Camps Quinoline Synthesis
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Camps Quinoline Synthesis
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. A ...
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Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ...
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Hydroxide
Hydroxide is a diatomic anion with chemical formula OH−. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate in aqueous solution, liberating solvated hydroxide ions. Sodium hydroxide is a multi-million-ton per annum commodity chemical. The corresponding electrically neutral compound HO• is the hydroxyl radical. The corresponding covalently bound group –OH of atoms is the hydroxy group. Both the hydroxide ion and hydroxy group are nucleophiles and can act as catalysts in organic chemistry. Many inorganic substances which bear the word ''hydroxide'' in their names are not ionic compounds of the hydroxide ion, but covalent compounds which contain hydroxy groups. Hydroxide ion The hydroxide ion is a natural par ...
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Chemische Berichte
''Chemische Berichte'' (usually abbreviated as ''Ber.'' or ''Chem. Ber.'') was a German-language scientific journal of all disciplines of chemistry founded in 1868. It was one of the oldest scientific journals in chemistry, until it merged with ''Recueil des Travaux Chimiques des Pays-Bas'' to form ''Chemische Berichte/Recueil'' in 1997. ''Chemische Berichte/Recueil'' was then merged with other European journals in 1998 to form ''European Journal of Inorganic Chemistry''. History Founded in 1868 as ''Berichte der Deutschen Chemischen Gesellschaft'' (, CODEN BDCGAS), it operated under this title until 1928 (Vol. 61). The journal was then split into: * ''Berichte der Deutschen Chemischen Gesellschaft, A: Vereins-Nachrichten'' (, CODEN BDCAAS), and * ''Berichte der Deutschen Chemischen Gesellschaft, B: Abhandlungen'' (, CODEN BDCBAD). Vol. 78 and 79 (1945–1946) were omitted and not published due to World War II. The journal was renamed ''Chemische Berichte'' (, CODEN CHBEAM) in 19 ...
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Arch
An arch is a vertical curved structure that spans an elevated space and may or may not support the weight above it, or in case of a horizontal arch like an arch dam, the hydrostatic pressure against it. Arches may be synonymous with vaults, but a vault may be distinguished as a continuous arch forming a roof. Arches appeared as early as the 2nd millennium BC in Mesopotamian brick architecture, and their systematic use started with the ancient Romans, who were the first to apply the technique to a wide range of structures. Basic concepts An arch is a pure compression form. It can span a large area by resolving forces into compressive stresses, and thereby eliminating tensile stresses. This is sometimes denominated "arch action". As the forces in the arch are transferred to its base, the arch pushes outward at its base, denominated "thrust". As the rise, i. e. height, of the arch decreases the outward thrust increases. In order to preserve arch action and prevent collapse ...
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Chem
Chem may refer to: * Chemistry practical waali mam *Chemistry *Chemical * ''Chem'' (journal), a scientific journal published by Cell Press *Post apocalyptic slang for "drugs", medicinal or otherwise in the Fallout video game series. In Ancient Egyptian usage: * ''Khem'' (also spelt ''Chem''), the Egyptian word for "black" * Min (god), in the past erroneously named ''Khem'' CHEM may refer to : *A metabolic panel: for instance, CHEM-7, which is the basic metabolic panel *CHEM-DT CHEM-DT is the TVA owned-and-operated television station in Trois-Rivières, Quebec, Canada. It broadcasts a high-definition digital signal on VHF channel 8 from a transmitter on Rue Principale in Notre-Dame-du-Mont-Carmel. Owned by the Grou ..., a Canadian television channel See also * Chemo (other) * Kemi, a place in Finland {{disambig ...
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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 *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) *Kempes Kempes is a surname. Notable people with the surname include: * Mario Kem ...
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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, stry ...
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Keto-enol Tautomerism
In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The terms ''enol'' and ''alkenol'' are portmanteaus deriving from "-ene"/"alkene" and the "-ol" suffix indicating the hydroxyl group of alcohols, dropping the terminal "-e" of the first term. Generation of enols often involves removal of a hydrogen adjacent (α-) to the carbonyl group—i.e., deprotonation, its removal as a proton, . When this proton is not returned at the end of the stepwise process, the result is an anion termed an enolate (see images at right). The enolate structures shown are schematic; a more modern representation considers the molecular orbitals that are formed and occupied by electrons in the enolate. Similarly, generation of the enol often is accompanied by "trapping" or masking of the hydroxy group as an ether, such as ...
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Quinolone
Quinolone may refer to: * 2-Quinolone * 4-Quinolone * Quinolone antibiotic A quinolone antibiotic is a member of 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 we ...s {{Short pages monitor ...
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Doebner Reaction
The Doebner reaction is the chemical reaction of an aniline with an aldehyde and pyruvic acid to form quinoline-4-carboxylic acids.Bergstrom, F. W. ''Chem. Rev.'' 1944, ''35'', 156. (Review) The reaction serves as an alternative to the Pfitzinger reaction.W. Pfitzinger: ''Chinolinderivate aus Isatinsäure.'' In: ''Journal für Praktische Chemie.'' Band 33, Nr. 1, 1886, S. 100, doi:10.1002/prac.18850330110.Oscar Doebner: ''Ueber α-Alkylcinchoninsäuren und α-Alkylchinoline.'' In: ''Justus Liebigs Annalen der Chemie.'' Band 242, Nr. 3, 1887, S. 265–388, doi:10.1002/jlac.18872420302. Reaction mechanism The reaction mechanism is not exactly known, two proposals are presented here. One possibility is at first an aldol condensation, starting from the enol form of the pyruvic acid (1) and the aldehyde, forming an ''β,γ''-unsaturated α-ketocarboxylic acid (2). This is followed by a Michael addition with aniline to form an aniline derivative (3). After a cyclization at the benze ...
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