A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives
摘要:
Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.
Reusable Co-nanoparticles for general and selective <i>N</i>-alkylation of amines and ammonia with alcohols
作者:Zhuang Ma、Bei Zhou、Xinmin Li、Ravishankar G. Kadam、Manoj B. Gawande、Martin Petr、Radek Zbořil、Matthias Beller、Rajenahally V. Jagadeesh
DOI:10.1039/d1sc05913k
日期:——
A general cobalt-catalyzed N-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generated in situ by mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based
Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.