钯催化脱羧偶联反应合成基于喹啉酮、色酮和香豆素骨架的双杂环化合物

Synthesis of Biheterocycles Based on Quinolinone, Chromone, and Coumarin Scaffolds by Palladium-Catalyzed Decarboxylative Couplings.

作者信息

Vardhan Reddy K Harsha, Brion Jean-Daniel, Messaoudi Samir, Alami Mouad

机构信息

Univ. Paris-Sud, CNRS, BioCIS-UMR 8076, Laboratoire de Chimie Thérapeutique, Equipe Labellisée Ligue Contre Le Cancer, LabEx LERMIT, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, F-92296, France.

出版信息

J Org Chem. 2016 Jan 15;81(2):424-32. doi: 10.1021/acs.joc.5b02103. Epub 2015 Dec 28.

DOI:10.1021/acs.joc.5b02103

PMID:26691351

Abstract

An efficient Pd-catalyzed decarboxylative coupling of heterocyclic carboxylic acids with heterocyclic halides to achieve the synthesis of biheterocycles of biological interest has been reported. In all cases, the cross-coupling reactions take place rapidly in DMSO in good yields and efficiently proceed in the presence of a PdBr2/DPEphos catalytic system, furnishing the novel biheterocycles based on quinolin-4-one, quinolin-2-one, chromone, and coumarin scaffolds.

摘要

据报道，一种高效的钯催化杂环羧酸与杂环卤化物的脱羧偶联反应可实现具有生物学意义的双杂环化合物的合成。在所有情况下，交叉偶联反应在二甲基亚砜中迅速发生，产率良好，并且在PdBr₂/DPEphos催化体系存在下能有效进行，生成基于喹啉-4-酮、喹啉-2-酮、色酮和香豆素骨架的新型双杂环化合物。