37993-76-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenylisoquinoline is used as a ligand for the synthesis of various organic light-emitting diode (OLED) dopants. Its unique chemical structure allows it to be a crucial element in the development of advanced materials for pharmaceutical applications, particularly in the field of drug delivery systems.
Used in Electronics Industry:
In the electronics industry, 3-Phenylisoquinoline is utilized as a ligand for synthesizing OLED dopants. These dopants are essential in the production of OLEDs, which are widely used in display technologies such as televisions, smartphones, and other electronic devices. 3-PHENYLISOQUINOLINE's role in creating efficient and high-quality OLEDs contributes to the advancement of electronic display technology.
Used in Chemical Research:
3-Phenylisoquinoline serves as a valuable compound in chemical research, particularly in the study of organic chemistry and the development of new synthetic methods. Its unique structure and properties make it an interesting subject for researchers to explore and potentially discover new applications and uses in various fields.

Synthesis Reference(s)

Tetrahedron Letters, 13, p. 3149, 1972 DOI: 10.1016/S0040-4039(01)93988-7

InChI:InChI=1/C15H11N/c1-2-6-12(7-3-1)15-10-13-8-4-5-9-14(13)11-16-15/h1-11H

Upstream product

• 136918-14-4 phthalimide 
• 55150-54-4 1-chloro-3-phenylisoquinoline 
• 101283-79-8 [2-(benzoylamino-methyl)-phenyl]-acetic acid 
• 119-65-3 isoquinoline 
• 23586-54-1 phenylthalium(III) di(trifluoroacetate) 
• 60815-16-9 2-(o-formylphenyl)-1-phenylethanone 
• 35447-99-5 1,2-dihydrobenzocyclobuten-1-ol 
• 100-47-0 benzonitrile 
• 10034-85-2 hydrogen iodide 
• 480-91-1 oxisoindole 
• 7115-13-1 3-phenylisoquinoline-1-ol 
• 59046-72-9 o-(phenylethynyl)benzaldehyde 
• 696-62-8 para-iodoanisole 
• 58313-23-8 3-iodobenzoic acid methyl ester 

Downstream Products

• 63144-54-7 2-methyl-3-phenyl-isoquinolinium; iodide 
• 51787-71-4 3-phenylisoquinoline 2-oxide 
• 1379667-42-1 N-[2-(isoquinolin-3-yl)phenyl]-4-methylbenzenesulfonamide 
• 1443309-10-1 C₂₂H₁₈N⁽¹⁺⁾*Br^(1-) 
• 1443309-07-6 C₂₆H₂₄NO₂⁽¹⁺⁾*Br^(1-) 
• 1443308-89-1 N-(2-isopropylcarbonylbenzyl)-3-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1443309-13-4 C₂₂H₂₁N 
• 1443309-11-2 C₂₂H₁₉N 
• 146530-36-1 (R)-3-phenyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Palladium-catalyzed domino Heck/intermolecular cross-coupling: efficient synthesis of 4-alkylated isoquinoline derivatives

A highly efficient Pd-catalyzed Heck-type cascade process with 2-(1-alkynyl)benzaldimines has been developed, which provides access to a broad range of 4-alkylated isoquinoline derivatives in moderate to good yields. The σ-alkylpalladium(ii) intermediate in the Heck reaction activates alkynes toward intramolecular nucleophilic attack. This is the first example of a σ-alkylpalladium(ii) intermediate promoting the cyclization of alkynes containing a proximate nucleophilic center.

Copper-Catalyzed [4+2]-Cycloadditions of Isoxazoles with 2-Alkynylbenzaldehydes To Access Distinct α-Carbonylnaphthalene Derivatives: C(3,4)-versus C(4,5)-Regioselectivity at Isoxazoles

Cu(II)-catalyzed [4+2]-cycloadditions occur between Cu-benzopyryliums and substituted isoxazoles with the regioselectivity on the C(3,4)-carbons of isoxazoles. We postulate that a prior coordination of isoxazoles with Cu(OAc)2 increases the ?-bond character of the C(3,4) carbons to become an effective 2?-donor. In this reaction sequence, 3,5-disubstituted isoxazoles yield α,?-dicarbonylnaphthalenes whereas, 5-substituted isoxazoles deliver α,?-dicarbonyl-β-aminonaphthalenes. For unsubstituted isoxazole, its cycloaddition chemoselectivity is switched to the C(4,5)-addition regioselectivity to yield α-carbonyl-?-cyanonaphthalene derivatives.

Reaction of Benzocyclobutenoxides with Nitriles: Synthesis of Hypecumine and Other 3-Substituted Isoquinolines

Treatment of benzocyclobuten-2-ols with MeLi affords o-tolualdehyde anions which in the presence of nitriles cyclize to 3-substituted isoquinolines.Examples include the synthesis of the alkaloid hypecumine from the precursors, 14 and 19 (1:1), in 50percen

Synthesis of 4-(1: H -isochromen-1-yl)isoquinolines through the silver-catalysed homodimerization of ortho -alkynylarylaldehydes and subsequent condensation of the 1,5-dicarbonyl motif with NH3

4-(1H-Isochromen-1-yl)isoquinoline derivatives were synthesized in high yields via the AgBF4-catalyzed self-reaction of ortho-alkynylarylaldehydes to give isochromene intermediates, followed by the dehydration of the 1,5-dicarbonyl motif with NH3. Compared with electron-rich aromatic substituents, this strategy can provide the desired isochromene products with an electron-deficient isoquinoline unit. The reactions feature simple experimental operations, mild reaction conditions and high product yields.

Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues

A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw

Facile preparation of 3-aryl-4-iodoisoquinolines from N-(o-Arylethynyl)benzyl p-toluenesulfonamides with iodine and base

Treatment of N-(o-arylethynyl)benzyl p-toluenesulfonamides with molecular iodine in the presence of NaHCO3 at 60 °C, followed by the reaction with tBuOK at room temperature gave 3-aryl-4-iodoisoquinolines in good yields. 4-Iodo-3-phenylisoquinoline, which is one of the obtained 3-aryl-4-iodoisoquinolines, was further transformed into isoquinoline derivatives smoothly. The present approach is a novel one-pot method for the preparation of 3-aryl-4-iodoisoquinolines from N-(o-arylethynyl)benzyl p-toluenesulfonamides under transition-metal-free conditions.

Silver/Rhodium Relay Catalysis Enables C?H Functionalization of In Situ Generated Isoquinolines with Sulfoxonium Ylides: Construction of Hexahydrodibenzo[a,g]quinolizine Scaffolds

Employing silver/rhodium relay catalysis strategy, an intramolecular electrophilic cyclization and C?H activation followed by cascade hydrogenation and reductive amination has been developed. The acylmethylated isoquinoline derivatives could be afforded with broad substrate scope in 23–88% yields, which could be further transformed to the core skeleton of hexahydrodibenzo[a,g]quinolizine as drug-candidates. Moreover, this reaction was achieved in a gram-scale. A reasonable reaction mechanism has been proposed based on a series of control and KIE experiments. (Figure presented.).

Synthesis of N-(isoquinolin-1-yl)sulfonamides via Ag2O-catalyzed tandem reaction of ortho-alkynylbenzaldoximes with benchtop stabilized ketenimines

In this project, a moderately efficient approach to multisubstituted N-(isoquinolin-1-yl)sulfonamide derivatives was illustrated, utilizing ortho-alkynylbenzaldoximes and zwitterionic ketenimine salts in a tandem reaction catalyzed by silver oxide. The oxophilicity of Ag2O, along with its nature as Lewis acid, pave the way for a smooth [3 + 2] cycloaddition between isoquinoline N-oxides and ketenimine species, which is a key step in this reaction. DFT calculation suggests that 1,3-dipolar cycloaddition of nitrone and ketenimine proceeds through a selective stepwise mechanism.

NHC-Mediated Stetter-Aldol and Imino-Stetter-Aldol Domino Cyclization to Naphthalen-1(2 H)-ones and Isoquinolines

N-Heterocyclic carbene-catalyzed tandem Stetter-aldol reaction of phthalaldehyde and α,β-unsaturated ketimines has been developed to afford functionalized naphthalen-1(2H)-one derivatives as the formal [4+2] annulation product. Interestingly, the reaction of aldimines led to the formation of isoquinoline derivatives instead of the expected indanone derivatives as a [4+1] annulation product.

Dynamic Kinetic Resolution in Gold-Catalyzed (4 + 2)-Annulations between Alkynyl Benzaldehydes and Allenamides to Yield Enantioenriched All-Carbon Diarylalkylmethane Derivatives

This work reports the synthesis of diarylmethane derivatives via gold-catalyzed (4 + 2)-annulations between alkynyl benzaldehydes and allenamides, followed by an aza-Claisen rearrangement. Deuterium labeling and crossover experiments have been performed to confirm this proposed mechanism. With racemic 3-substituted allenamides in a substrate ratio (1:1), we employ chiral gold catalysts to achieve a dynamic kinetic resolution to obtain enantioenriched diarylalkylmethane derivatives with high e.r. levels (up to 93:7).