4-Quinolones
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4-Quinolones
4-Quinolone is an organic compound derived from quinoline. It and 2-quinolone are the two most important parent (meaning simplified) quinolones. 4-Quinolone exists in equilibrium with a minor tautomer, 4-hydroxyquinoline (CAS#611-36-9). Aside from pedagogical interest, 4-quinolone is of little intrinsic value but its derivatives, the 4-quinolone antibiotics, represent a large class of important drugs. Synthesis The chemical synthesis of quinolones often involves ring-closing reactions.{{cite journal, title=Co(III)-Catalyzed Enaminone-Directed C-H Amidation for Quinolone Synthesis, author=Shi, Pengfei, author2=Wang, Lili, author3=Chen, Kehao, author4=Wang, Jie, author5=Zhu, Jin, journal= Organic Letters, year=2017, volume=19, issue=9, pages=2418–2421, pmid=28425721, doi=10.1021/acs.orglett.7b00968 Such reactions often install a hydroxyl group (an –OH functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecul ...
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Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ...
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Quinoline
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance. Occurrence and isolation Quinoline was first extracted from coal tar in 1834 by German chemist Friedlieb Ferdinand Runge; he called quinoline ''leukol'' ("white oil" in Greek). Coal tar remains the principal source of commercial quinoline. In 1842, French chemist Charles Gerhardt obtained a compound by dry distilling quinine, st ...
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2-quinolone
2-Quinolone is an organic compound related structurally to quinoline. It is the majority tautomer in equilibrium with 2-quinolinol. The compound can be classified as a cyclic amide, and as such is used as an isostere for peptides and other pharmaceutically inspired targets. The 4-methyl-2-quinolone can be prepared by dehydration of acetoacetanilide. The isomer 4-quinolone is the parent of a large class of antibiotics called quinolone antibiotics. A prominent example is ciprofloxacin, a broad spectrum antibiotic commonly used for treatment of various infections such as urinary tract infections (UTIs), typhoid, meningitis, gonorrhoea, syphilis Syphilis () is a sexually transmitted infection caused by the bacterium ''Treponema pallidum'' subspecies ''pallidum''. The signs and symptoms depend on the stage it presents: primary, secondary, latent syphilis, latent or tertiary. The prim ..., and skin infections. References External links * {{DEFAULTSORT:2-Quinolone
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Quinolone Antibiotic
Quinolone antibiotics constitute a large group of broad-spectrum bacteriocidals that share a bicyclic core structure related to the substance 4-quinolone. They are used in human and veterinary medicine to treat bacterial infections, as well as in animal husbandry, specifically poultry production. Quinolone antibiotics are classified into four generations based on their spectrum of activity and chemical modifications. The first-generation quinolones, such as nalidixic acid, primarily target Gram-negative bacteria and are mainly used for urinary tract infections. Second-generation quinolones introduced fluorine atoms into their structure, creating fluoroquinolones, which significantly expanded their antibacterial activity to include some Gram-positive bacteria. Third-generation fluoroquinolones further improved Gram-positive coverage, while fourth-generation fluoroquinolones offer broad-spectrum activity, including anaerobic bacteria. Only quinolone antibiotics in generat ...
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Chemical Synthesis
Chemical synthesis (chemical combination) is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In modern laboratory uses, the process is reproducible and reliable. A chemical synthesis involves one or more compounds (known as '' reagents'' or ''reactants'') that will experience a transformation under certain conditions. Various reaction types can be applied to formulate a desired product. This requires mixing the compounds in a reaction vessel, such as a chemical reactor or a simple round-bottom flask. Many reactions require some form of processing (" work-up") or purification procedure to isolate the final product. The amount produced by chemical synthesis is known as the '' reaction yield''. Typically, yields are expressed as a mass in grams (in a laboratory setting) or as a percentage of the total theoretical quantity that could be produced based ...
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Functional Group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The Reactivity (chemistry), reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive Chemical property, chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their Chemical polarity, nonp ...
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Camps Cyclization
The Camps quinoline synthesis (also known as the Camps cyclization) is a chemical reaction whereby an o-acylaminoacetophenone is transformed into two different hydroxyquinolines (products A and B) using hydroxide ion. The relative proportions of the hydroxyquinolines (A and B) produced are dependent upon the reaction conditions and structure of the starting material. Although the reaction product is commonly depicted as a quinoline (the enol form), it is believed that the keto form predominates in both the solid state and in solution, making the compound a quinolone. An example of the Camps reaction is given below:''Sequential Cu-Catalyzed Amidation-Base-Mediated Camps Cyclization: A Two-Step Synthesis of 2-Aryl-4-quinolones from o-Halophenones'' Jones, C. P.; Anderson, K. W.; Buchwald, S. L. J. Org. Chem.; (Article); 2007; 72(21); 7968-7973. The amides of 1,3-enaminoketones react to form pyridinones-2 under similar conditions. Camps Reaction and Related Cyclizations. ...
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Camps Quinoline Synthesis Scheme
Camps may refer to: People *Ramón Camps (1927–1994), Argentine general *Gabriel Camps (1927–2002), French historian *Luís Espinal Camps (1932–1980), Spanish missionary to Bolivia *Victoria Camps (b. 1941), Spanish philosopher and professor *Josep Piqué i Camps (b. 1955), Spanish politician * Octavia Camps, Uruguayan-American computer scientist * Francisco Camps (b. 1962), Spanish politician * Gerardo Camps, (b. 1963), Spanish politician * Patricio Camps (b. 1972), Argentine footballer Places In Argentina: *Estación Camps, village in Entre Ríos Province In France: *Camps-sur-l'Agly, commune in the Aude department *Camps-en-Amiénois, commune in the Somme department *Camps-la-Source, commune in the Var department *Camps-sur-l'Isle, commune in the Gironde department *Camps-Saint-Mathurin-Léobazel, commune in the Corrèze department See also *CAMPS, missile defense system for civilian aircraft *Camp (other) *Campus *Kamps (other) Kamps, a Dutch and German ...
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