397-57-9

Upstream product

• 2876-23-5 phenazin-2-amine 
• 372-19-0 meta-fluoroaniline 
• 98-95-3 nitrobenzene 
• 1621867-47-7 8-fluoro-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine 
• 1621867-48-8 7-fluoro-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine 
• 586-96-9 Nitrosobenzene 
• 1195-45-5 para-fluorophenyl isocyanate 
• 62-53-3 aniline 
• 95-54-5 1,2-diamino-benzene 
• 144025-03-6 2,4-difluorophenylboronic acid 
• 371-40-4 4-fluoroaniline 
• 88-73-3 2-Chloronitrobenzene 
• 322-78-1 2-(4’-fluoroanilido)nitrobenzene 

Relevant academic research and scientific papers

An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine

Herein, Ag(I)-promoted regioselective intramolecular radical nucleophilic addition/rearrangement of 2-aryl diazaboroles has been accomplished for the first time to construct phenazine structures. This protocol is an umpolung strategy based on the classical electrophilic mechanism, and therefore, a reversed regioselectivity was observed, which provides an opportunity to prepare sterically hindered phenazines. The resulting thermally activated delayed fluorescence (TADF) materials based on phenazine exhibit emission bands from green to red with high quantum yields and moderate fluorescence lifetimes as solid films.

The silver-mediated annulation of arylcarbamic acids and nitrosoarenes toward phenazines

A silver-mediated annulation between arylcarbamic acids and nitrosoarenes was developed, leading to phenazines in moderate to good yields with complexity and diversity. This procedure proceeded with the sequential ortho[sbnd] C[sbnd]H functionalization of arylcarbamic acids, insertion to nitroso group and decarboxylative annulation.

Preparation method of phenazine compound

To the method, a phenazine compound is prepared through continuous ortho C-H functionalization, nitroso insertion and decarboxylation processes of aryl carbamic acid, wherein a carboxyl amino group serves as a trace-free positioning group.

Reactivity and substituent effects in the cyclization of N-aryl-2-nitrosoanilines to phenazines

Reactivity of variously substituted N-aryl-2-nitrosoanilines in the reaction of cyclization leading to phenazine derivatives, carried out in the presence of N,O-bis(trimethylsilyl)acetamide (BSA), was estimated on the base of the observed reaction times. A strong opposite effect of substituents located at position para to the nitroso group and those located para to the amino group in the side ring was observed. Mechanistic explanation, based on the electronic properties of the substituents and their mesomeric effects, was presented. The usefulness of the obtained data for the designed syntheses of phenazines was exposed.

Transition-metal-free tandem oxidative removal of benzylic methylene group by C-C and C-N bond cleavage followed by intramolecular new aryl C-N bond formation under radical conditions

A novel tandem oxidative conversion of 10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines to phenazines has been achieved under transition-metal-free, mild conditions using K2S2O8 or DDQ as the oxidizing agent. The transformation proceeds through oxidative removal of a benzylic methylene group by C-C and C-N bond cleavage followed by a new aryl C-N bond formation under radical conditions.