A new access to 3-substituted-1(2H)-isoquinolone by tandem palladium-catalyzed intramolecular aminocarbonylation annulation

Organic & Biomolecular Chemistry
Antoine Dieudonné-VatranJean-Claude Florent

Abstract

An original tribromide derivative based, palladium-catalyzed synthesis of 3-substituted-1(2H)-isoquinolone is described based on a regioselective Suzuki-Miyaura C-C coupling on o-halo-(2,2-dihalovinyl)-benzene followed by a palladium catalyzed amination-carbonylation-cyclization reaction. This sequence efficiently proceeds to build up isoquinolone in fair to good yields over a one-pot 3-bond synthesis reaction.

References

Sep 4, 1992·Journal of Medicinal Chemistry·T MatsuiK Ohmoto
Nov 1, 1996·The Journal of Organic Chemistry·J. Edward SempleGary Gardner
May 13, 2004·Chemical Reviews·Itaru Nakamura, Yoshinori Yamamoto
May 21, 2004·Organic Letters·Barry M Trost, Michael K Ameriks
Feb 12, 2005·The Journal of Organic Chemistry·Tuanli Yao, Richard C Larock
Apr 28, 2007·Organic & Biomolecular Chemistry·Marc LamblinPierre Grandclaudon
Aug 19, 2007·Chemical Communications : Chem Comm·Venkateswara Rao BatchuManojit Pal
Mar 4, 2008·Bioorganic & Medicinal Chemistry·Yasutomi AsanoShoji Fukumoto
Apr 17, 2008·Journal of the American Chemical Society·Yuichi KajitaTakuya Kurahashi
Aug 30, 2008·The Journal of Organic Chemistry·Joseph R MartinelliStephen L Buchwald
Oct 13, 2009·Journal of Combinatorial Chemistry·Sujata RoyRichard C Larock
Jul 29, 2010·Journal of the American Chemical Society·Todd K Hyster, Tomislav Rovis
Sep 8, 2010·European Journal of Medicinal Chemistry·Su Hui YangWon-Jea Cho
Jan 22, 2011·Bioorganic & Medicinal Chemistry Letters·Peter RayMark York
Feb 1, 2011·Journal of the American Chemical Society·Souvik RakshitFrank Glorius
Apr 2, 2011·Journal of the American Chemical Society·Nicolas GuimondKeith Fagnou
May 26, 2011·Angewandte Chemie·Lutz AckermannNora Hofmann

❮ Previous
Next ❯

Citations

Feb 6, 2013·The Journal of Organic Chemistry·Olaia Nieto-García, Ricardo Alonso
Jan 7, 2016·Chemical Communications : Chem Comm·Aleksandr N Shestakov, Mikhail A Kuznetsov
Oct 25, 2014·The Journal of Organic Chemistry·Zhi-Wei ChenJian-Yu Zheng
Nov 20, 2014·Organic & Biomolecular Chemistry·Wen-Tao WeiMing Yan

❮ Previous
Next ❯

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.