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Quinolines
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, str ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Combes Quinoline Synthesis
The Combes quinoline synthesis is a chemical reaction, which was first reported by Combes in 1888. Further studies and reviews of the Combes quinoline synthesis and its variations have been published by Alyamkina ''et al''., Bergstrom and Franklin, Born, and Johnson and Mathews. The Combes quinoline synthesis is often used to prepare the 2,4-substituted quinoline backbone and is unique in that it uses a β- diketone substrate, which is different from other quinoline preparation methods, such as the Conrad-Limpach synthesis and the Doebner reaction. It involves the condensation of unsubstituted anilines (1) with β-diketones (2) to form substituted quinolines (4) after an acid-catalyzed ring closure of an intermediate Schiff base (3). Mechanism The reaction mechanism undergoes three major steps, the first one being the protonation of the oxygen on the carbonyl in the β-diketone, which then undergoes a nucleophilic addition reaction with the aniline. An intramolecular pro ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Royal Society Of Chemistry
The Royal Society of Chemistry (RSC) is a learned society and professional association in the United Kingdom with the goal of "advancing the chemistry, chemical sciences". It was formed in 1980 from the amalgamation of the Chemical Society, the Royal Institute of Chemistry, the Faraday Society, and the Society for Analytical Chemistry with a new Royal Charter and the dual role of learned society and professional body. At its inception, the Society had a combined membership of 49,000 in the world. The headquarters of the Society are at Burlington House, Piccadilly, London. It also has offices in Thomas Graham House in Cambridge (named after Thomas Graham (chemist), Thomas Graham, the first president of the Chemical Society) where ''RSC Publishing'' is based. The Society has offices in the United States, on the campuses of The University of Pennsylvania and Drexel University, at the University City Science Center in Philadelphia, Pennsylvania, in both Beijing and Shanghai, People' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isomers
In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural (or constitutional) isomerism, in which '' bonds'' between the atoms differ; and stereoisomerism (or spatial isomerism), in which the bonds are the same but the ''relative positions'' of the atoms differ. Isomeric relationships form a hierarchy. Two chemicals might be the same constitutional isomer, but upon deeper analysis be stereoisomers of each other. Two molecules that are the same stereoisomer as each other might be in different conformational forms or be different isotopologues. The depth of analysis depends on the field of study or the chemical and physical properties of interest. The English word ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Doebner Reaction
The Doebner reaction is the chemical reaction of an aniline with an aldehyde and pyruvic acid to form quinoline-4-carboxylic acids. The reaction serves as an alternative to the Pfitzinger reaction. 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, 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 benzene ring and two proton shifts, the quinoline-4-carboxylic acid (4) is formed by water elimination: An alternative mechanism is based on the aniline and the aldehyde forming at first the Schiff base upon water elimination. The subsequent reaction with the enol form of pyruvic acid (1) leads to the formation of the above-mentioned aniline derivative (3) followed by the above-described ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
