Diazanaphthalenes

In chemistry, the diazanaphthalenes form a group of organic compounds that belong to the heterocycles (more precisely: heteroaromatics ). They consist of a naphthalene ring in which two carbon atoms have been replaced by nitrogen. Their different arrangement results in ten isomers with the empirical formula C ₈ H ₆ N ₂ .

The entire group is divided into two subgroups:

• four benzodiazines with both N atoms in only one ring: quinazoline , quinoxaline , cinnoline and phthalazine
• six naphthyridines or pyridopyridines with one nitrogen atom per ring

Isomers

Surname	Structural formula	Subgroup
1,2-diazanaphthalene ( cinnoline )		Benzodiazine
1,3-diazanaphthalene ( quinazoline )		Benzodiazine
1,4-diazanaphthalene ( quinoxaline )		Benzodiazine
1,5-diazanaphthalene		Naphthyridine
1,6-diazanaphthalene		Naphthyridine
1,7-diazanaphthalene		Naphthyridine
1,8-diazanaphthalene		Naphthyridine
2,3-diazanaphthalene ( phthalazine )		Benzodiazine
2,6-diazanaphthalene		Naphthyridine
2,7-diazanaphthalene		Naphthyridine

Individual evidence

1. ↑ Entry on naphthyridines. In: Römpp Online . Georg Thieme Verlag, accessed on August 28, 2014.
2. ↑ Desmond J. Brown, Jonathan A. Ellman, Edward C. Taylor: The Chemistry of Heterocyclic Compounds, The Naphthyridines , John Wiley & Sons, 2007 ( limited preview in Google Book Search).
3. ^ William W. Paudler, Thomas J. Kress: Naphthyridine chemistry. IX. Bromination and animation of the 1, X-naphthyridines , J. Org. Chem. , 1968 , 33  (4), pp. 1384-1387 ( doi : 10.1021 / jo01268a018 ).