Poster presentation
241
CATALYTIC SYNTHESIS OF 1,4-DISUBSTITUTED
1,2,3-TRIAZOLES BASED ON ORTHO-
PROPARGYLOXYBENZALDEHYDE AND SOME AROMATIC
AZIDES
I.S. Ortikov
1
, I.A. Abdugafurov
2
, B.Zh. Elmuradov
1
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.
e-mail: ortikovilxomjon@gmail.com
Nowadays, one of the important task is targeted synthesis of promising substances
based on the reaction of potentially active heterocyclic compounds, especially five- and
six-membered ring substances containing two or more heteroatoms, with electrophilic
and nucleophilic reagents and creating effective biologically
active drugs based on
them. In particular, scientific research is being carried out on obtaining new derivatives
of 1,2,3-triazoles using modern organic synthesis methods.
It is known that organic azides undergo a 1,3-bipolar cycloaddition reaction with
substances containing triple bonds and form a 1,2,3-triazole ring. It was discovered by
M. Meldal and B. Sharpless a catalytic method of cyclization, which today is called as
“click chemistry”. Scientists received the Nobel Prize in 2001 and 2022 for this
research. The fact that the authors were awarded 2 times for the method of azide-alkyne
cycloaddition shows that there is a high interest in this direction [1-3].
We started our research by alkylating salicylaldehyde with propargyl bromide and
synthesized the corresponding ortho-propargyloxybenzaldehyde (1).
It was studied the
cyclization reaction of 1 with 4-nitrophenylazide, 2-methyl-4-nitrophenylazide, 2-
bromo-4-nitrophenylazide (
2-4
). Experiments were carried out in the presence of
catalysts Cu(AcO)
2
and sodium ascorbate (SAA) in the ratio:
n
-PrOH : H
2
O (3:1).
The progress of the reaction was monitored by TLC and the optimal conditions for
the formation of 1,2,3-triazoles were determined. The structure of the obtained triazole
derivatives (
5-7
) was confirmed by IR and
1
H NMR spectra.
Compounds, consisting
formyl group can serve as synthons for further researches.
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