195-29-9

Upstream product

• 19730-94-0 1,2,3,4-tetrahydro-benzo[a]phenanthridine 
• 101600-52-6 N-(1-phenyl-[2]naphthyl)-formamide 
• 142598-69-4 2-(naphthalene-1-yl)benzaldehyde 
• 28322-50-1 2-diazo-1-phenyl-2-(phenylsulfonyl)ethan-1-one 
• 29601-75-0 1-phenyl-2-aminonaphthalene 
• 13922-41-3 1-Naphthylboronic acid 
• 6630-33-7 ortho-bromobenzaldehyde 

Relevant academic research and scientific papers

Electrochemical Decarboxylative Cyclization of α-Amino-Oxy Acids to Access Phenanthridine Derivatives

Phenanthridines are a class of useful heterocycles in the field of drug development. In this work, a method via electrochemical decarboxylative cyclization of α-amino-oxy acids to access phenanthridine derivatives was developed. This reaction proceeded th

Metal-free tandem carbene N-H insertions and C-C bond cleavages

A metal-free C-H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C-C cleavage. Compared to the simple N-H insertion manipulation of diazo, this method elegantly accomplishes a tandem N-H insertion/SEAr/C-C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids. This journal is

Visible-light-promoted and one-pot synthesis of phenanthridines and quinolines from aldehydes and o -Acyl hydroxylamine

A one-pot synthesis of phenanthridines and quinolines from commercially available or easily prepared aldehydes has been reported. O-(4-Cyanobenzoyl)hydroxylamine was utilized as the nitrogen source to generate O-acyl oximes in situ with aldehydes catalyzed by Bronsted acid. O-Acyl oximes were then subjected to visible light photoredox catalyzed cyclization via iminyl radicals to furnish aza-arenes. A variety of phenanthridines and quinolines have been prepared assisted by Bronsted acid and photocatalyst under visible light at room temperature with satisfactory yields.

Electron-transfer-mediated synthesis of phenanthridines by intramolecular arylation of anions from n-(ortho-Halobenzyl)arylamines: regiochemical and mechanistic analysis

The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(orrAo-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of orthohalobenzylchlorides with different arylamines. The reaction of the anions of a diverse set N-(orthohalobenzyl)arylamines was studied, and the methodology was extended to the synthesis of trispheridine, a natural product, in very good yield, In order to explain the regiochemical outcome of these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.

Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via SRN1 reactions

The photostimulated reaction of N-(2-halo-benzyl)aryl amines with t-BuOK in liquid ammonia affords fused azaheterocycles by the SRN1 mechanism. The starting materials are easily obtained by the reaction of 2-halo-benzyl chloride and aromatic amines to prepare the secondary amines. Through this approach, phenanthridine (90%), 4-phenylphenanthridine (87%), benzo[a]phenanthridine (98%), and benzo[c]phenanthridine (84%) were synthesized.