4733-21-5

Usage

InChI:InChI=1/C24H18N4/c25-19-15-24-22(16-21(19)26-17-9-3-1-4-10-17)27-20-13-7-8-14-23(20)28(24)18-11-5-2-6-12-18/h1-16,25-26H/b25-19+

Upstream product

• 534-85-0 N-phenyl-1,2-benzenediamine 
• 4607-70-9 phenosafranin 
• 62-53-3 aniline 
• 7664-93-9 sulfuric acid 

Downstream Products

• 69272-46-4 5,12-diphenyl-5,12-dihydroquinoxalino[2,3-b]phenazine 
• 58059-12-4 2-phenylamino-5-phenyl-3-phenazinone 
• 106691-10-5 1,4-dichloro-3-(2,4-dichloroanilino)-2,10-dihydro-2-imino-10-phenylphenazine 
• 106690-89-5 1,4-dibromo-3-(2,4-dibromoanilino)-2,10-dihydro-2-imino-10-phenylphenazine 
• 124116-86-5 2-(2-methyl-1,5-diphenyl-2,5-dihydro-1H-imidazo[4,5-b]phenazin-2-yl)-ethanol 
• 106691-05-8 2-cyclohexylimino-3-(2,4-dibromoanilino)-2,10-dihydro-10-phenylphenazine 
• 106691-04-7 1-bromo-3-(2,4-dibromoanilino)-2,10-dihydro-2-imino-10-phenylphenazine 

Relevant academic research and scientific papers

A Sustainable Synthesis of Asymmetric Phenazines and Phenoxazinones Mediated by CotA-Laccase

An efficient and sustainable one-step procedure for the synthesis of new asymmetric phenazines and phenoxazinones from commercially available ortho-substituted diamines and ortho-substituted hydroxyamines is reported. In this study we have expanded the substrate scope of CotA-laccase-catalyzed aerobic oxidations through the use of aromatic amines presenting variable functional groups, including N-substitution, contributing to the rational synthesis of different heterocyclic scaffolds. The transformations proceed smoothly through a cascade of oxidative reactions to the benzoquinonediimine intermediates followed by nucleophilic addition, intramolecular cyclization and aromatization, all performed in mild conditions. (Figure presented.).

Visible-light-mediated synthesis of substituted phenazine and phenoxazinone using eosin y as a photoredox catalyst

This paper describes an efficient, sustainable, one-step procedure for synthesizing substituted phenazines and phenoxazinones from commercially available ortho-substituted aromatic amines with very good yield (≥80%) in water. The procedure uses eosin Y (EY) as a photoredox catalyst at room temperature (RT). The highly reactive o-quinone-diimine or o-quinone-imine intermediate was characterized by the HR-MS technique.

TEMPO-catalyzed electrochemical dehydrogenative cyclocondensation of: O -aminophenols: Synthesis of aminophenoxazinones as antiproliferative agents

The aminophenoxazinone core is widely prevalent in natural products, dyes and pharmaceutical molecules. We report here a TEMPO-catalyzed electrosynthetic method allowing the dehydrogenative cyclocondensation of o-aminophenols. This mild and sustainable method proceeds in the absence of stoichiometric oxidants and uses an easily available organo-electrocatalyst to access pharmaceutically valuable 2-aminophenoxazinones. Mechanistic studies indicate that the electrochemically generated TEMPO+ enables the oxidative radical homo-dimerization of o-aminophenols. The application of electrosynthesis provides an approach for the synthesis of pseudo-aminophenoxazinone alkaloids with improved structural diversification and bioactivities. This journal is

Optimization of the clofazimine structure leads to a highly water-soluble C3-aminopyridinyl riminophenazine endowed with improved anti-Wnt and anti-cancer activity in vitro and in vivo

Triple-negative breast cancer (TNBC) is a cancer subtype critically dependent upon excessive activation of Wnt pathway. The anti-mycobacterial drug clofazimine is an efficient inhibitor of canonical Wnt signaling in TNBC, reducing tumor cell proliferation

Waste minimized synthesis of pharmaceutically active compounds: Via heterogeneous manganese catalysed C-H oxidation in flow

Herein, we present our results on the development of a continuous flow protocol enabling the waste minimised synthesis of relevant pharmaceuticals and natural compounds. Heterogeneous manganese catalytic systems have been used in combination with molecular oxygen to promote the C-H oxidative coupling of 2-aminophenols, benzenetriols and o-phenylenediamines to access a variety of 2-aminophenoxazin-3-ones (2a-i) and related diaminophenazines (2j-k) and purpurogallin (2l) with minimal metal contamination. Making use of safe and green cyclopentyl methyl ether (CPME), this methodology allowed a fast synthesis of fully decorated molecular entities, preserving the stability of the heterogeneous catalyst which showed minimal metal leaching, with minimal waste production (low E-factor).