SYNTHESIS OF NOVEL HYBRIDE MOLECULES CONTAINING INDOLE AND QUINOLINE CYCLES U.A. Kurbanov 1 , Sh.N. Zhurakulov 1,2 , V.I. Vinogradova 1 , T.S. Kholikov 2 1) S.Yu. Yunusov Institute of the Chemistry of Plant Substances Academy of sciences of the Republic of Uzbekistan st. Mirzo-Ulugbek, 77, 100170 Tashkent 2) National University of Uzbekistan named after Mirzo Ulugbek Quinoline alkaloids are of particular importance because they are important
biologically active compounds. Currently, many quinoline alkaloids are used in
medicine as drugs. For example: drotaverine is a phosphodiesterase-4 inhibitor used to
relieve spasms of the smooth muscles of the gastrointestinal tract. Levorphanol is used
in the treatment of moderate to severe pain. In order to obtain various biologically
active substances based on quinoline alkaloids, the reaction of 2-chloro-3-formyl-8-
methyl quinoline (
1 ) with tryptamine (
2 ) was carried out. The reaction of 2-chloro-3-
formyl-8-methyl quinoline with tryptamine had been carried out in benzene for 3 hours.
As a result of the reaction, imine N-(2-(1H-indol-3-yl)ethyl)-1-(2-chloro-8-
methylquinolin-3-yl)methanimine (
3 ) was formed. In
method A , having heated the
imine resulted in the presence of an acid for 4 hours gave compound 1-(2-chloro-8-
methylquinolin-3-yl)-2,3,4,9-tetrahydro-1
H -pyrido[3,4-b]indole (
4 ).
Method B: The
resulting imine was treated with NaBH
4
to give the amine
5 . The amine N-((2-chloro-8-
methylquinolin-3-yl)methyl)-2-(1
H -indol-3-yl)ethan-1-amine (
5 ) was reacted with
formaldehyde in an acidic medium (H
+
) to obtain 2-((2-chloro-8-methylquinolin-3-
yl)methyl)-2,3,4,9-tetrahydro-1
H -pyrido[3,4-b]indole (
