1,8-Naphthyridine

Last updated
1,8-Naphthyridine
1,8-naphthyridine.svg
Names
Preferred IUPAC name
1,8-Naphthyridine [1]
Identifiers
3D model (JSmol)
109347
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.201.052 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 675-799-8
27124
PubChem CID
UNII
  • InChI=1S/C8H6N2/c1-3-7-4-2-6-10-8(7)9-5-1/h1-6H
    Key: FLBAYUMRQUHISI-UHFFFAOYSA-N
  • C1=CC2=C(N=C1)N=CC=C2
Properties
C8H6N2
Molar mass 130.150 g·mol−1
Appearanceyellow solid
Density 1.359 g/cm3
Melting point 98–99 °C (208–210 °F; 371–372 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [2] [3] Enoxacin, nalidixic acid, and trovafloxacin are 1,8-naphthyridine derivatives with antibacterial properties related to the fluoroquinolones. [4]

Coordination chemistry

With flanking nitrogen centers, 1,8-naphthyridine serves as a binucleating ligand in coordination chemistry. [5] [6]

Related Research Articles

<span class="mw-page-title-main">Amide</span> Organic compounds of the form RC(=O)NR′R″

In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula R−C(=O)−NR′R″, where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid with the hydroxyl group replaced by an amine group ; or, equivalently, an acyl (alkanoyl) group joined to an amine group.

<span class="mw-page-title-main">Beta-lactam</span> Family of chemical compounds

A beta-lactam (β-lactam) ring is a four-membered lactam. A lactam is a cyclic amide, and beta-lactams are named so because the nitrogen atom is attached to the β-carbon atom relative to the carbonyl. The simplest β-lactam possible is 2-azetidinone. β-lactams are significant structural units of medicines as manifested in many β-lactam antibiotics Up to 1970, most β-lactam research was concerned with the penicillin and cephalosporin groups, but since then, a wide variety of structures have been described.

<span class="mw-page-title-main">Pyridine</span> Heterocyclic aromatic organic compound

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide.

In chemistry, the oxidation state, or oxidation number, is the hypothetical charge of an atom if all of its bonds to other atoms were fully ionic. It describes the degree of oxidation of an atom in a chemical compound. Conceptually, the oxidation state may be positive, negative or zero. While fully ionic bonds are not found in nature, many bonds exhibit strong ionicity, making oxidation state a useful predictor of charge.

<span class="mw-page-title-main">Catenation</span> Bonding of atoms of the same element into chains or rings

In chemistry, catenation is the bonding of atoms of the same element into a series, called a chain. A chain or a ring shape may be open if its ends are not bonded to each other, or closed if they are bonded in a ring. The words to catenate and catenation reflect the Latin root catena, "chain".

<span class="mw-page-title-main">Phthalocyanine</span> Chemical compound

Phthalocyanine is a large, aromatic, macrocyclic, organic compound with the formula (C8H4N2)4H2 and is of theoretical or specialized interest in chemical dyes and photoelectricity.

<span class="mw-page-title-main">1,10-Phenanthroline</span> Heterocyclic organic compound

1,10-Phenanthroline (phen) is a heterocyclic organic compound. It is a white solid that is soluble in organic solvents. The 1,10 refer to the location of the nitrogen atoms that replace CH's in the hydrocarbon called phenanthrene.

An isocyanide is an organic compound with the functional group –N+≡C. It is the isomer of the related nitrile (–C≡N), hence the prefix is isocyano. The organic fragment is connected to the isocyanide group through the nitrogen atom, not via the carbon. They are used as building blocks for the synthesis of other compounds.

Pyrazole is an organic compound of azole group with the formula C3H3N2H. It is a heterocycle characterized by a 5-membered ring of three carbon atoms and two adjacent nitrogen atoms, which are in ortho-substitution. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugate acid 2.49 at 25 °C). Pyrazoles are also a class of compounds that have the ring C3N2 with adjacent nitrogen atoms. Notable drugs containing a pyrazole ring are celecoxib (celebrex) and the anabolic steroid stanozolol.

<span class="mw-page-title-main">Cinnoline</span> Chemical compound

Cinnoline is an aromatic heterocyclic compound with the formula C8H6N2. It is isomeric with other naphthyridines including quinoxaline, phthalazine and quinazoline.

<span class="mw-page-title-main">Phthalazine</span> Chemical compound

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.

<span class="mw-page-title-main">Fullerene chemistry</span>

Fullerene chemistry is a field of organic chemistry devoted to the chemical properties of fullerenes. Research in this field is driven by the need to functionalize fullerenes and tune their properties. For example, fullerene is notoriously insoluble and adding a suitable group can enhance solubility. By adding a polymerizable group, a fullerene polymer can be obtained. Functionalized fullerenes are divided into two classes: exohedral fullerenes with substituents outside the cage and endohedral fullerenes with trapped molecules inside the cage.

<span class="mw-page-title-main">Metal–organic framework</span> Class of chemical substance

Metal–organic frameworks (MOFs) are a class of compounds consisting of metal clusters coordinated to organic ligands to form one-, two-, or three-dimensional structures. The organic ligands included are sometimes referred to as "struts" or "linkers", one example being 1,4-benzenedicarboxylic acid (BDC).

In organometallic chemistry, extended metal atom chains (EMACs) are molecules that consist of a linear chain of directly bonded metal atoms, surrounded by organic ligands. These compounds represent the smallest molecular wires. Such species are researched for the bottom-up approach to nanoelectronics, although no applications are near term.

<i>N</i>-Sulfinyl imine

N-Sulfinyl imines are a class of imines bearing a sulfinyl group attached to nitrogen. These imines display useful stereoselectivity reactivity and due to the presence of the chiral electron withdrawing N-sulfinyl group. They allow 1,2-addition of organometallic reagents to imines. The N-sulfinyl group exerts powerful and predictable stereodirecting effects resulting in high levels of asymmetric induction. Racemization of the newly created carbon-nitrogen stereo center is prevented because anions are stabilized at nitrogen. The sulfinyl chiral auxiliary is readily removed by simple acid hydrolysis. The addition of organometallic reagents to N-sulfinyl imines is the most reliable and versatile method for the asymmetric synthesis of amine derivatives. These building blocks have been employed in the asymmetric synthesis of numerous biologically active compounds.

<span class="mw-page-title-main">Carbon quantum dot</span>

Carbon quantum dots also commonly called carbon dots are carbon nanoparticles which are less than 10 nm in size and have some form of surface passivation.

In chemistry, pyramidal inversion (also umbrella inversion) is a fluxional process in compounds with a pyramidal molecule, such as ammonia (NH3) "turns inside out". It is a rapid oscillation of the atom and substituents, the molecule or ion passing through a planar transition state. For a compound that would otherwise be chiral due to a stereocenter, pyramidal inversion allows its enantiomers to racemize. The general phenomenon of pyramidal inversion applies to many types of molecules, including carbanions, amines, phosphines, arsines, stibines, and sulfoxides.

The sulfate fluorides are double salts that contain both sulfate and fluoride anions. They are in the class of mixed anion compounds. Some of these minerals are deposited in fumaroles.

Sulfidogermanates or thiogermanates are chemical compounds containing anions with sulfur atoms bound to germanium. They are in the class of chalcogenidotetrelates. Related compounds include thiosilicates, thiostannates, selenidogermanates, telluridogermanates and selenidostannates.

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 212. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. Litvinov, Victor P.; Roman, Sergey V.; Dyachenko, Vladimir D. (2000). "Naphthyridines. Structure, Physicochemical Properties and General Methods of Synthesis". Russian Chemical Reviews. 69 (3): 201–220. Bibcode:2000RuCRv..69..201L. doi:10.1070/RC2000v069n03ABEH000553. S2CID   250827396.
  3. Dapporto, P.; Ghilardi, C. A.; Mealli, C.; Orlandini, A.; Pacinotti, S. (1984). "Low-Temperature (163 K) Structure of 1,8-Naphthyridine, C8H6N2". Acta Crystallographica Section C Crystal Structure Communications. 40 (5): 891–894. doi:10.1107/S0108270184006144.
  4. V. P. Litvinov (2006). Advances in the Chemistry of Naphthyridines. Advances in Heterocyclic Chemistry. Vol. 91. pp. 189–300. doi:10.1016/S0065-2725(06)91004-6. ISBN   9780120207916.
  5. Hua, Shao-An; Liu, Isiah Po-Chun; Hasanov, Hasan; Huang, Gin-Chen; Ismayilov, Rayyat Huseyn; Chiu, Chien-Lan; Yeh, Chen-Yu; Lee, Gene-Hsiang; Peng, Shie-Ming (2010). "Probing the electronic communication of linear heptanickel and nonanickel string complexes by utilizing two redox-active [Ni2(napy)4]3+ moieties". Dalton Transactions. 39 (16): 3890–6. doi:10.1039/b923125k. PMID   20372713.
  6. Bera, Jitendra K.; Sadhukhan, Nabanita; Majumdar, Moumita (2009). "1,8-Naphthyridine Revisited: Applications in Dimetal Chemistry". European Journal of Inorganic Chemistry. 2009 (27): 4023–4038. doi:10.1002/ejic.200900312.