Preparation of quinolines from resin-bound esters using titanium reagents

被引:11
作者
Macleod, C
Austin, CA
Hamprecht, DW
Hartley, RC [1 ]
机构
[1] Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland
[2] GlaxoSmithKline, Ctr Ric, I-37135 Verona, Italy
基金
英国工程与自然科学研究理事会;
关键词
Quinolines; titanium and compounds; solid-phase synthesis; thioacetals; Wittig reaction;
D O I
10.1016/j.tetlet.2004.09.170
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
ortho-Amino homobenzylic thioacetals are prepared from ortho-nitrobenzaidehydes via homologation using an alpha-methoxy Wittig reagent. Titanium reagents are generated from the 1,3-dithianes using a low valent titanium reagent and are then used to alkylidenate resin-bound esters. An N-silylated Boc group protects the ortho-amino functionality. Traceless SPS of quinolines is completed by treating the resulting resin-bound enol ethers with TFA and then oxidizing with manganese dioxide to give 2-substituted quinolines in high purity without the need for chromatography. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8879 / 8882
页数:4
相关论文
共 30 条