21874-06-6

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Phenylcinnoline is used as a building block for the synthesis of various pharmaceuticals and organic compounds, leveraging its unique structure and properties to create new and effective medications.
Used in Drug Discovery and Medicinal Chemistry Research:
Due to its anti-inflammatory, anti-cancer, and anti-bacterial properties, 4-Phenylcinnoline serves as a valuable tool in drug discovery and medicinal chemistry research, aiding in the development of novel therapeutic agents.
Used in Biological Imaging and Studies:
4-Phenylcinnoline is utilized as a fluorescent probe in biological imaging and studies, enabling researchers to visualize and study biological processes and structures with enhanced clarity and precision.
Used in Anti-Inflammatory Applications:
4-Phenylcinnoline is employed for its anti-inflammatory properties, potentially contributing to the development of treatments for various inflammatory conditions.
Used in Anti-Cancer Applications:
Leveraging its anti-cancer properties, 4-Phenylcinnoline is used in the development of cancer treatments, targeting the inhibition and control of tumor growth.
Used in Anti-Bacterial Applications:
4-Phenylcinnoline is used for its anti-bacterial properties, playing a role in the creation of new antibiotics or treatments for bacterial infections.

Upstream product

• 64097-92-3 2-(1-phenylvinyl)aniline 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 412305-23-8 4-phenyl-1,2-dihydro-cinnoline 
• 64-17-5 ethanol 
• 5152-84-1 4-chlorocinnoline 
• 98-80-6 phenylboronic acid 
• 536-74-3 phenylacetylene 
• 62-53-3 aniline 
• 2364-50-3 isovaleranilide 
• 187463-09-8 (Z)-1-(2-bromovinyl)-2-chlorobenzene 
• 24009-93-6 diethyl dihydrocinnoline-1,2-dicarboxylate 
• 1393462-68-4 C₁₄H₁₅ClN₂O₄ 
• 1393462-69-5 diethyl 4-phenyldihydrocinnoline-1,2-dicarboxylate 

Downstream Products

• 1504-16-1 3-phenyl-1H-indole 
• 412305-23-8 4-phenyl-1,2-dihydro-cinnoline 
• 91330-47-1 5-phenyl-pyridazine-3,4-dicarboxylic acid 
• 26631-10-7 4-isopropylidene-1,1-dimethyl-7-phenyl-[1,3,4]oxadiazino[4,3-a]cinnolin-2-one 

Relevant academic research and scientific papers

Iridium-Catalyzed α-Selective Arylation of Styrenes by Dual C?H Functionalization

An IrI-system modified with a ferrocene derived bisphosphine ligand promotes α-selective arylation of styrenes by dual C?H functionalization. These studies offer a regioisomeric alternative to the Pd-catalyzed Fujiwara–Moritani reaction.

Tert -Butyl nitrite (TBN) as the N atom source for the synthesis of substituted cinnolines with 2-vinylanilines and a relevant mechanism was studied

A green method to synthesize cinnolines by 6π electrocyclic reaction with alkenyl amines and TBN has been developed. TBN plays a dual role both as a nitrogen atom source and an oxidant in this procedure. Relevant mechanism experiments reveal that the reaction proceeds through electrocyclic reaction and with diazo hydroxide as a key intermediate.

Pd-assisted cross-coupling reactions with 4-chlorocinnoline

A series of 4-ethynylcinnolines 3a-e was prepared by Sonogashira reaction of 4-chlorocinnoline (1) with appropriate alkynes. Moreover, Suzuki coupling of with boronic esters gave the corresponding 4-arylcinnolines 5a-c. Detailed NMR spectroscopic data including unambiguous chemical shift assignments of all 1H, 13C, and 15N resonances of the obtained cinnoline derivatives are reported.

Copper-catalyzed tandem C-N bond formation: An efficient annulative synthesis of functionalized cinnolines

Cinn-tillating synthesis: The combination of a readily available copper catalyst, a simple hydrazide nucleophile, and established difunctionalized building blocks provides a new, flexible route to an under-developed class of aromatic heterocycles, cinnolines (see scheme). Copyright

Dirhodium(II)-catalyzed intramolecular C-H amination of aryl azides

(Chemical Equation Presented) Azides to indoles: Dirhodium(II)-catalyzed decomposition of aryl azides was developed as a mild, functional group tolerant method for the synthesis of indoles (see scheme).

Aromatic Diazonium Salts, X. - A One-Pot Procedure for the Jacobson Synthesis of Indazole

Procedures are described for a one-pot synthesis of 1H-indazole and substituted indazoles 3 in good yield (Table 1) from o-toluidines 2, alkyl nitrite or nitrous oxides, potassium acetate, and acetic anhydride in benzene.The spectroscopic properties of substituted indazoles (Tables 2-4) are discussed. - 4-Phenylcinnoline (18) is prepared by the same procedure from o-(α-methylenebenzyl)aniline.