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

A. A. Abramov; M. V. Kulagina; N. A. Gavrilova; E. S. Semichenko; A. A. Kondrasenko; G. A. Suboch

doi:10.1134/S1070428019080256

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

Authors: Abramov A.A.¹, Kulagina M.V.¹, Gavrilova N.A.¹, Semichenko E.S.¹, Kondrasenko A.A.²^,3, Suboch G.A.¹
Affiliations:
1. Reshetnev Siberian State University of Science and Technology
2. Institute of Chemistry and Chemical Technology, Krasnoyarsk Research Center, Siberian Branch
3. Kirenskii Institute of Physics, Krasnoyarsk Research Center, Siberian Branch
Issue: Vol 55, No 8 (2019)
Pages: 1234-1237
Section: Short Communications
URL: https://journal-vniispk.ru/1070-4280/article/view/221124
DOI: https://doi.org/10.1134/S1070428019080256
ID: 221124

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Abstract

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.