94191-66-9

Upstream product

• 7154-66-7 2-bromobenzoic acid chloride 
• 100-61-8 N-methylaniline 
• 88-65-3 2-bromobenzoic-acid 
• 201230-82-2 carbon monoxide 
• 1295605-37-6 1-(2-bromophenyl)-3-methyl-3-phenyltriazene 
• 62-53-3 aniline 
• 10282-57-2 2-bromobenzanilide 
• 74-88-4 methyl iodide 
• 108-86-1 bromobenzene 

Downstream Products

• 65201-98-1 5-methylphenanthridinium chloride 
• 37395-60-1 2-bromo-5-methylphenanthridin-6(5H)-one 

Relevant academic research and scientific papers

Phenanthrapyridones derivatives, synthetic method thereof and electronic device containing phenanthrapyridones derivatives (by machine translation)

The phenanthrapyridones derivatives of, the present invention can be used for the synthesis of the phenanthones derivatives of the present invention. as the, electron blocking layers (1) or: electron ,L1 transport L2 layers of the electron blocking, layer

Palladium-Catalyzed Carbonylative Synthesis of Amides from Aryltriazenes under Additive-Free Conditions

An interesting palladium-catalyzed carbonylative synthesis of amides from aryltriazenes was developed. By using Pd(MeCN2)Cl2 as the catalyst precursor under CO pressure through a N2 extrusion/CO insertion sequence, a broad range of aryltriazenes were transformed into the corresponding amides in good yields with excellent functional group tolerance. Remarkably, no additives such as acids or phosphine ligands were required.

Synthesis and antibacterial activity of 5-methylphenanthridium derivatives as FtsZ inhibitors

5-Methylphenanthridium derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity and cell division inhibitory activity against various Gram-positive and -negative bacteria. Among them, compounds 5A2, 5B1, 5B2, 5B3, 5C1 and 5C2 displayed the best on-target antibacterial activity with an MIC value of 4?μg/mL against B. subtilis ATCC9372 and S. pyogenes PS, showing over 2-fold better activity than sanguinarine. The SARs showed that the 5-methylphenanthridium derivatives with the alkyl side chains at the 2-postion, especially the straight alkyl side chains exerted better on-target antibacterial activity.

Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KO: T Bu promoted intramolecular C-H arylation

A simple, efficient, rapid and transition metal-free methodology has been developed by utilizing vasicine (a natural product), as a catalyst for the synthesis of phenanthridinones and dihydrophenanthridines. The reaction proceeds through intramolecular C-H arylation with aryl halides in the presence of KOtBu as a base under microwave irradiation in sulfolane as a solvent. The reaction proceeds well with various aryl iodides, bromides and more remarkably with less reactive aryl chlorides for 15 minutes, providing the corresponding products in 45-90% yields.

A further decrease in the catalyst loading for the palladium-catalyzed direct intramolecular arylation of amides and sulfonamides

The direct arylation of N-substituted o-bromobenzanilides and benzenesulfonamides via C-H bond functionalization has been developed using very low catalyst loadings. This novel cost-effective and more sustainable method relies on a PCN-type palladium pincer complex as a highly active palladium source, providing a general and efficient access to phenanthridinones, biaryl sultams and related heterocyclic systems. The beneficial effect of water as cosolvent has been observed in this process, which is not seriously influenced by electronic effects at the arene moieties or sterically demanding substituents at the amide or sulfonamide nitrogen. In addition, a number of experiments (kinetic plot, poisoning assays, TEM, ESI) have been performed in order to understand the role of the employed palladium complex in this reaction.

Direct arylation under catalysis of an oxime-derived palladacycle: Search for a phosphane-free method

A phosphane-free method for the direct arylation of benzothiazole by employing oxime-derived palladacycle 1 as a catalyst was developed. The new catalyst system can be used for 2-arylations by using aryl bromides and iodides. In addition, this method is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well aschloroamides, to achieve a rapid synthesis of benzo[c]phenanthridine alkaloids. Direct arylation reactions under catalysis of an oxime-derived palladacycle were investigated. This phosphane-free method is applicable for the 2-arylation of benzothiazole and is especially suitable for the intramolecular direct coupling of bromo-and iodoamides, as well as chloroamides, to achieve rapid synthesis of benzo[c]phenanthridine alkaloids. Copyright

Ultrasound-promoted intramolecular direct arylation in a capillary flow microreactor

An intramolecular direct arylation of various aryl bromides was performed using ultrasonic irradiation and a continuous flow capillary microreactor. The present procedure provided a higher functional group tolerance, ligand-free, milder reaction condition

Investigation of the mechanism of C(sp3)-H bond cleavage in Pd(0)-catalyzed intramolecular alkane arylation adjacent to amides and sulfonamides

The reactivity of C(sp3)-H bonds adjacent to a nitrogen atom can be tuned to allow intramolecular alkane arylation under Pd(0) catalysis. Diminishing the Lewis basicity of the nitrogen lone pair is crucial for this catalytic activity. A range of N-methylamides and sulfonamides react exclusively at primary C(sp3)-H bonds to afford the products of alkane arylation in good yields. The isolation of a Pd(II) reaction intermediate has enabled an evaluation of the reaction mechanism with a focus on the role of the bases in the C(sp3)-H bond cleaving step. The results of these stoichiometric studies, together with kinetic isotope effect experiments, provide rare experimental support for a concerted metalation-deprotonation (CMD) transition state, which has previously been proposed in alkane C(sp3)-H arylation. Moreover, DFT calculations have uncovered the additional role of the pivalate additive as a promoter of phosphine dissociation from the Pd(II) intermediate, enabling the CMD transition state. Finally, kinetic studies were performed, revealing the reaction rate expression and its relationship with the concentration of pivalate.

Oxidation during reductive cyclisations using Bu3SnH

Reductive cyclisations using Bu3SnH include an "oxidation" step if the removal of an acidic proton from the intermediate cyclised radical, by Bu3SnH acting as a base, is favourable. A "pseudo" SRN1 mechanism is proposed.

PALLADIUM-CATALYSED CYCLISATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION

Cyclodehydrohalogenation mediated by various palladium catalysts and solvents with different bases (the most generally satisfactory system being palladium(II) acetate in NN-dimethylacetamide (DMA) with sodium carbonate as base) has been examined as a route to some heterocyclic systems.Whereas dehydrogenative cyclisation processes require stoichiometric amounts of palladium(II) reagent, the present procedure involves only catalytic amounts (0.1 molar proportion, or less), of palladium compound.The preparation of dibenzofuran, carbazole, fluorenone, 6H-dibenzothiazine-5,5-dioxide, 6H-dibenzopyran and benzofuranopyridine derivatives is described.The cyclisation of 3-benzamido-2-chloropyridine to 6-hydroxybenzonaphthiridine illustrates the regiospecificity of the process.