СATALYTIC CYCLIZATION OF ISOMERIC BROMOAZIDES AND PROPARGYL ESTER I.S. Ortikov 1 , Sh.R. Khozhimatova 2 , B.J. 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 e-mail: ortikovilxomjon@gmail.com.
2) Andijan Institute of Mechanical Engineering, Andijan , Uzbekistan Among the heterocyclic pharmacologically active substances, triazole derivatives
stand out for their ease of synthesis, high biological activity, and low toxicity.
Currently, synthetically obtained biologically active substances occupy the main place
in pharmaceuticals and agriculture. According to the analysis of literature published in
recent years, among five-membered heterocyclic compounds, 1,2,3-triazole derivatives
have the highest biological activity [1-2].
Our research is also focused on the synthesis, chemical transformations and
biological activities of 1,2,3-triazole derivatives. For this, we use the azide-alkyne
cycloaddition reaction, which is the main synthesis method of 1,2,3-triazoles [3]. We
have chosen propargyl ester of monoiodoacetic acid as an object. First, the
corresponding propargyloacetate ester was synthesized from monoiodoacetic acid and
propargyl alcohol through an esterification reaction.
The resulting ether was alkylated with para-iodophenol and the corresponding prop-
2-yn-1-yl 2-(4-iodophenoxy)acetate (
1 ) was isolated. 1,3-Bipolar cycloaddition reaction
of this compound with
ortho-, meta - and
para- bromophenylazides was carried out by
refluxing a mixture of reagents in a ratio of 1:1 in the presence of a copper(I) bromide
catalyst in toluene for 6 hours:
The reaction mixture was cooled, the precipitate was filtered, dried, and its physical
constants were studied. The IR and
1
H NMR spectra of the substances obtained as a
result of catalytic ringing were analyzed. As a result, it was determined that 1,4-isomers
of 1H-1,2,3-triazole derivatives were formed (