-4(1H)-酮的固相合成

Solid-phase synthesis of 3-hydroxy-6-nitroquinolin-4(1H)-ones with two diversity positions.

作者信息

Krupková Sona, Soural Miroslav, Hlavác Jan, Hradil Pavel

机构信息

Department of Organic Chemistry, Faculty of Science, University of Palacky, 771 46 Olomouc, Czech Republic.

出版信息

J Comb Chem. 2009 Nov-Dec;11(6):951-5. doi: 10.1021/cc900068w.

DOI:10.1021/cc900068w

PMID:19778035

Abstract

The efficient solid-phase synthesis of 3-hydroxy-2,7-disubstituted-6-nitroquinolin-4(1H)-ones using Rink amide resin is described. Synthesis starts from immobilized 4-chloro-5-nitroanthranilic acid which, after the nucleophilic replacement of the chlorine atom with various amines and subsequent esterification with bromoacetophenones, afforded substituted phenacylanthranilates. Their cyclization by heating in sulfuric acid gave corresponding hydroxyquinolinones of excellent purity.

摘要

描述了使用Rink酰胺树脂高效固相合成3-羟基-2,7-二取代-6-硝基喹啉-4(1H)-酮的方法。合成从固定化的4-氯-5-硝基邻氨基苯甲酸开始，在将氯原子用各种胺进行亲核取代并随后用溴代苯乙酮酯化后，得到取代的苯甲酰基邻氨基苯甲酸酯。它们在硫酸中加热环化得到纯度优异的相应羟基喹啉酮。