Synthesis of substituted isoquinolines via Pd-catalyzed cross-coupling approaches.

Org Lett

Department of Chemistry and Chemical Biology, McMaster University, Hamilton, Ontario, Canada, L8S 4M1.

Published: December 2011

Palladium complexes incorporating ligands based on a 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantanyl scaffold were used to catalyze the arylation of ethyl cyanoacetate, malononitrile, and various ketones. The products from these reactions can be elaborated to substituted β-arylethylamines and used in microwave-assisted Pictet-Spengler reactions. The protocol developed is suitable for the synthesis of libraries of substituted isoquinolines.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol202565jDOI Listing

Publication Analysis

Top Keywords

substituted isoquinolines
8
synthesis substituted
4
isoquinolines pd-catalyzed
4
pd-catalyzed cross-coupling
4
cross-coupling approaches
4
approaches palladium
4
palladium complexes
4
complexes incorporating
4
incorporating ligands
4
ligands based
4

Similar Publications

The isoquinoline core is present in one of the largest subsets of bioactive natural products. The multifunctional isoquinoline core exerts diverse bioactivity, resulting in the development of numerous isoquinoline-based drugs and molecules that are currently under clinical trials. We developed a new approach for phosphite-mediated [1,2] alkyl migration for an overall -C-H alkylation -alkylation of isoquinoline.

View Article and Find Full Text PDF

We disclosed an efficient protocol for regioselective C6 C-H/N-H activation/annulation reaction of indole-7-carboxamides with alkynes to synthesize highly substituted pyrrolo[3,2-h]isoquinolin-9-one derivatives. Under optimized reaction conditions, electron-deficient and electron-rich internal alkynes reacted efficiently with various indole-7-carboxamides to deliver desired products in good to excellent yields. The synthetic utility of the product is demonstrated by its selective oxidation to the corresponding isatin derivative.

View Article and Find Full Text PDF

Recent studies have discovered that aryl-substituted pyrido[2,1-a]isoquinolines have the potential to be highly active DPP IV inhibitors. In previous studies, we reported a novel synthetic approach for the construction of their sulfur-containing bioisosteric [1,4]thiazino[3,4-a]isoquinolines analogues, incorporating an additional aryl substituent. The present study aims to investigate the DPP IV inhibitory activity and cytotoxicity of the synthesized molecules by in vitro assay.

View Article and Find Full Text PDF

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light.

Beilstein J Org Chem

October 2024

Department of Chemistry and Industrial Chemistry, University of Genoa, Via Dodecaneso 31, 1646 Genova, Italy.

Spiro-heterocyclic indolenines are privileged scaffolds widely present in numerous indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of -aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which reacts with an isocyanide and an electron-rich aniline in a three-component Ugi-type reaction to give an α-aminoamidine.

View Article and Find Full Text PDF

Hypertension Induced by Hypoxia-Inducible Factor Prolyl Hydroxylase Inhibitors in Treating Anemia in Patients With Chronic Kidney Disease: A Mini-Review.

J Clin Hypertens (Greenwich)

December 2024

Department of Cardiovascular Medicine, State Key Laboratory of Medical Genomics, Shanghai Key Laboratory of Hypertension, Shanghai Institute of Hypertension, Ruijin Hospital, Shanghai Jiao Tong University School of Medicine, Shanghai, China.

Hypoxia-inducible factor prolyl hydroxylase (HIF-PH) inhibitors are a new class of agents for the treatment of anemia in chronic kidney disease (CKD). Unlike traditional treatments such as erythropoiesis-stimulating agents (ESAs), HIF-PH inhibitors are orally administered drugs and may increase endogenous erythropoietin and improve iron homeostasis. However, a significant concern is their possible side effect on blood pressure.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!