R. Amaresh, P. Perumal
Nov 19, 1998
Citations
0
Influential Citations
23
Citations
Journal
Tetrahedron
Abstract
Abstract Studies have been carried out on a new novel method for the synthesis of 2-( N , N -disubstituted)aminoquinoline via intramolecular electrophilic substitution of methyleniminium salts by azide. Treatment of 1-(2-azidophenyl)ethanone with Vilsmeier reagent (DMF/POCl 3 ) gave 4-chloro-2-dimethylamino-3-quinolinecarboxaldehyde and 4-chloro-2-dimethylaminoquinoline, whereas 1-(2-azidophenyl)propanone and 1-(2-azidophenyl)butanone give unformylated products 4-chloro-3-methyl-2-dimethylaminoquinoline, 4-chloro-3-methylquinoline and 4-chloro-3-ethyl-2-dimethylaminoquinoline, 4-chloro-3-ethylquinoline respectively. The possible mechanisms for the formation of the products are discussed. The effect of the N , N -dimethylamino leaving group has been studied using sterically hindered N -methylformanilide(MFA), N -formylpiperidine(NFP) and N -formylmorpholine(NFM) instead of DMF.