Imidazolone
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Imidazolone
Imidazolones are a family of heterocyclic compounds, the parents of which have the formula OC(NH)2(CH)2. Two isomers are possible, depending on the location of the carbonyl (CO) group. The NH groups are nonadjacent. A common route to imidazol-2-ones involves condensation of ureas and acyloins. Some are of interest in the pharmaceuticals.{{cite journal, journal=Chemistry of Heterocyclic Compounds, year=2015, volume=51, page=395–420 , title=Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones, first1=Maria M., last1=Antonova, first2=Vladimir V., last2=Baranov, first3=Angelina N., last3=Kravchenko, doi=10.1007/s10593-015-1716-3 4-Imidazolones arise from the condensation of amidines with 1,2-dicarbonyls such as glyoxal Glyoxal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of .. ...
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Glyoxal
Glyoxal is an organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ... with the chemical formula OCHCHO. It is the smallest dialdehyde (a compound with two aldehyde groups). It is a crystalline solid, white at low temperatures and yellow near the melting point (15 °C). The liquid is yellow, and the vapor is green.O'Neil, M.J. (2001): ''The Merck Index'', 13th Edition, page 803. Pure glyoxal is not commonly encountered because glyoxal is usually handled as a 40% aqueous solution (density near 1.24 g/mL). It forms a series of hydrates, including oligomers. For many purposes, these hydrated oligomers behave equivalently to glyoxal. Glyoxal is produced industrially as a precursor to many products. Production Glyoxal was first prepared and named by the German-British ...
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Heterocyclic Compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of heterocyclic chemistry focuses especially on unsaturated derivatives, and the preponderance of work and applications involves unstrained 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of heterocycles refers to those fused to benzene rings. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are quinol ...
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Isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is 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 "isomer" () is a back-for ...
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Acyloin
Acyloins or α-hydroxy ketones are a class of organic compounds which all possess a hydroxy group adjacent to a ketone group. The name acyloin is derived from the fact that they are formally derived from reductive coupling of carboxylic acyl groups. Synthesis Classic organic reactions exist for the synthesis of acyloins. * The acyloin condensation is a reductive coupling of esters * The benzoin condensation is condensation reaction between aldehydes catalyzed by a nucleophile * Oxidation of carbonyls is possible with molecular oxygen but not selective * Better alternative is oxidation of corresponding silyl enol ethers with ''m''CPBA in the Rubottom oxidation * MoOPH oxidation of carbonyls is a system with molybdenum peroxide, pyridine and hexamethylphosphoramide. Enolate oxidation by sulfonyloxaziridines Enolates can be oxidized by sulfonyloxaziridines. The enolate reacts by nucleophilic displacement at the electron deficient oxygen of the oxaziridine ring. : This rea ...
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Amidine
Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2. Examples of amidines include: * DBU * diminazene * benzamidine * Pentamidine * Paranyline Preparation A common route to primary amidines is the Pinner reaction. Reaction of the nitrile with alcohol in the presence of acid gives an iminoether. Treatment of the resulting compound with ammonia then completes the conversion to the amidine. Instead of using a Bronsted acid, Lewis acids such as aluminium trichloride promote the direct amination of nitriles. They are also generated by amination of an imidoyl chloride. They are also prepared by the addition of organolithium reagents to diimines, followed by protonation or alkylation. Dimethylformamide acetal reacts with primary amines to give amidines: :Me2NC(H)(OMe)2 + RNH2 → Me2NC=NHR + 2 MeOH Properties and appl ...
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