503
Chemistry of Heterocyclic Compounds 2020, 56(5), 503–505
Aryltellurium trihalides in the synthesis of
heterocyclic compounds (microreview)
Mykola M. Kut*
1
, Mikhaylo Yu. Onysko
1
1
Uzhhorod National University,
46 Pidgirna St., Uzhhorod 88000, Ukraine; е-mail: kutmykola@ukr.net
Submitted March 11, 2020
Accepted April 10, 2020
Mykola M. Kut, Assistant, Department of Organic
Chemistry, Uzhhorod National University, Ukraine.
He defended his PhD thesis in 2019 at the Institute of
Organic Chemistry of the National Academy of
Sciences of Ukraine. His scientific interests include
the development of new methods for the synthesis of
nitrogen-containing heterocyclic compounds by
electrophilic cyclization, the chemistry of organic
derivatives of selenium and tellurium, and the
directed synthesis of biologically active compounds.
Mikhaylo Yu. Onysko, Associate Professor,
Department of Organic Chemistry, Uzhhorod
National University, Ukraine. He defended his PhD
thesis in 2001 at the Institute of Organic Chemistry
of the National Academy of Sciences of Ukraine.
His scientific interests include the development of
new methods for the synthesis of nitrogen-
containing heterocyclic compounds by electrophilic
cyclization, the chemistry of organic derivatives of
selenium and tellurium, and the directed synthesis
of biologically active compounds.
lides
11
in the reactions of electrophilic intramolecular
cyclization in the synthesis of mono- and polycyclic furan,
pyran, and thiazole derivatives.
Introduction
Aryltellurium trihalides are used as electrophilic reagents
in the synthesis of organotellurium compounds
1,2
with high
biological activity.
3–10
This microreview focuses on the use
of synthetically available p-alkoxyphenyltellurium triha-
The review is devoted to the methods of synthesis of furan, pyran, and thiazole
derivatives employing aryltellurium trihalides published in 1983–2019.
The reactions of aryltellurium trihalides with γ,δ-alkenyl
alcohols, carbonyl compounds, acids, and their derivatives
are the most studied. The reaction of p-alkoxy(alkyl)-
phenyltellurium trichlorides 1a,c,d with γ,δ-unsaturated
alcohols and ethers 2 in CHCl
3
allows the one-step synthe-
sis of tetrahydrofuran derivatives 3 with an exocyclic aryl-
telluriium fragment in 65–98% yields. The use of p-meth-
oxyphenyltellurium tribromide (1b) in the synthesis of tellu-
rium-functionalized furan reduces the yields of products 3.
12
Cyclization of sterically hindered alkenols with aryltellurium
trichlorides results in 2,3,5-substituted tetrahydrofurans in
high yields (85–98%).
13
The use of γ,δ-alkenols containing a
double carbon–carbon bond in the alicycles in reactions with
aryltellurium trihalides results in the annulation of the furan
ring and the formation of bicyclic furans.
12
The use of
alkenyl derivatives of glycols or dibenzyl esters allows the
preparation of 2,5-substituted tetrahydrofurans suitable for
further functionalization. The yields of cyclization products
of glycols reach 96%; the use of benzyl esters reduces the
yields of the target products to 65%.
13
Synthesis of furan derivatives
Benzotetrahydrofurans 5 are formed in high yields in the
reaction of p-methoxyphenyltellurium trichloride (1a) with
Published in Khimiya Geterotsiklicheskikh Soedinenii,
2020, 56(5), 503–505
0009-3122/20/56(5)-0503©2020 Springer Science+Business Media, LLC
DOI 10.1007/s10593-020-02688-3
2-allylcyclohexanol or o-allylphenols 4 in CHCl
3
.