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Naphthyridine
Diazanaphthalenes are a class of aromatic heterocyclic chemical compounds that have the formula C8H6N2. They consist of a naphthalene double ring in which two of the carbon atoms have been replaced with nitrogen atoms. There are ten positional isomers, which differ by the locations of the nitrogen atoms. The group consist of two subgroups: *four ''benzodiazines'' with both N atoms in one ring: cinnoline, quinazoline, quinoxaline A quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. It is isomeric with other naphthyridines including quinazoline, phthalazine and ..., and phthalazine *six ''naphthyridines'' with one N atom in each ring Isomers References {{reflist ...
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1,8-Naphthyridine
1,8-Naphthyridine is an organic compound with the formula C8H6N2. It is the most well-studied of the six isomeric naphthyridines, a subset of diazanaphthalenes with nitrogen in the separate rings. Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones. Coordination chemistry With flanking nitrogen centers, 1,8-naphthyridine serves as a binucleating ligand in coordination chemistry A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many .... References {{DEFAULTSORT:Naphthyridine, 1,8- Naphthyridines ...
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1,8-naphthyridine
1,8-Naphthyridine is an organic compound with the formula C8H6N2. It is the most well-studied of the six isomeric naphthyridines, a subset of diazanaphthalenes with nitrogen in the separate rings. Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones. Coordination chemistry With flanking nitrogen centers, 1,8-naphthyridine serves as a binucleating ligand in coordination chemistry A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many .... References {{DEFAULTSORT:Naphthyridine, 1,8- Naphthyridines ...
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Quinoxaline
A quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. It is a colorless oil that melts just above room temperature. Although quinoxaline itself is mainly of academic interest, quinoxaline derivatives are used as dyes, pharmaceuticals (such as varenicline), and antibiotics such as olaquindox, carbadox, echinomycin, levomycin and actinoleutin. Synthesis They can be formed by condensing ''ortho''-diamines with 1,2-diketones. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones. Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2, ...
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Cinnoline
Cinnoline is an aromatic heterocyclic compound with the formula C8H6N2. It is isomeric with other naphthyridines including quinoxaline, phthalazine and quinazoline. Properties The free base can be obtained as an oil by treatment of the hydrochloride with base. It co-crystallizes with one molecule of ether as white silky needles, (m.p. 24–25 °C) upon cooling ethereal solutions. The free base melts at 39 °C. It has a taste resembling that of chloral hydrate and leaves a sharp irritation for some time. Cinnoline derivatives are obtained from oxycinnoline carboxylic acid, which is formed by digesting orthophenyl propiolic acid diazo chloride with water. Oxycinnoline carboxylic acid on heating gives oxycinnoline, melting at 225 °C, which with phosphorus pentachloride gives chlorcinnoline. This substance is reduced by iron filings and sulfuric acid to dihydrocinnoline. Discovery and synthesis The compound was first obtained in impure form by cyclization ...
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Phthalazine
Phthalazine, also called benzo-orthodiazine or benzopyridazine, is a heterocyclic organic compound with the molecular formula C8H6N2. It is isomeric with other naphthyridines including quinoxaline, cinnoline and quinazoline. Synthesis Phthalazine can be obtained by the condensation of w-tetrabromorthoxylene with hydrazine, or by the reduction of chlorphthalazine with phosphorus and hydroiodic acid. Properties It possesses basic properties and forms addition products with alkyl iodides. Reactions Upon oxidation with alkaline potassium permanganate it yields pyridazine dicarboxylic acid. Zinc and hydrochloric acid decompose it with formation of orthoxylylene diamine. The keto-hydro derivative phthalazone (C8H6ON2), is obtained by condensing hydrazine with orthophthalaldehydoacid. On treatment with phosphorus oxychloride, it yields a chlorphthalazine, which with zinc and hydrochloric acid gives isoindole (C8H7N), and with tin and hydrochloric acid, phthalimidine (C8H7ON), t ...
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Aromaticity
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term ''aromaticity'' with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning. Since the most common aromatic compounds are derivatives of benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word ''aromatic'' occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many non-be ...
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