16573-51-6

Upstream product

• 1836-87-9 9-Benzylidene-9H-fluorene 
• 1620087-08-2 2-phenyl phenyl isonitrile 
• 108-88-3 toluene 
• 36322-03-9 9-benzyl-9-fluorenol 
• 5346-21-4 N-formyl-2-aminobiphenyl 
• 615-43-0 2-iodophenylamine 
• 2943-26-2 S-benzyl O-ethylxanthate 
• 3128-77-6 2-isocyanobiphenyl 
• 591-50-4 iodobenzene 
• 140-29-4 phenylacetonitrile 
• 14548-01-7 phenanthridine N-oxide 
• 78761-38-3 cinnamyl propionate 
• 103-50-4 dibenzyl ether 
• 103-82-2 phenylacetic acid 

Downstream Products

• 91871-07-7 phenanthridin-6-yl(phenyl)methanone 

Relevant academic research and scientific papers

Metal-Free Synthesis 6-Benzylphenanthridines via Radical Addition/Cyclization of 2-Isocyanobiphenyls

A simple and practical approach has been established for the synthesis of 6-benzylphenanthridines from benzylic hydrocarbons and 2-isocyanobiphenyls via C(sp 3)-H/C(sp 2)-H bond functionalization under metal-free condition. The reaction exhibits good functional group tolerance and delivers the target products in moderate to excellent yields. The preliminary mechanistic investigation revealed that a radical intermediate might be involved in this reaction.

Photocatalytic xanthate-based radical addition/cyclization reaction sequence toward 2-biphenyl isocyanides: Synthesis of 6-alkylated phenanthridines

A photocatalytic xanthate-based radical addition/cyclization reaction cascade toward 2-biphenylisocyanides is described as a practical and modular approach to 6-alkylated phenanthridines. The use of xanthates as radical precursors allowed the synthesis of diversely 6-substituted phenanthridines. Electrophilic radicals derived from nitriles, aromatic and aliphatic ketones, malonates, and amide derivatives, as well as radicals derived from phthalimidomethyl and benzylic derivatives were successfully introduced. The reaction proceeds under mild conditions without a stoichiometric amount of oxidant. Thirty novel phenanthridine scaffolds were synthesized with yields ranging from 24 to 76%.

Rapid synthesis of polysubstituted phenanthridines from simple aliphatic/aromatic nitriles and iodo arenes: Via Pd(ii) catalyzed domino C-C/C-C/C-N bond formation

An efficient and straightforward method has been developed for the synthesis of polysubstituted phenanthridines from simple aryl iodides and alkyl/aryl nitriles via the palladium-catalyzed nucleophilic addition of aryl iodides to nitriles followed by casc

Photocatalyzed ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage

A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon–carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.

Synthetic method of 6-benzyl phenanthridine compounds

The invention discloses a synthetic method of 6-benzyl phenanthridine compounds. A reaction equation is as follows: formula (shown in the description), wherein R represents hydrogen, fluorine, chlorine, methyl, methoxyl or a naphthalene ring. The synthetic method has the beneficial effects that (1) the operation of the preparation process is simple and convenient, and the post-treatment of obtained products is easy; (2) high temperature and high pressure conditions are not required, and reaction conditions are mild; (3) a catalyst is not required, and the synthetic cost is lowered; (4) functional groups of a reaction substrate are high in tolerance, and the substrate is wide in range and easy to prepare; (5) an oxidant is cheap, easily available and relatively economic; (6) the reaction is efficient and high in yield; and (7) the synthetic method is pollution-free and environment-friendly.

A radical addition/cyclization of diverse ethers to 2-isocyanobiaryls under mildly basic aqueous conditions

Mildly basic aqueous conditions facilitated the tert-butyl peroxybenzoate (TBPB) mediated dehydrogenative addition of a range of ethers, including acetals, to diverse substituted 2-isocyanobiaryls. Mechanistic studies suggest that this radical cascade is an example of base promoted homolytic aromatic substitution (BHAS).

Transition Metal-Free Oxidative Radical Decarboxylation/Cyclization for the Construction of 6-Alkyl/Aryl Phenanthridines

A radical cascade decarboxylation/cyclization of 2-isocyanobiphenyls with aliphatic carboxylic acids as well as aromatic carboxylic acids under the transition metal-free conditions was reported. This process, which included formation of two new C-C bonds and cleavage of C-COOH bonds, afforded a novel and environmentally friendly approach to producing 6-alkyl/aryl phenanthridines with moderate to good yields.

Metal-free nitrogenation of 2-acetylbiphenyls: Expeditious synthesis of phenanthridines

An intermolecular nitrogenation reaction toward the synthesis of phenanthridines has been developed. This metal-free protocol provides a novel nitrogen-incorporation transformation using azides as the nitrogen source. Phenanthridines, which are of great interest in pharmaceutical and medicinal chemistry, are synthesized efficiently in one step. Moreover, the byproducts derived from the Schmidt reaction are inhibited, which further demonstrated the high chemoselectivity of this transformation.

Preparation of Substituted Phenanthridines from the Coupling of Aryldiazonium Salts with Nitriles: A Metal Free Approach

A transition metal free approach for the synthesis of substituted phenanthridines from the coupling reaction of aryldiazonium tetrafluoroborates with nitriles has been developed. This operationally simple protocol proceeds through a substitution of aryldiazonium with nitriles followed by an intramolecular arylation to provide the corresponding phenanthridines in moderate to excellent yields. (Chemical Equation Presented).

Visible-light-promoted iminyl-radical formation from Acyl oximes: A unified approach to pyridines, quinolines, and phenanthridines

A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac-[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e- reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-light-induced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]phenanthridine alkaloids.