Novel Derivatives of Adamantyl-substituted Quinolin-6-amines and Synthesis of Imidazo[4,5-f]quinolines Therefrom

Abramov, A. A.; Kulagina, M., V; Gavrilova, N. A.; Semichenko, E. S.; Kondrasenko, A. A.; Suboch, G. A. Source: RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 55 (8):1234-1237; 10.1134/S1070428019080256 AUG 2019

N-(Adamantan-1-yl)alkyl-substituted 5-nitrosoquinolin-6-amines were synthesized for the first time by the amination of 5-nitrosoquinolin-6-ol with primary N-[(adamantan-1-yl)alkyl]amines. The resulting nitrosoquinolinamines were reduced with hydrazine hydrate over Pd/C to N6-[(adamantan-1-yl)alkyl]quinoline-5,6-diamines. The latter were heated in formic acid to obtain previously unknown 3-[(adamantan-1-yl)alkyl]-3H-imidazo[4,5-f]quinolines.