Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade
摘要:
We developed a one-pot, two-stage synthetic route to substituted 4-aminoquinolines involving an imidoylative Sonogashira coupling followed by acid-mediated cyclization. This three-component reaction affords pharmaceutically valuable 4-aminoquinolines in a one-pot procedure from readily available starting materials. The reaction tolerates various substituents on the arene as well as the use of secondary and even primary isocyanides. Additionally, the wide tolerance for functionalized isocyanides allows for the one-pot synthesis of various substituted chloroquine analogues as well as other medicinally relevant products.
An unusual base-mediated cyclization of ketimines derived from 2-(trifluoromethyl)aniline that involves the trifluoromethyl group: an expedient route to 2-arylquinolines
作者:Lucjan Strekowski、Roman L. Wydra、Marek T. Cegla、Agnieszka Czarny、Donald B. Harden、Steven E. Patterson、Merle A. Battiste、James M. Coxon
DOI:10.1021/jo00303a001
日期:1990.8
STREKOWSKI, LUCJAN;WYDRA, ROMAN L.;CEGLA, MAREK T.;CZARNY, AGNIESZKA;HARD+, J. ORG. CHEM., 55,(1990) N6, C. 4777-4779
作者:STREKOWSKI, LUCJAN、WYDRA, ROMAN L.、CEGLA, MAREK T.、CZARNY, AGNIESZKA、HARD+