Anthranil (2,1-benzisoxazole) is an organic compound with a molecular formula C₇H₅NO, which features a fused

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms ...

isoxazole Isoxazole is an electron-rich azole with an oxygen atom next to the nitrogen. It is also the class of compounds containing this ring. Isoxazolyl is the univalent radical derived from isoxazole. Occurrence Isoxazole rings are found in some natura ...

bicyclic ring structure. It is an isomer of the more common compounds

benzoxazole Benzoxazole is an aromatic organic compound with a molecular formula C7H5NO, a benzene-fused oxazole ring structure, and an odor similar to pyridine. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are co ...

and

benzisoxazole 1,2-Benzisoxazole is an aromatic organic compound with a molecular formula C7H5NO containing a benzene-fused isoxazole ring structure. The compound itself has no common applications; however, functionalized benzisoxazoles and benzisoxazoyls have ...

, which have their oxygen atoms located in the 1-position. The locations of the heteroatoms in anthranil results in disrupted

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 satur ...

, making it by far the least stable of the 3 structural isomers.

References

Aromatic bases Simple aromatic rings {{heterocyclic-stub