Herein, a novel route to atropisomeric -aryl quinolones with low rotational barriers is demonstrated, leveraging a dual photochemical/organocatalytic approach to the required ring closure in up to 94% yield and up to >99% ee. The use of a continuous flow system allows for impurity suppression and enables rapid scale-up to a decagram scale.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.3c02117 | DOI Listing |
ACS Omega
November 2024
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355017, Russia.
A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly of complex (dihydro)indolo[1,2-]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation of 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones to the corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. The latter can either be isolated with good yields (75-96%) or, in the case of -nitroacetophenone, used for further base-assisted intramolecular SAr cyclization resulting in indoxyl-fused quinolone-4 hybrids (up to 95%).
View Article and Find Full Text PDFChemistry
November 2024
Department of Chemistry, Rice University, Houston, Texas, 77030, USA.
For decades, the synthesis of 2-quinolones, a crucial structural motif in pharmaceuticals and agrochemicals, has relied heavily on costly noble metal complexes and structurally complex ligands. Despite considerable efforts from synthetic chemists, a mild, metal-free, environmentally friendly, and cost-effective approach has remained elusive. This study introduces a robust, metal-free synthetic platform that leverages an innovative organoiodine-catalyzed electrophilic arene C(sp)-H amination strategy to efficiently produce a wide range of new and modifiable 2-quinolones.
View Article and Find Full Text PDFSci Rep
October 2024
Department of Molecular Biotechnology and Health Sciences, University of Torino, via Nizza 44bis, 10126, Turin, Italy.
P. aeruginosa employs specific quorum sensing (QS) mechanisms to orchestrate biofilm formation, enhancing resistance to host defences. In physiological conditions, QS molecules permeate the lung environment and cellular membrane to reach the cytoplasmic Aryl Hydrocarbon Receptor (AhR) that is pivotal for activating the immune response against infection.
View Article and Find Full Text PDFMedicina (Kaunas)
October 2024
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
Chem Soc Rev
November 2024
Department of Chemistry, Ludwig-Maximilians-University München, Butenandtstrasse 5-13, Haus F, 81377 Munich, Germany.
This review highlights the use of functionalized organo-Li, -Mg and -Zn reagents for the construction and selective functionalization of 5- and 6-membered fused bicyclic heteroaromatics. Special attention is given to the discussion of advanced syntheses for the preparation of highly functionalized heteroaromatic scaffolds, including quinolines, naphthyridines, indoles, benzofurans, benzothiophenes, benzoxazoles, benzothiazoles, benzopyrimidines, anthranils, thienothiophenes, purine coumarins, chromones, quinolones and phthalazines and their fused heterocyclic derivatives. The organometallic reagents used for the desired functionalizations of these scaffolds are generally prepared using the following methods: (i) through directed selective metalation reactions (DoM), (ii) by means of halogen/metal exchange reactions, (iii) through oxidative metal insertions (Li, Mg, Zn), and (iv) by transmetalation reactions (organo-Li and Mg transmetalations with ZnCl or ZnO(Piv)).
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!