19658-59-4

Usage

Explanation

The molecular formula represents the number of atoms of each element present in a molecule of the compound.
2. Carbonyl chloride derivative

Explanation

The compound contains a carbonyl chloride group (C=O) bonded to a carbon atom.
3. Dioxoloquinoline structure

Explanation

The compound has a fused ring system consisting of a dioxolane ring (a six-membered ring with two oxygen atoms) and a quinoline ring (a tricyclic system with a benzene and a pyridine ring fused together).
4. Ethyl substituent

Explanation

The compound has an ethyl group (-CH2CH3) attached to the dioxoloquinoline structure.
5. 5,8-dihydro

Explanation

The compound has two hydrogen atoms (dihydro) incorporated into the molecule, specifically at positions 5 and 8 of the dioxoloquinoline structure.
6. 8-oxo

Explanation

The compound has an oxygen atom (oxo) at position 8 of the dioxoloquinoline structure, indicating the presence of a carbonyl group (C=O) at that position.
7. Used in organic synthesis

Explanation

The compound serves as a building block or intermediate in the synthesis of various organic compounds.
8. Pharmaceutical research

Explanation

The compound is utilized in the development of biologically active compounds, which may have potential applications in the pharmaceutical industry.
9. Biologically active compounds

Explanation

The compound can be used to create molecules with biological activity, which may have therapeutic or medicinal properties.
10. Valuable and versatile intermediate

Explanation

Due to its unique structure and reactivity, the compound is considered a valuable and versatile intermediate in the development of new drugs and other organic compounds.

InChI:InChI=1/C13H10ClNO4/c1-2-15-5-8(13(14)17)12(16)7-3-10-11(4-9(7)15)19-6-18-10/h3-5H,2,6H2,1H3

Upstream product

• 32953-14-3 N-ethyl-3,4-(methylenedioxy)aniline 
• 16172-03-5 ethyl 5-ethyl-5,8-dihydro-8-oxo-1,3-dioxolo<4,5-g>quinoline-7-carboxylate 
• 32953-23-4 Ethyl α-ethoxycarbonyl-β-N-(5-benzodioxolyl)-N-ethylaminoacrylate 
• 14698-29-4 oxolinic Acid 

Downstream Products

• 110261-15-9 5-Ethyl-8-oxo-5,8-dihydro-1,3-dioxolo<4,5-g>quinoline-7-carboxylic ethoxycarbonylmethylamide 
• 57147-33-8 nitrile of 1-ethyl-6,7-methylenedioxy-4-oxo-1,4-dihydroquinoline-3-carbonic acid 
• 110261-16-0 2-[(5-Ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carbonyl)-amino]-butyric acid 
• 104571-64-4 3-N-(1-Ethyl-1,4-Dihydro-6,7-Methylenedioxy-4-Oxoquinoline-3-Carbonyl)Aminopropionic Acid 
• 97515-38-3 2-(5-ethyl-8-oxo-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxamido)acetate 
• 135922-55-3 5-Ethyl-8-oxo-5,8-dihydro-[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid 2-methoxy-phenyl ester 
• 136281-52-2 oxolinic acid tris(hydroxymethyl)methylamide 
• 110261-17-1 5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo<4,5-g>quinoline-3-carboxylic 1-adamantylamide 

Relevant academic research and scientific papers

Dual role of Rh(III) catalyst enables regioselective halogenation of (electron-rich) heterocycles

The Rh(III)-catalyzed selective bromination and iodination of electron-rich heterocycles is reported. Kinetic investigations show that Rh plays a dual role in the bromination, catalyzing the directed halogenation and preventing the inherent halogenation of these substrates. As a result, this method gives highly selective access to valuable halogenated heterocycles with regiochemistry complementary to those obtained using uncatalyzed approaches, which rely on the inherent reactivity of these classes of substrates. Furans, thiophenes, benzothiophenes, pyrazoles, quinolones, and chromones can be applied.

Synthesis of 5-ethyl-8-oxo-5.8-dihydro-1,3-dioxolo [4,5-g] quinolines and related compounds

Condensation of N-ethyl-3,4-methylenedioxyaniline 1 with diethyl ethoxymethylenemalonate 2 gave the unsaturated ester 3 which on thermal cyclization in refluxing diphenyl oxide gave ester 4. The ester on basic hydrolysis formed free acid 5 which upon treatment with thionyl chloride gave the acid chloride 6. Treatment of 6 with o-phenylenediamine, hydrazine hydrate, ammonia, urea and thiourea gave the amides (7-11). CS2 treatment in presence of KOH on 8 gave 12. 7-12 were prepared by conventional as well as under microwave irradiation. These compounds have been characterized on the basis of elemental analysis, IR, NMR and MS data.

Microwave-assisted synthesis of quinolone derivatives and related compounds

(Chemical Equation Presented) The Gould-Jacob type of reaction for the synthesis of ethyl 5-ethyl-8-oxo-5,8-dihydro-[1,3]-dioxolo[ 4,5-g]quinoline-7- carboxylate 4 has been carried out conventionally by the condensation between N-ethyl-3,4-methylenedioxyaniline 1 and diethyl ethoxymethylenemalonate 2 gave the unsaturated ester 3 and thermal cyclization in refluxing diphenyl oxide gave quinolone ethyl ester 4 and the results obtained were compared with single step microwave irradiation under solvent free conditions for the synthesis of 4. The esters on basic hydrolysis formed free acid 5, which, upon treatment with thionyl chloride gave the acid chloride 6. Treatment of acid chloride with o-phenylenediamine, hydrazine hydrate, ammonia, urea, and thiourea gave the amides (7-11). CS2 treatment in presence of KOH on 8 gave 12. We prepared 7-12 derivatives by conventional as well as microwave irradiation. These compounds have been characterized on the basis of IR, 1H NMR, MS, and elemental analysis. All the compounds prepared herein were screened for their antibacterial activity. Compounds 4, 5 possess promising antibacterial activity and compound 8 showed significant antibacterial activity.

Synthese et activite biologique de prodrogues de l'acide oxolinique

Synthesis and biological activities of oxolinic acid pro-drugs.Antiseptic phenols, anti-inflammatory acids and polyethyleneglycol moieties have been attached by labile bonds to oxolinic acid giving pro-drugs with anti-bacterial activities.Some of them are more soluble in water, exhibit a more sustained action in the time and give higher plasma and tissue concentrations compared with the free drug.