98351-87-2

Upstream product

• 98351-97-4 (4-Chloro-biphenyl-2-yl)-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-amine 
• 14774-77-7 p-methoxyphenyllithium 
• 89346-58-7 4′-chloro-1,1′-biphenyl-2yl-carbonitrile 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 4387-36-4 2-iodobenzonitrile 
• 3930-83-4 o-iodobenzamide 
• 609-67-6 2-Iodobenzoyl chloride 
• 88-67-5 2-Iodobenzoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 90-48-2 4-chloro[1,1'-biphenyl]-2-amine 

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.

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.