10604-22-5

Usage

InChI:InChI=1/C14H10N2/c1-2-6-11(7-3-1)14-10-12-8-4-5-9-13(12)15-16-14/h1-10H

Upstream product

• 7624-95-5 3-phenylcinnolin-4(1H)-one 
• 2835-06-5 phenylglycin 
• 552-89-6 2-nitro-benzaldehyde 
• 59105-14-5 1,2-diphenyl-ethanone acetylhydrazone 
• 23666-98-0 2-(2-(dimethylamino)phenyl)-1-phenylethanone 
• 3826-47-9 2-(2-fluorophenyl)-1-phenylethan-1-one 
• 27356-33-8 2-(2-methoxyphenyl)-1-phenylethan-1-one 
• 16897-97-5 2-(2-bromophenyl)-1-phenyl-1-ethanone 
• 57479-60-4 1-phenyl-2-(2-chlorophenyl)ethanone 
• 451-40-1 phenyl benzyl ketone 
• 4636-16-2 iodoacetophenone 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 724-15-2 4-hydroxy-3-phenylcinnoline 

Relevant academic research and scientific papers

N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights

A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2H-indazole synthesis, its reactivity was modulated for indazolone formation.

Cnoline compound and preparation method thereof

According to the method, o-nitrobenzaldehyde compounds and amino acid compounds which are low in price and easy to obtain are used as starting raw materials for reaction, activated carbon supported palladium is used as a catalyst for reaction, and a series of subsequent processes such as nucleophilic addition, proton transfer, cyclization, dehydration and reduction are initiated by catalyzing amino acid decarboxylation through palladium, thus, a cinnoline target product is constructed. The method presents a wide substrate range, has the advantages of mild reaction conditions, simplicity in operation and the like, and can effectively construct different substituted cinnoline compounds.

Copper-Catalyzed Aerobic Annulation of Hydrazones: Direct Access to Cinnolines

A novel method was developed for the construction of biologically active poly-substituted cinnolines from easily accessible hydrazones in good to excellent yields. A simple copper catalyst could efficiently promote C?N bond formation through selective C?H functionalization and dehydrogenative amination. Furthermore, the inert C?Heteroatom (O/F/N) bonds are susceptible to cleavage in high selectivity in the newly developed aerobic annulation, in preference to the alternative C?H bond, which is left intact. (Figure presented.).

Multicomponent Coupling Cyclization Access to Cinnolines via in Situ Generated Diazene with Arynes, and α-Bromo Ketones

A transition-metal-free multicomponent coupling cyclization reaction was explored involving arynes, tosylhydrazine, and α-bromo ketones. The reaction proceeds via a formal [2 + 2 + 2] cycloaddition, giving access to cinnoline derivatives in moderate yields under mild conditions. Three chemical bonds were formed-two C-N bonds and one C-C bond-in a single step.

Rhodium(III)-catalyzed cyclative capture approach to diverse 1-aminoindoline derivatives at room temperature

A RhIII-catalyzed C-H activation/cyclative capture approach, involving a nucleophilic addition of C(sp3)-Rh species to polarized double bonds is reported. This constitutes the first intermolecular catalytic method to directly access 1-aminoindolines with a broad substituent scope under mild conditions.

The effects of different solvents and excitation wavelength on the photophysical properties of two novel Ir(III) complexes based on phenylcinnoline ligand

Two novel cyclometalated iridium(III) complexes, Ir(pcl)2(pic) and Ir(pcl)2(fpic) (pcl: 3-phenylcinnoline, pic: picolinic acid, fpic: 5-fluoro-2-picolinic acid) were synthesized and characterized by FTIR, 1H NMR spectroscopy, UV-vis, PL, and MALDI-TOF. These two Ir-complexes geometry were predicted using the Sparkle/PM6 model and suggested to a chemical environment of very low symmetry around the Ir ions (C 1). The PL spectrum of Ir(pcl)2(pic) and Ir(pcl) 2(fpic) indicated that these complex belonged to red light emission, and maximum emission wavelength located at 647 and 641 nm, respectively. Most importantly, the effects of different solvents on their photoluminescent properties were detailed investigated. The results indicated that the polarity of solvent played an important role for their emission spectra. With introducing fluoro group to the pyridyl ring, the maximum emission wavelength of Ir(pcl)2(fpic) was blue shifted about 6 nm, and the quantum yield was slightly higher than that of Ir(pcl)2(pic). In addition, the thermal properties of these two Ir-complexes were measured by TGA, and results indicated that they had relative good thermal properties. [Figure not available: see fulltext.]

A general method to diverse cinnolines and cinnolinium salts

Rhodium catalysis: A highly efficient and general method has been established to prepare cinnolines, cinnolinium salts, and polycyclic cinnolinium salts through the rhodium(III)-catalyzed oxidative C-H activation/cyclization of azo compounds with alkynes (see scheme). Key features of this methodology include the unprecedented capacity to create both cinnoline and cinnolinium frameworks. Copyright

Copper-catalyzed aerobic dehydrogenative cyclization of N-methyl-N-phenylhydrazones: Synthesis of cinnolines

O2 leading the way: The title reaction proceeds through an oxidation/cyclization sequence, thus representing the first copper-catalyzed coupling reaction of hydrazones through a C sp 3-H bond functionalization process (see scheme; DMF=N,N'-dimethylformamide, Py=pyridine). The method provides an environmentally friendly and atom-efficient approach to biologically active cinnoline derivatives. Copyright

A Novel Approach to Synthesis of the Cinnoline Ring System via Organoiron(Cyclopentadienyl) Complexes

An efficient synthesis of 3-mono or 3,4-disubstituted cinnolines from (o-dichlorobenzene)(cyclopentadienyl)iron hexafluorophosphate in three or four steps has been achieved. o-Chlorophenyl-alkyl or alkylaryl ketone complexes obtained from the o-dichlorobe

Synthesis and Reactions of 4,6,7,8-Tetrahydro-5(1H)-cinnolinones

Phenacyldimedone, acetonyldimedone and analogues of general structure 1 undergo reaction with hydrazine, alkylhydrazine and phenyl- and 4-nitrophenyl-hydrazines to form 4,6,7,8-tetrahydro-5(1H)-cinnolinones (2) while 1b and 2,4-dinitrophenylhydrazine affo