2720-93-6

Usage

InChI:InChI=1/C19H13N/c1-2-8-14(9-3-1)19-17-12-5-4-10-15(17)16-11-6-7-13-18(16)20-19/h1-13H

Upstream product

• 229-87-8 phenanthridine 
• 591-51-5 phenyllithium 
• 52648-48-3 N-(phenylmethyl)-(1,1'-biphenyl)-2-amine 
• 7404-97-9 2-(benzoylamino)biphenyl 
• 90-41-5 2-phenylaniline 
• 98-07-7 Benzotrichlorid 
• 13355-64-1 5-phenyl-5,6-dihydrophenanthridine 
• 14548-01-7 phenanthridine N-oxide 
• 58469-04-8 N-(Phenylmethylene)-(1,1'-biphenyl)-2-amine 
• 16864-88-3 1,2,3,4,7,8,9,10-octahydro-6-phenylphenanthridine 
• 97389-42-9 6-phenyl-7,8,9,10-tetrahyrophenanthridin-7-one 
• 83913-73-9 9-azido-9-phenyl-fluorene 
• 3128-77-6 2-isocyanobiphenyl 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 15263-58-8 2-phenyl-3,4-benzoquinoline N-oxide 
• 97692-18-7 6,6'-diphenyl-5',6'-dihydro-[4,6']biphenanthridinyl 
• 22364-47-2 6,6-diphenyl-5,6-dihydro-phenanthridine 
• 127563-62-6 5-methyl-6-phenyl-phenanthridinium; methyl sulfate 
• 102548-87-8 6-allyl-6-phenyl-5,6-dihydro-phenanthridine 
• 832-68-8 6-aminophenanthridine 
• 56243-27-7 6-phenyl-5,6-dihydrophenanthridine 
• 6338-91-6 5-methyl-6-phenyl-phenanthridinium; iodide 
• 1373484-50-4 [6-2H]-5-methyl-6-phenyl-5,6-dihydrophenanthridine 
• 1373484-43-5 5-methyl-6-phenylphenanthridinium perchlorate 
• 872809-63-7 2-chloro-6-phenylphenanthridine 

Relevant academic research and scientific papers

Photoredox catalysis using infrared light via triplet fusion upconversion

Recent advances in photoredox catalysis have made it possible to achieve various challenging synthetic transformations, polymerizations and surface modifications1–3. All of these reactions require ultraviolet- or visible-light stimuli; however,

Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes

The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.

Method for rapidly synthesizing phenanthridine compounds

The invention discloses a method for rapidly synthesizing phenanthridine compounds. The method comprises the following steps of: uniformly mixing 9-fluorenol 1 serving as a starting raw material and azide 2 in a solvent at room temperature, slowly dropwis

Ring-Expansion Strategy for α-Aryl Azahelicene Construction: Building Blocks for Optoelectronic Materials

An acid-mediated rapid synthesis of α-aryl azahelicenes via C-C bond cleavage of helical 9H-fluoren-9-ols is reported. The newly introduced aryl ring and pyridine moieties provide an excellent opportunity to further tune the properties of azahelicences: i.e., photoluminescence. The novel α-aryl azahelicenes showcase high circularly polarized luminescence (CPL) efficiencies (4.5 × 10-3) as well as CPL brightness (BCPL), reaching 7.39 M-1 cm-1, which indicates a potential application as chiral emitters.

Construction of 2-Amino-2′-ketonyl Biaryls via Acid-Mediated Ring Opening of 9 H-Fluoren-9-ols with Organic Azides

A direct cross-coupling between 9H-fluoren-9-ols and organic azides for the synthesis of steric hindered 2-amino-2′-ketonyl biaryls was reported. The reaction featured an acid-mediated azidation/ring-expansion/hydrolysis cascade, which formally realized t

Synthesis of phenanthridines by I2-mediated sp3C-H amination

An I2-mediated synthesis of phenanthridinesviaintramolecular sp3C-H amination of readily accessible aniline precursors is reported. The present synthetic process is straightforward and applicable to a broad variety of unprotected ani

Synthesis of phenanthridines through iodine-supported intramolecular C-H amination and oxidation under visible light

Herein, we report a metal-free and step-economic synthesis of phenanthridines from 2-biarylmethanamines under mild conditions. The reaction involves iodine-supported intramolecular C-H amination and oxidation of 5,6-dihydrophenanthridine under air and benign visible light. The mechanism study reveals that visible light plays a key role in both these steps.

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.

Introduction of Heteroaromatic Bases onto Cycloalkanes with BPO

Heteroaromatic bases, such as lepidine, phenanthridine, isoquinoline, etc., were treated with cycloalkanes, such as cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc., under warming conditions with benzoyl peroxide (BPO) to form heteroaromatic bases bearing cycloalkyl groups in good yields. Here, the inert C(sp3)-H bond of cycloalkanes could be functionalized to C(sp3)-heteroaromatic bases via an oxidative radical reaction pathway under transition-metal-free conditions.