17104-70-0

Usage

InChI:InChI=1/C13H9NO/c15-14-9-3-5-11-8-7-10-4-1-2-6-12(10)13(11)14/h1-9H

Upstream product

• 230-27-3 7,8-benzoquinoline 
• 101327-84-8 1-nitronaphthalene-2-carboxaldehyde 

Downstream Products

• 5278-58-0 2-phenyl-benzo[H]quinoline 
• 230-27-3 7,8-benzoquinoline 
• 23981-06-8 benzoquinolin-1(2H)-one 
• 77464-47-2 2-phenyl-7,8-benzoquinoline N-oxide 
• 1336877-38-3 2-benzylbenzo[h]quinoline 
• 605-88-9 2-methylbenzo[h]quinoline 
• 1417437-48-9 2-cyclohexylbenzo[h]quinoline 1-oxide 

Relevant academic research and scientific papers

Electrochemical-Oxidation-Promoted Direct N-ortho-Selective Difluoromethylation of Heterocyclic N-Oxides

An efficient and green electrochemical N-ortho-selective difluoromethylation method of various quinoline and isoquinoline N-oxides has been developed. In this method, sodium difluoromethanesulfinate (HCF2SO2Na) was used as the source of the difluoromethyl moiety, and various N-ortho-selective difluoromethylation quinoline and isoquinoline N-oxides were obtained in good to excellent yields under a constant current. In addition, the reaction was easy to scale up and maintained a good yield. Preliminary mechanism studies suggested that the reaction undergoes a free-radical addition and hydrogen elimination pathway.

Copper/manganese oxide catalyzed regioselective amination of quinoline N-oxides: An example of synergistic cooperative catalysis

An atom economical and efficient protocol for C-2 amination of quinoline N-oxides using our synthesized recyclable heterogeneous Cu–MnO catalyst has been reported here. Direct C[sbnd]H aminations of heterocyclic N-oxides with secondary amine were carried out under base, and ligand-free conditions in good to excellent yields. The major advantage is that air is used as a sole oxidant and our catalyst is recycled several times.

Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions

A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.

Cu-Catalyzed carbamoylation: Versus amination of quinoline N -oxide with formamides

An efficient, direct carbamoylation and amination of quinoline N-oxides with formamides to access 2-carbamoyl and 2-amino quinolines has been developed through copper-catalyzed C-C and C-N bond formations via cross-dehydrogenative coupling reactions. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. Mechanistic studies suggest that the reaction is initiated by formamide radical or decarbonylative aminyl radical formation in the presence of TBHP, according to the different substituent on the N atom of formamide.

Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions

A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).

Simple and scalable electrochemical synthesis of 2,1-benzisoxazoles and quinoline: N -oxides

Cathodic reduction of the nitro moiety and subsequent intramolecular cyclization affords different substituted 2,1-benzisoxazoles and quinoline N-oxides. This methodology allows the synthesis of two different types of heterocycles from common simple starting materials, using electrons as a sole reagent for this transformation. The electrolysis can be conducted in a very simple undivided electrolysis cell under constant current conditions. This permits working on a larger scale compared to other electrochemical methodologies and represents a significant advantage.

Synthesis of heteroaromatic trifluoromethyl ethers with trifluoromethyl triflate as the source of the trifluoromethoxy group

A series of nitrogen-heterocycles have been transformed to the corresponding trifluoromethyl or higher perfluoroalkyl ethers by reaction of the corresponding N-oxides with trifluoromethyl or higher perfluoroalkyl triflate. Trifluoromethyl triflate, which has generally been used as a precursor to [OCF3]?, is used here as a bifunctional reagent to render the heteroarene more electrophilic and to deliver the trifluoromethoxy group. This reagent was easily prepared on a large scale (>100 grams) and is stable in either pure form or as a stock solution. Applications and limitations of this method are reported.

Transition-Metal-Free Regioselective Alkylation of Quinoline N-Oxides via Oxidative Alkyl Migration and C?C Bond Cleavage of tert-/sec-Alcohols

An unprecedented C2-alkylation of quinoline N-oxide derivatives via C?C bond activation of tert- and sec-alkyl alcohol is described using hypervalent iodine (III) reagent PhI(OAc)2 (PIDA). This regioselective alkylation using mild hypervalent iodine reagents is more practical, operationally simple and transition metal free. The reaction proceeds efficiently with a broad range of substrates including quinoline, isoquinoline, and pyridine N-oxides using a variety of tert-/sec- alcohols. From experimental outcome, we also propose a rationalized mechanism, mediated by PIDA. (Figure presented.).

Dehydrogenative etherification homocoupling of heterocyclic N-oxides

A novel approach was developed for the dehydrogenative etherification homocoupling of heterocyclic N-oxides in the presence of silver oxide and PyBroP. Various substrates were well tolerated and the desired products were obtained in moderate to good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and good regioselectivity.

Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles

A net redox-neutral method for the decarboxylative alkylation of heteroarenes using photoredox catalysis is reported. Additionally, this method features the use of simple, commercially available carboxylic acid derivatives as alkylating agents, enabling the facile alkylation of a variety of biologically relevant heterocyclic scaffolds under mild conditions.