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SYNTHESIS OF NOVEL HYBRIDE MOLECULES CONTAINING



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Abstracts ICPS 2023

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 (

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