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Relevant academic research and scientific papers

Preparation of phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin

Treatment of N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin in 1,2-dichloroethane under irradiation with a tungsten lamp, followed by the reaction with tBuOK gave the corresponding 6-arylphenanthridines and 6-unsubstituted phenanthridines in good to moderate yields, respectively. The reaction proceeds through an oxidative cyclization onto the aromatic ring by sulfonamidyl radicals formed from the N-iodosulfonamides. The present reaction is a one-pot method for the preparation of both 6-arylphenanthridines and 6-unsubstituted phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides under transition-metal-free conditions.

ORGANIC COMPOUND, ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME AND DISPLAY INCLUDING THE ORGANIC LIGHT EMITTING DIODE

The present invention provides an organic compound represented by Chemical Formula 1 below: In Chemical Formula 1, R1 to R9 are each, independently, any one selected from the group consisting of hydrogen, a halogen, a nitro group, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C6-C40 aryl group, and a substituted or unsubstituted C5-C40 heteroaryl group; L represents a single bond and is any one selected from the group consisting of an alkylene group, a cycloalkylene group, a heterocycloalkylene group, an arylene group, and a heteroarylene group; and Ar1 and Ar2 are each, independently, any one selected from the group consisting of hydrogen, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C3-C6 heterocycloalkyl group, a substituted or unsubstituted C6-C40 aryl group, and a substituted or unsubstituted C2-C40 heteroaryl group. According to the present invention, the light emitting efficiency, stability, and lifetime of an organic light emitting diode may be improved.

MANUFACTURING METHOD OF PHENANTHRIDINE COMPOUND

PROBLEM TO BE SOLVED: To provide a manufacturing method of a phenanthridine compound enhancing manufacturing easiness and reducing manufacturing cost. SOLUTION: There is provided a manufacturing method for mixing an imine compound of the following formula and an iodination agent. R1 is an aliphatic group or an aromatic group, R2 to R9 are H, a halogen atom, a linear or branched alkyl group with 1 to 12 carbon atoms, which may be substituted, an aromatic group which may be substituted, or the like, and may form aromatic or non-aromatic ring by binding each other. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

6-Arylphenanthridines from Aryl o-Biaryl Ketones with 1,1,1,3,3,3-Hexamethyldisilazane and Molecular Iodine

Warming treatment of aryl o-biaryl ketones with 1,1,1,3,3,3-hexamethyldisilazane in the presence of Sc(OTf)3 in toluene, followed by the reaction with molecular iodine and K2CO3 in a mixture of THF and methanol at 60 °C gave the corresponding 6-arylphenanthridines in good to moderate yields. The present reaction is a one-pot method for the preparation of 6-arylphenanthridines from aryl o-biaryl ketones through the cyclization of imino-nitrogen-centered radicals that were generated from N-iodo aryl o-biaryl ketimines formed from the reaction of aryl biaryl ketimines with molecular iodine.

Preparation of Phenanthridines from o-Cyanobiaryls via Addition of Organic Lithiums to Nitriles and Imino Radical Cyclization with Iodine

Simple treatment of 2-cyanobiaryls with methyllithium, ethylmagnesium bromide, butyllithium, phenyllithium, p-methylphenyllithium, etc., followed by the reaction with water and then with molecular iodine at 60 °C provided efficiently 6-methyl-, 6-ethyl-, 6-butyl-, 6-phenyl, 6-(p-methylphenyl)phenanthridines, etc., in good yields, respectively. Here, imines formed through the addition of carbanion onto the nitriles reacted with molecular iodine to form N-iodoimines smoothly, and their warming treatment induced the formation of imino radicals that smoothly cyclized onto the aryl group to give 6-alkyl- and 6-arylphenanthridines.

Arylative cyclization of 2-isocyanobiphenyls with anilines: One-pot synthesis of 6-arylphenanthridines via competitive reaction pathways

A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.

Synthesis of phenanthridine derivatives via cascade annulation of diaryliodonium salts and nitriles

A cascade coupling reaction toward a variety of phenanthridine derivatives has been developed. This cascade transformation proceeds via the copper-catalyzed coupling reaction of diaryliodonium salts and nitriles, and undergoes cyclization into the phenanthridine core.