39217-93-1

Usage

Uses

Used in Pharmaceutical Synthesis:
8-NITRO-1,2,3,4-TETRAHYDROQUINOLINE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows for the development of new drugs and therapies with potential applications in the treatment of various diseases and conditions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 8-NITRO-1,2,3,4-TETRAHYDROQUINOLINE is employed as a building block for the design and synthesis of novel compounds with potential therapeutic properties. Its antioxidant and anti-inflammatory activities make it a valuable component in the development of drugs targeting oxidative stress and inflammation-related disorders.
Used in Organic Synthesis:
8-NITRO-1,2,3,4-TETRAHYDROQUINOLINE serves as an important intermediate in organic synthesis, enabling the creation of a wide range of chemical compounds with diverse applications. Its versatility in undergoing various chemical reactions allows for the exploration of new synthetic pathways and the discovery of innovative molecules with potential uses in various industries.
Used in Drug Development:
The potential applications of 8-NITRO-1,2,3,4-TETRAHYDROQUINOLINE in drug development are vast, as it can be used to create new therapeutic agents with improved efficacy and reduced side effects. Further research and studies on 8-NITRO-1,2,3,4-TETRAHYDROQUINOLINE may lead to its incorporation in the pharmaceutical industry, contributing to the advancement of medicine and healthcare.

Upstream product

• 607-35-2 8-nitroquinoline 
• 1290608-24-0 N-acetyl-8-nitro-1,2,3,4-tetrahydroquinoline 
• 4169-19-1 1-acetyl-1,2,3,4-tetrahydroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 767-92-0 decahydroquinoline 

Downstream Products

• 607-35-2 8-nitroquinoline 

Relevant academic research and scientific papers

NHC-Palladium(II) Mononuclear and Binuclear Complexes Containing Phenylene-Bridged Bis(thione) Ligands: Synthesis, Characterization, and Catalytic Activities

A series of mono- and binuclear Pd(II) complexes with N-heterocyclic carbene (NHC) and phenylene-bridged bis(thione) (SCS) ligands were prepared and characterized by 1H and 13C NMR spectroscopy, IR, and mass spectrometry. The molecular structures of 1b, 2a, and 3b have been determined by the single-crystal X-ray diffraction method. The catalytic activities of the synthesized palladium complexes in the regioselective reduction of quinolines to the corresponding 1,2,3,4-tetrahydroquinolines were thoroughly investigated with ammonia-borane under mild reaction conditions. It is observed that the activities of the binuclear Pd(NHC) complexes were higher than those of the corresponding mononuclear complexes under the same conditions.

Encapsulating Cobalt into N-Doping Hollow Frameworks for Efficient Cascade Catalysis

The development of nonprecious catalysts for hydrogenation of organic molecules is of great importance in heterogeneous catalysis. Herein, we report a series of N-doped hollow carbon frameworks encompassing cobalt nanoparticles (denoted as Co@NHF-900) constructed as a new kind of reusable catalyst for this purpose by pyrolysis of ZIF-8@Co-dopamine under Ar atmospheres. Notably, the framework of ZIF-8 is essential for efficient catalyst by providing a carbon framework to support Co-dopamine. The experimental results reveal that the ZIF-8 renders a large hollow place within the catalysts, allowing the enrichment of the substrate and windows of the hollow structure and the ease of mass transfer of products during the reaction. All of the virtues made Co@NHF-900 a good candidate for hydrogenation of quinolines with high activity (TOF value of 119 h-1, which is several times than that of akin catalysts) and chemoselectivity.

Cu Nanoclusters Anchored on the Metal-Organic Framework for the Hydrolysis of Ammonia Borane and the Reduction of Quinolines

Free-access active sites created and the interaction regulated between them and substrates during the heterogeneous catalysis process are crucial, which remain a great challenge. In this work, in suit reduced to afford naked Cu nanoparticles (NPs) have been anchored on the metal-organic framework (MOF), NH2-MOF, to form Cu-NH2-MOF. The strategy can precisely control the Cu NP formation with small size and uniform distribution. The Cu NP properties and MOF advantages have been integrated to create a great catalyst with multiple functions and have resulted in improving the recyclability and superb catalytic activity for the one-pot reduction of heterocycle reactions under mild conditions. The experimental and theoretical calculation results show that the superior performance should be attributed to the framework of NH2-MOF that provides large caves for substrate enrichment and the stabilization of Cu sites by the -NH2 group.

Iodine catalyzed reduction of quinolines under mild reaction conditions

A reduction of quinolines to synthetically versatile tetrahydroquinoline molecules with I2 and HBpin is described. In the presence of iodine (20 mol%) as a catalyst, reduction of quinolines and other N-heteroarenes proceeded readily with hydroboranes as the reducing reagents. The broad functional-group tolerance, good yields and mild reaction conditions imply high practical utility.

High efficient iron-catalyzed transfer hydrogenation of quinolines with Hantzsch ester as hydrogen source under mild conditions

A highly efficient transfer hydrogenation of quinolines with Hantzsch ester as hydrogen source in the presence of 1 mol% Fe(OTf)2 under mild conditions has been developed. A series of substituted 1,2,3,4-tetrahydroquinoline derivatives were afforded in excellent yields with good functional group tolerance.

Synthesis of 6-nitro-1,2,3,4-tetrahydroquinoline: An experimental and theoretical study of regioselective nitration

A revision of the literature on the nitration of tetrahydroquinolines yielded a number of inconsistencies. Thus, we have carried out a thorough study on the nitration of tetrahydroquinoline and several of its N-protected derivatives both experimentally and at theoretical level. Usually, nitration is carried out in acidic conditions and, thus, tetrahydroquinoline would be N-protonated; however, if the amino group is protected, the neutral system will be the one undergoing nitration. Different protecting groups have been explored varying, not only electronic and steric effects, but also deprotection conditions. Additionally, different reagents and reaction conditions have been investigated. From this study we have been able to achieve total regioselectivity for nitration at the 6-position. A very detailed NMR study has been carried out to unequivocally characterise the four nitro isomers. In parallel, a computational study has been performed that is in agreement with the experimental results obtained. With this purpose, all the σ complexes of the four nitro isomers neutral and N-protonated have been optimized both in gas and water condensed phases by using the B3LYP/6-31++G* level of computation. The selective nitration of tetrahydroquinoline was studied. N-Protecting groups presence or absence directs nitration at different positions. Regioselective nitration at 6-position was achieved. A DFT computational study of all nitro σ complexes was performed in gas and water phases, the results are consistent with the experiments. Copyright