Synthesis Of Isoquinoline Derivatives Research Articles

Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

AbstractThe preservation of scarce rare earth metals, such as palladium, rhodium, iridium, and others, poses a significant challenge for humanity due to their limited availability. These rare earth metals might be replaced by earth‐abundant 3d‐transition metals such as cobalt, manganese, iron, nickel, copper, etc. Isoquinolines have acquired an important position in synthetic organic chemistry as well as medicinal chemistry. They manifest in a diverse range of natural and synthetic molecules, serving as pivotal synthons for the synthesis of numerous bioactive compounds with notable medicinal significance. Numerous reports on the synthesis of isoquinoline derivatives via transition metal catalysis have been published worldwide. In this review, we summarize recent approaches for synthesizing various isoquinoline derivatives using 3d‐transition‐metal catalysts since 2020. The review has been divided into different 3d‐transition‐metal‐based catalysis. We expect that this review will bring a better overview of the present status of the significant progress made in the 3d‐transition‐metal‐based synthesis of isoquinolines and persuade more advancements and research in this area in the near future.

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

AbstractIn the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N‐heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.magnified image

Synthesis of Isoquinoline Derivatives via Palladium‐Catalyzed C−H/C−N Bond Activation of N‐Acyl Hydrazones with α‐Substituted Vinyl Azides

AbstractA palladium‐catalyzed cyclization of N‐acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α‐substituted vinyl azide serves as an internal nitrogen source. Also, C−H bond activation and C−N bond cleavage have been realized using hydrazone as directing group.magnified image

ChemInform Abstract: Synthesis of Isoquinoline Derivatives from β‐Hydroxyarylethanamides (I).

ChemInform Abstract: Synthesis of Isoquinoline Derivatives from β‐Hydroxyarylethanamides (I).

Synthesis of Isoquinoline Derivatives from β-Hydroxyarylethanamides

A simple and efficient protocol for the construction of medicinally important substituted isoquinolines through intramolecular cyclization of β-hydroxyarylethanamides using acetic anhydride and phosphorous pentoxide in dioxane has been described. The chemo- and regioselectivities due to the influence of different catalysts were investigated and optimized for good to excellent yields. All the synthesized compounds have been characterized by NMR and mass spectral analyses.

ChemInform Abstract: Synthesis of Isoquinoline Derivatives Through Rhodium(III)‐Catalyzed Reactions of Benzylamines with Non‐Terminal Alkynes.

AbstractThe Rh(III)‐catalyzed N‐annulation of primary, secondary, and tertiary benzylamines with internal alkynes is developed.

Synthesis of Isoquinoline Derivatives through Rhodium(III)‐ Catalyzed Reactions of Benzylamines with Non‐Terminal Alkynes

AbstractA new rhodium(III)‐catalyzed N‐annulation reaction of benzylamines with internal alkynes has been developed. Observations made during these efforts suggest that the mechanistic pathway followed in this process involves direct participation of benzylamines without their preliminary oxidative dehydrogenation. Moreover, N‐annulation reactions of primary benzylamines result in the formation of mixtures of isoquinolines and 8‐vinylisoquinolines. Finally, secondary and tertiary benzylamines undergo rhodium(III)‐catalyzed N‐annulation reactions to generate the respective isoquinolinium and hydroisoquinolinium salt products.magnified image

Efficient Synthesis of Isoquinoline Derivatives via AgOTf/Cu(OTf)2-Cocatalyzed Cyclization of 2-Alkynyl Benzaldoxime

An efficient, AgOTf and Cu(OTf)2 multicatalytic intramolecular cycloisomerization of 2-alkynylbenzaldoxime is reported. Isoquinoline N-oxides have been found to be deoxygenated to the corresponding quinolines in good yields in dimethylformamide/dichloroethane (v/v 5:1) as solvent at 120 °C.

ChemInform Abstract: Synthesis of Isoquinoline Derivatives by a Tandem Aza-Wittig/ Electrocyclization Strategy and Preparation of the Unknown 1,9- Diazaphenalene Ring by a Consecutive Electrocyclic Ring Closure/ Claisen Rearrangement/ Intramolecular Amina

Treatment of iminophosphrane 3, derived from ethyl α-azido-2-(allyloxy) cinnamate, with aromatic isocyanates in toluene at 150 o C leads to the corresponding isoquinoline derivatives 5 by a tandem electrocyclic ring closure/Claisen rearrangement of the intermediate carbodiimide. Fremy's salt promoted oxidation of compounds 5 yields the 5,8-isoquinolinequinone allides 6, which by heating undergo cyclization to 2H-pyrano [2,3-f] isoquinolines isocyanates to give the corresponding carbodiimides, which by thermal treatment at 150 o C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/intramolecular amination process to give 1,9-diazaphenalene derivatives

ChemInform Abstract: Utility of Activated Nitriles in the Synthesis of Isoquinoline Derivatives.

Abstract γ-Cyano-γ-(4-pyridyl) pimelonitrile (2) has been prepared by cyanoethylation of 4-pyridyl-acetonitrile (1). Hydrolysis of (2) using dil. HCl afford γ- amido-γ-(4-pyridyl) pimelic acid (3) which cyclized to the corresponding 3-(4-pyridyl)-2, 6-piperidindione-3-propionic acid (4) by continuos heating in hydrochloric acid solution. Ring closure of (4) takes place in the presence of conc. sulphuric acid to give spiroisoquinoline derivative (5). Spiroisoquinoline derivatives (8) - (11) have been also prepared. Structure of all the products have been established by elemental and spectral analyses.

ChemInform Abstract: Nickel(0)‐Catalyzed [2 + 2 + 2] Cycloaddition of Diynes and 3,4‐Pyridynes: Novel Synthesis of Isoquinoline Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Synthesis of Isoquinoline Derivatives via Ag‐Catalyzed Cyclization of 2‐Alkynyl Benzyl Azides.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of Isoquinoline Derivatives via Ag- Catalyzed Cyclization of 2-Alkynyl Benzyl Azides

Ag-catalyzed cyclization of 2-alkynyl benzyl azides offers a novel and efficient method for the synthesis of substituted isoquinoline. The reaction proceeds smoothly in moderate to good yields and tolerates considerable functional groups. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed.

Nickel(0)-catalyzed [2 + 2 + 2] cycloaddition of diynes and 3,4-pyridynes: novel synthesis of isoquinoline derivatives

A transition metal-catalyzed [2 + 2 + 2] cycloaddition between alpha,omega-diynes and 3,4-pyridynes has been realized for the first time, producing isoquinolines in good yields by using a nickel(0) catalyst.

2‐(Azidomethyl)phenylboronic Acid in the Synthesis of Isoquinoline Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthesis of Isoquinoline Derivatives Using ROM—RCM of Cyclobutene‐yne.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of Isoquinoline Derivatives Using ROM−RCM of Cyclobutene-yne

Isoquinoline derivatives were synthesized from cyclobutenylmethylamine derivatives having an alkyne moiety in a tether using a second-generation ruthenium carbene complex under ethylene gas in good yields.

New Synthesis of Isoquinoline Derivatives by Reactions of 2‐(2‐Methoxyethenyl)benzonitriles with Organolithiums and Lithium Dialkylamides.

AbstractFor Abstract see ChemInform Abstract in Full Text.

New Synthesis of Isoquinoline Derivatives by Reactions of 2-(2-Methoxyethenyl)benzonitriles with Organolithiums and Lithium Dialkylamides

Abstract A simple and efficient synthesis of 1-alkyl(or aryl)isoquinoline and isoquinolin-1-amine derivatives based on intramolecular cyclization of 2-(2-methoxyethenyl)benzonitriles initiated by the addition of alkyl(or aryl)lithiums and lithium dialkylamides to the nitrile carbons, respectively, is described.

ChemInform Abstract: Synthesis of Isoquinoline Derivatives by Diels—Alder Reactions of 2(1H)‐Pyridones Having and Electron‐Withdrawing Group with Methoxy‐1,3‐butadienes.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.