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

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.

Metal-Free Iodine(III)-Promoted Synthesis of Isoquinolones

“…A clear majority of those approaches employed transition metal catalysts, such as palladium, rhodium, ruthenium, and nickel catalysts (Scheme ). Palladium catalyst has been widely applied in the reaction of prefunctionalized substrates, including highly reactive intermediate acyl azide . Similar high energy species benzotriazinone has recently been transformed into isoquinolone by nickel catalyst .…”

X-BAND EPR STUDIES OF GAMMA IRRADIATED A NEW ISOQUINOLINE SULFONAMIDE: C17H20BrNO3S

“…Isoquinolines particularly are important heterocyclic X-Band EPR Studies of Gamma Irradiated A New Isoquinoline Sulfonamide: C17H20BrNO3S ICCEES 2020: 1 st International Conference on Computer, Electrical and Electronic Sciences konferansında sunulan bildiriler arasından seçilmiştir. (8-10 Ekim 2020 Konya, TÜRKİYE) 47 motifs; its derivatives also have been identified as ligands for a variety of receptors and as agents for the treatment of a number of pathologies (Glushkov and Shklyaev (2001), Dieudonne et al (2012), Pettit et al (2003)). On the other hand, sulfonamides are also widely used class of compounds as anti-inflammatory and antiviral agents, therefore general and efficient synthesis of sulfonamides under mild conditions is of continuing interest among pharmacists (Jafarppour et al (2011, Scozzafava et al (2003), Greenfield and Grosanu (2008)).…”

IMDAF/Aromatization Path of Halogenated Furylacrylamides and Furylpropiolamides to Dihydroisoquinolin-1(2H)-ones

“…Isoquinolin-1­(2 H )-ones are important heterocyclic motifs in medicinal chemistry. Actually, isoquinolin-1­(2 H )-one derivatives have been identified as ligands for a variety of receptors and as agents for the treatment of a number of pathologies. , Our work in isoquinolinones originated from our interest in pancratistatin ( 4 , Figure ), , one of the most significant antitumoral constituents of Amaryllidaceae. This group of natural products, of which general structure I (Figure ) features a dihydroisoquinolin-1­(2 H )-one substructure (rings A and B), are in fact commonly referred to as the “isocarbostyrils”, , thus highlighting their A-B isoquinolinone part over the fused aminocyclohexitol subunit (ring C) …”