Convergent Synthesis of N,S-bis Glycosylquinolin-2-ones via a Pd-G3-XantPhos Precatalyst Catalysis

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Wafa RedjdalSamir Messaoudi

Abstract

Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with α- or β-3-iodo-N-glycosylquinolin-2-ones has been accomplished under mild and operationally simple reaction conditions through the use of a Pd-G3 XantPhos palladacycle precatalyst. This new methodology has been successfully applied to a variety of α- or β-mono-, di-, and poly-thiosugar derivatives to efficiently synthesize a series of α- or β-N,S-bis-glycosyl quinolin-2-ones, which are difficult to synthesize by classical methods.

References

Mar 28, 1996·Chemical Reviews·Raymond A. Dwek
Nov 14, 2002·Chemical Reviews·Hans-Joachim Knölker, Kethiri R Reddy
Dec 12, 2002·Journal of the American Chemical Society·Artis Klapars, Stephen L Buchwald
Mar 18, 2004·Bioorganic & Medicinal Chemistry Letters·Piyasena HewawasamSteven I Dworetzky
Mar 17, 2006·Journal of Medicinal Chemistry·Katri H RaitioTapio Nevalainen
May 17, 2007·International Journal of Medical Sciences·Francisco CastanedaRolf K-H Kinne
May 10, 2013·Organic Letters·Guillaume Mata, Nathan W Luedtke
Aug 10, 2013·Chemical Communications : Chem Comm·Alexandre BruneauSamir Messaoudi
Sep 24, 2013·Organic & Biomolecular Chemistry·Jacques RodrigueRené Roy
Oct 11, 2013·Chemistry : a European Journal·Etienne BrachetSamir Messaoudi
Apr 15, 2016·Organic Letters·Thi Thanh Huyen LuongSamir Messaoudi
Aug 26, 2016·Chemistry : a European Journal·Amélie ChabrierSamir Messaoudi
Jun 10, 2017·The Journal of Organic Chemistry·Riyadh Ahmed Atto Al-ShuaeebSamir Messaoudi
Sep 14, 2017·Organic Letters·Nicolas ProbstSamir Messaoudi
Dec 6, 2017·Chemistry : a European Journal·Nicolas ProbstSamir Messaoudi

❮ Previous
Next ❯

Citations

Jul 31, 2019·Medicinal Research Reviews·Alice TamburriniAnna Bernardi
Jul 11, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Philippe Compain
Apr 14, 2019·Pharmaceuticals·Rachel Hevey

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR
silica
gel column chromatography

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.