Aromatic substitution by n-arylhydroxylamines—I

Add time:07/13/2019    Source:sciencedirect.com

Thermolysis of 8-hydroxylamino-6-methoxyquinoline at 65° in methanol gave 8-amino-5,8′-iminobis(6-methoxyquinoline), the same product being formed by thermolysis of 8-azido-6-methoxyquinoline as well as by deoxygenation of 6-methoxy-8-nitroquinoline with triethylphosphite in the presence of 8-amino-6-methoxyquinoline. Solvent effects were also consistent with the involvement of a nitrenoid species in these intermolecular aromatic substitutons. 8-Hydroxylaminoquinoline behaved in an analogous fashion but no iminobis compound was obtained from the corresponding 6-hydroxylaminoquinoline, indicating an internal interaction of the ring N atom with the 8-hydroxylamino function. Thermolysis of 8-hydroxylamino-6-methoxyquinoline in the presence of amines gave rise to o-diamines reconcilable with a nitrene intermediate.

We also recommend Trading Suppliers and Manufacturers of 6-METHOXYQUINOLINE N-OXIDE (cas 6563-13-9). Pls Click Website Link as below: cas 6563-13-9 suppliers

Prev:A highly practical and convenient halogenation of fused heterocyclic N-oxides
Next:Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids)