32413-08-4

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl 2,3-quinolinedicarboxylate is used as a key intermediate in the synthesis of pharmaceuticals for its antitumor and antiviral properties. It contributes to the development of new drugs targeting a variety of diseases, including cancer and viral infections.
Used in Agrochemical Industry:
In the agrochemical sector, Diethyl 2,3-quinolinedicarboxylate is employed as a precursor in the production of agrochemicals, potentially enhancing crop protection and management strategies through its incorporation into effective and targeted compounds.
Used in Organic Synthesis:
Diethyl 2,3-quinolinedicarboxylate serves as a versatile building block in organic synthesis, particularly for the creation of heterocyclic compounds. Its utility in this field is instrumental in advancing pharmaceutical research and drug development, facilitating the discovery and synthesis of novel therapeutic agents.

InChI:InChI=1/C15H15NO4/c1-3-19-14(17)11-9-10-7-5-6-8-12(10)16-13(11)15(18)20-4-2/h5-9H,3-4H2,1-2H3

Upstream product

• 75-03-6 ethyl iodide 
• 64-17-5 ethanol 
• 529-23-7 o-aminobenzaldehyde 
• 108-56-5 diethyl oxaloacetate 
• 7732-18-5 water 
• 503-38-8 trichloromethyl chloroformate 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 13066-19-8 2-(2-phenylethenyl)benzenamine 
• 27652-35-3 (E)-2-styrylaniline 
• 552-89-6 2-nitro-benzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 7071-15-0 diethyl 2-(diethoxyphosphoryl)succinate 
• 271-61-4 benzo[c]isothiazole 
• 92525-68-3 Diethyl Quinoline-2,3-dicarboxylate N-Oxide 

Downstream Products

• 81335-37-7 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-Yl]-3-quinolinecarboxylic acid 
• 115787-29-6 potassium salt of 2-(5-isopropyl-5-methyl-4-oxoimidazolin-2-yl)-3-quinolinecarboxylic acid 
• 643-38-9 quinoline-2,3-dicarboxylic acid 
• 129281-03-4 quinoline-2,3-dicarboxylic acid diamide 

Relevant academic research and scientific papers

Selective reductive annulation reaction for direct synthesis of functionalized quinolines by a cobalt nanocatalyst

Due to the extensive applications of quinolines, the search for selective construction of such products has long been an attractive subject in scientific community. Herein, by developing a new N-doped ZrO2@C supported cobalt nanomaterial, it has been successfully applied as an efficient catalyst for the reductive annulation of 2-nitroaryl carbonyls with alkynoates and alkynones. The catalytic transformation allows synthesizing a wide array of funcitonalized quinolines with the merits of broad substrate scope, good functional group tolerance, excellent hydrogen transfer selectivity, reusable earth-abundant metal catalyst, and operational simplicity. The developed chemistry paves the ways for further design of hydrogen transfer-mediated coupling reactions by developing heterogeneous catalysts with suitable supports.

Metal-Free Oxidative Annulation/Cyclization of 1,6-Enynes for the Synthesis of 4-Carbonylquinolines

Herein we report on the development of a metal-free oxidative annulation reaction of 1,6-enynes, leading to 4-carbonylquinolines by using dioxygen as a green sustainable oxidant. Key advances include the use of readily available tert-butyl nitrite (TBN) to promote radical annulation of 1,6-enynes and easy-to-handle reaction conditions. Preliminary mechanistic studies including radical capture reactions and isotope labelling experiments are also conducted. (Figure presented.).

Visible-Light Induced and Oxygen-Promoted Oxidative Cyclization of Aromatic Enamines for the Synthesis of Quinolines Derivatives

The dual transition metal-visible light photoredox catalysis for the synthesis of quinoline derivatives by using dioxygen as an oxygen source is developed. By using visible light, the direct oxidative cyclization of aromatic enamines with alkynes or alkenes can be achieved at mild conditions with an aid of copper or palladium catalysts, and a variety of multisubstituted quinoline derivatives could be obtained in good to moderate yields under mild reaction conditions.

InCl3-driven regioselective synthesis of functionalized/ annulated quinolines: Scope and limitations

The efficient, regioselective synthesis of functionalized/annulated quinolines was achieved by the coupling of 2-aminoaryl ketones with alkynes/active methylenes/α-oxoketene dithioacetals promoted by InCl 3 in refluxing acetonitrile as well as under solvent-free conditions in excellent yields. This transformation presumably proceeded through the hydroamination-hydroarylation of alkynes, and the Friedlaender annulation of active methylene compounds and α-oxoketene dithioacetals with 2-aminoarylketones. In addition, simple reductive and oxidative cyclization of 2-nitrobenzaldehyde and 2-aminobenzylalcohol, respectively, afforded substituted quinolines. Systematic optimization of the reaction parameters allowed us to identify two-component coupling (2CC) conditions that were tolerant of a wide range of functional groups, thereby providing densely functionalized/annulated quinolines. This approach tolerates the synthesis of various bioactive quinoline frameworks from the same 2-aminoarylketones under mild conditions, thus making this strategy highly useful in diversity-oriented synthesis (DOS). The scope and limitations of the alkyne-, activated methylene-, and α-oxoketene dithioacetal components on the reaction were also investigated.

Process for preparing pyridine and quinoline derivatives

The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives which can be dehydrated to 2-aminobut-2-ene dioic acid derivatives, which can be subsequently converted to pyridine and quinoline derivatives.

Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof

There is provided a novel process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof.

REACTIONS OF 2,1-BENZISOTHIAZOLES WITH ACETYLENIC ESTERS

2,1-Benzisothiazole and the 3-methyl derivative react with dimethyl acetylenedicarboxylate (DMAD) under forcing conditions by addition across the heterodiene and loss of sulphur to afford dimethyl quinoline-2,3-dicarboxylate and the corresponding 4-methyl derivative, respectively.Diethyl acetylenedicarboxylate and methyl propiolate react similarly but in very low yield.These reactions could involve initial Michael-type attack of the acetylenic ester on the heterocyclic nitrogen or concerted cycloaddition. 3-Amino-2,1-benzisothiazole and DMAD react differently to yield dimethyl 2-cyanoanilinofumarate; a possible mechanism is presented.