A new palladium-catalyzed oxidative carbamoylation reaction of isoquinoline N-oxides with formylamides for the synthesis of isoquinoline-1-carboxamides is established. The method represents the first example of the carbamoylation of isoquinoline N-oxides with formylamides to furnish arylamides using the dual C-H oxidation strategy.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c4cc10140e | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Isoquinolinequinone N-oxides with diverging mechanisms of action induce collateral sensitivity against multidrug resistant cancer cells.
Eur J Pharmacol
February 2025
i3S - Instituto de Investigação e Inovação em Saúde, Universidade do Porto, 4200-135, Porto, Portugal; Cancer Drug Resistance Group, IPATIMUP - Institute of Molecular Pathology and Immunology, University of Porto, 4200-135, Porto, Portugal; FFUP - Faculty of Pharmacy of the University of Porto, 4050-313, Porto, Portugal. Electronic address:
Multidrug resistance (MDR) is a major challenge in cancer research. Collateral sensitizers, compounds that exploit the enhanced defense mechanisms of MDR cells as weaknesses, are a proposed strategy to overcome MDR. Our previous work reported the synthesis of two novel Isoquinolinequinone (IQQ) N-oxides that induce collateral sensitivity in MDR ABCB1-overexpressing non-small cell lung cancer (NSCLC) and colorectal cancer cells.
View Article and Find Full Text PDFSynthesis of Quinoline-Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between -Oxides and -Alkynylanilines.
Org Lett
December 2024
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea.
The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline -oxides with -alkynylanilines in the presence of a combination of copper(II) catalyst and a bidentate 2,2'-bipyridine ligand is described. The utility of this method was demonstrated through site-selective functionalization of the synthesized products. A plausible reaction pathway for site-selective amination followed by annulative indole formation was elucidated by a series of mechanistic investigations.
View Article and Find Full Text PDFWater-Soluble Bimodal Magnetic-Fluorescent Radical Dendrimers as Potential MRI-FI Imaging Probes.
ACS Appl Mater Interfaces
November 2024
Institut de Ciència de Materials de Barcelona, ICMAB-CSIC, Campus UAB, E-08193 Bellaterra, Spain.
Dual or multimodal imaging probes have become potent tools for enhancing detection sensitivity and accuracy in disease diagnosis. In this context, we present a bimodal imaging dendrimer-based structure that integrates magnetic and fluorescent imaging probes for potential applications in magnetic resonance imaging and fluorescence imaging. It stands out as one of the rare examples where bimodal imaging probes use organic radicals as the magnetic source, despite their tendency to entirely quench fluorophore fluorescence.
View Article and Find Full Text PDFDiscovery of Potent Isoquinolinequinone -Oxides to Overcome Cancer Multidrug Resistance.
J Med Chem
August 2024
School of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork T12 K8AF, Ireland.
Multidrug resistance (MDR) of human tumors has resulted in an immediate need to develop appropriate new drugs. This work outlines the development of 20 potent IQQ -oxide derivatives in two isomeric families, both exhibiting nanomolar GI against human tumor cell lines. Preliminary NCI-60 tumor screening sees the C(6) isomers achieve a mean GI > 2 times lower than the corresponding C(7) isomers.
View Article and Find Full Text PDFSynthesis of Selenium-Decorated -Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions.
J Org Chem
August 2024
Centro de Ciências Químicas, Farmacêuticas e de Alimentos (CCQFA), Universidade Federal de Pelotas (UFPel), P.O. Box 354, Pelotas, 96010-900 Rio Grande do Sul, Brazil.
Herein, we describe the use of benzeneseleninic acid derivatives (BSA) as a bench-stable and easy to handle selenium reagent to access 4-(selanyl)isoquinoline--oxides through the selenocyclization of -alkynyl benzaldehyde oximes. The reaction is conducted in refluxing methanol, allowing the thermal generation of electrophilic selenium species in situ. By this new protocol, a library of 19 selenium-decorated -oxide isoquinolines was accessed in up to 96% yield with an outstanding substrate tolerance and the feasibility to scale it up 10 times (from 0.
View Article and Find Full Text PDFWant 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!