42606-35-9

Upstream product

• 613-51-4 7-nitroquinoline 
• 74-89-5 methylamine 
• 33757-48-1 N-quinolin-8-yl-benzamide 
• 578-66-5 8-amino quinoline 
• 30450-62-5 7-nitro-1,2,3,4-tetrahydro-quinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 99-09-2 3-nitro-aniline 

Downstream Products

• 78105-42-7 7,8-diaminoquinoline 

Relevant academic research and scientific papers

Regioselective C-7 Nitration of 8-Aminoquinoline Amides Using tert-Butyl Nitrite

Regioselective C-7 nitration of 8-aminoquinoline amide has been achieved using tert-butyl nitrite under metal-free conditions at ambient temperature. The protocol is applicable to various aryl, heteroaryl as well as aliphatic carboxamides, and exhibits high functional group compatibility. The present method provides selective mononitrated quinoline derivatives. Experimental results suggest that the reaction likely proceeds through a radical pathway. (Figure presented.).

A First Example of Cobalt-Catalyzed Remote C H Functionalization of 8-Aminoquinolines Operating through a Single Electron Transfer Mechanism

The development of new C H functionalization protocols based on inexpensive cobalt catalysts is currently attracting significant interest. Functionalized 8-aminoquinoline compounds are high-potential building blocks in organic chemistry and pharmaceutical compounds and new facile routes for their preparation would be highly valuable. Recently, copper has been applied as catalyst for the functionalization of 8-aminoquinoline compounds and found to operate through a single electron transfer (SET) mechanism, although requiring elevated reaction temperatures. Herein, we described the first example of a cobalt-catalyzed remote C H functionalization of 8-aminoquinoline compounds operating through a SET mechanism, exemplified using a practical and mild nitration protocol. The reaction uses inexpensive cobalt nitrate hexahydrate [Co(NO3)2?6 H2O] as catalyst and tert-butyl nitrite (TBN) as nitro source. This methodology offers the basis for the facile preparation of many new functionalized 8-aminoquinoline derivatives. (Figure presented.).

Controlling ground and excited state properties through ligand changes in ruthenium polypyridyl complexes

The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)2(N-N)]2+ (bpy = 2,2-bipyridine; N-N is a bidentate polypyridyl ligand). In this series, the nature of the N-N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the φ* orbitals on the N-N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)32+ (λmax = 449 nm) with the lowest energy MLCT absorption appearing at λmax = 564 nm. Emission energies decrease from λmax = 650 nm to 885 nm across the series. One-mode Franck-Condon analysis of room-temperature emission spectra are used to calculate key excited state properties, including excited state redox potentials. The impacts of ligand changes on visible light absorption, excited state reduction potentials, and Ru3+/2+ potentials are assessed in the context of preparing low energy light absorbers for application in dye-sensitized photoelectrosynthesis cells.

Vicarious nucleophilic amination of nitroquinolines by 1,1,1- trimethylhydrazinium iodide

(Chemical Equation Presented) The amination of 3-, 5-, 6-, 7- and 8-nitroquinoline via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK in DMSO was studied. The amination occurs regioselectively giving ortho or ortho and para isomers relative to the nitro group with a high yield (95-86%). 2-Nitroquinoline does not undergo vicarious amination but displacement of the labile nitro group by an amino group occurs and then transformation to an imine compound and hydrolysis gives 2(1H)-quinolinone.

Vicarious nucleophilic amination of Nitroquinolines with 4-amino-1,2,4-triazole

3-, 5-. 6-, 7- and 8-Nitroquinolines react with 4-amino-l,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-zh]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(l,2,4-triazol-4-yl)amine in these conditions.

Oxidative Methylamination of Nitroquinolines

3-, 5-, 6-, 7- and 8-nitroquinoline as well as 5,7- and 6,8-dinitroquinoline are methylaminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono- and bis(methylamino)-substituted compounds. 2-Nitroquinoline is aminated with LMA/PP to 2-(methylamino)quinoline.The intermediate methylamino ?-adducts of 3-nitro- and 5,7- and 6,8-dinitroquinoline are detected by 1H-NMR spectroscopy.Quantum chemical calculations for the mononitroquinolines suggest that the experimentally observed regioselectivity of the methylamination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents. Key Words: Methylaminations / ?-Adducts, methylamino / Calculations, FMO / Quinolines / Aminations

Frontier Orbital Interactions in the Regioselectivity of the Amination of Nitroquinolines by Liquid Ammonia/Potassium Permanganate

5-Nitro-,6-nitro-,7-nitro-,8-nitro-,and 2-nitroquinoline and 5,7-dinitro and 6,8-dinitroquinoline were aminated in a liquid ammonia solution of potassium permanganate. 8-Nitro and 2-nitroquinoline were found to be unreactive.The intermediary ?-adducts,formed between 5,7-dinitro- and 6,8-dinitroquinoline and liquid ammonia, could be detected by 1H NMR spectroscopy.FMO calculations nicely confirm the experimentally observed regioselectivity of the amination.