Diazanaphthalene

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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:

Isomers

NamesStructureSubgroup CAS RN
1,2-diazanaphthalene
(cinnoline)
1,2-naphthyridine cinnoline.svg benzodiazine253-66-7
2,3-diazanaphthalene
(phthalazine)
2,3-naphthyridine phthalazine.svg benzodiazine253-52-1
1,3-diazanaphthalene
(quinazoline)
1,3-naphthyridine quinazoline.svg benzodiazine253-82-7
1,4-diazanaphthalene
(quinoxaline)
1,4-naphthyridine quinoxaline.svg benzodiazine91-19-0
1,7-naphthyridine
(1,7-diazanaphthalene)
1,7-naphthyridine.svg naphthyridine253-69-0
1,8-Naphthyridine
(1,8-diazanaphthalene)
1,8-naphthyridine.svg naphthyridine254-60-4
2,7-naphthyridine
(2,7-diazanaphthalene)
2,7-naphthyridine.svg naphthyridine253-45-2
1,6-naphthyridine
(1,6-diazanaphthalene)
1,6-naphthyridine.svg naphthyridine253-72-5
1,5-naphthyridine
(1,5-diazanaphthalene)
1,5-naphthyridine.svg naphthyridine254-79-5
2,6-naphthyridine
(2,6-diazanaphthalene)
2,6-naphthyridine.svg naphthyridine253-50-9

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<span class="mw-page-title-main">Heterocyclic compound</span> Molecule with one or more rings composed of different elements

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<span class="mw-page-title-main">1,8-Naphthyridine</span> Chemical compound

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.

References

  1. Desmond J. Brown, Jonathan A. Ellman, Edward C. Taylor: The Chemistry of Heterocyclic Compounds, The Naphthyridines, John Wiley & Sons, 2007.
  2. Paudler, William W.; Kress, Thomas J. (1968). "Naphthyridine chemistry. IX. Bromination and animation of the 1,X-naphthyridines". The Journal of Organic Chemistry. 33 (4): 1384–1387. doi:10.1021/jo01268a018.