Учредитель – Федеральное государственное бюджетное образовательное учреждение
высшего профессионального образования «Южно-Уральский государственный
университет» (национальный исследовательский университет)
Журнал публикует рецензированные статьи по научным исследованиям, выполненным в различных
отраслях химической науки: неорганическая химия, органическая химия, аналитическая химия, физическая
химия и химия твёрдого тела. Приветствуется публикация статей по смежным отраслям. Редакционная
коллегия поддерживает высокий уровень публикаций, строго придерживаясь политики независимой
сторонней экспертизы, выполненной специалистами в соответствующей области, квалификация которых
подтверждена общепризнанными наукометрическими показателями.
Основной целью журнала является пропаганда актуальных научных исследований и содействие
формированию наиболее перспективных направлений.
Редакционная коллегия
д.х.н., проф. Шарутин В.В.
(отв. редактор);
д.х.н., проф. Авдин В.В.
(зам. отв. редактора);
к.х.н., доцент Мосунова Т.В.
(отв. секретарь);
д.х.н., проф. Ким Д.Г.
д.х.н., проф., чл.-корр. РАН Бамбуров В.Г.;
д.х.н., проф., чл.-корр. РАН Русинов В.Л.;
д.х.н., проф. Шарутина О.К.;
д.х.н., проф. Климов Е.С.;
д.х.н., проф. Гущин А.В.;
PhD, Full Professor (Spain) Garcia J.R.;
PhD (Spain) Khainakov S.A.
Стр.1
South Ural State University
The journal publishes peer-reviewed papers on scientific research in various branches of chemical science:
inorganic chemistry, organic chemistry, analytical chemistry, physical chemistry and solid-state chemistry. The
papers in related branches are welcome. The editorial board keeps the high quality of publications, strictly adhering
to the policy of independent third-party expert opinion, expressed by specialists in the corresponding branches,
whose qualification is confirmed by generally recognized scientometrical indicators.
The main aim of the journal is the promotion of actual scientific research and assistance in formation of the
most advanced directions.
Editorial board
V.V. Sharutin, Doctor of Science (Chemistry), Full Professor, South Ural State University,
Chelyabinsk, Russian Federation
V.V. Avdin, Doctor of Science (Chemistry), Full Professor, South Ural State University,
Chelyabinsk, Russian Federation
T.V. Mosunova, PhD (Chemistry), Associate professor, South Ural State University, Chelyabinsk,
Russian Federation
D.G. Kim, Doctor of Science (Chemistry), Full Professor, South Ural State University, Chelyabinsk,
Russian Federation
V.G. Bamburov, Doctor of Science (Chemistry), Full Professor, corresponding member of the
Russian Academy of Sciences, The Institute of Solid State Chemistry, Ekaterinburg, Russian
Federation
V.L. Rusinov, Doctor of Science (Chemistry), Full Professor, corresponding member of the Russian
Academy of Sciences, The Institute of Organic Synthesis, Ekaterinburg, Russian Federation
O.K. Sharutina, Doctor of Science (Chemistry), Full Professor, South Ural State University,
Chelyabinsk, Russian Federation
Е.S. Klimov, Doctor of Science (Chemistry), Full Professor, Ulyanovsk State Technical University,
Ulyanovsk, Russian Federation
A.V. Gushchin, Doctor of Science (Chemistry), Full Professor, Lobachevsky State University of
Nizhny Novgorod, Nizhny Novgorod, Russian Federation
J.R. García, PhD, Full Professor, University of Oviedo, Oviedo, Spain
S.A. Khainakov, PhD, Researcher, University of Oviedo, Mieres, Spain
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СONTENTS
Organic Chemistry
TARASOVA N.М., KIM D.G. Synthesis and halocyclization of allyl derivatives of 4,5dihydro-1,3-thiazol-2-thione
............................................................................................................ 4
SHARUTIN V.V., SHARUTINA O.K., SENCHURIN V.S., IL'CHENKO I.A. Synthesis
and structure of palladium complex [Ph3PCH=CHPPh3]2+[PdBr3(DMSO)]
2∙DMSO ........... 11
SHARUTIN V.V., SHARUTINAO.K., ARTEM'EVA E.V., MAKEROVA M.S. Reactions
of tri(ortho-tolyl)- and tri(meta-tolyl)antimony with oximes in the presence of an
oxidant. The structures of tri(ortho-tolyl)- and tri(meta-tolyl)antimony dioximates .............. 17
Analytical Chemistry
KRUPNOVA T.G., MASHKOVA I.V., KOSTRYUKOVA A.M., SCALEV E.D. The
study of groundwater quality of scientific and production center of the South forestry
in Ilmensky State Reserve ............................................................................................................... 27
Physical Chemistry
KOROLEVA O.N., MOSUNOVA T.V. Structure of lithium pyrosilicate melts according
to data of high-temperature Raman spectroscopy ........................................................................ 33
GRUBA O.N., GERMANYUK N.V., RYABUKHIN A.G. Formation (decomposition)
enthalpy calculations for crystal lattices of alkaline-earth fluorides ......................................... 39
MATVEYCHUK YU.V., ILKAEVA M.V., KRIVTSOV I.V., BARTASHEVICH E.V.
Comparative analysis of theoretical and experimental UV-spectra
of 2- and 8-thioquinoline ................................................................................................................. 45
© Издательский центр ЮУрГУ, 2015
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Organic Chemistry
SYNTHESIS AND HALOCYCLIZATION OF ALLYL DERIVATIVES
OF 4,5-DIHYDRO-1,3-THIAZOL-2-THIONE
N.М. Tarasova, South Ural State University, Chelyabinsk, Russian Federation,
nuts08@mail.ru
D.G. Kim, South Ural State University, Chelyabinsk, Russian Federation, kim_dg48@mail.ru
2-Propenyl-(2-methyl-1-propenyl-, 2-butenylthio- and (3-methylbutenyl-)thio4,5dihydro-1,3-thiazoles
are synthesized by alkylation of 4,5-dihydro-1,3-thiazol2-thione. These
products were researched in halocyclization reactions with iodine and bromine.
3-(halomethyl)-2,3,5,6-tetrahydrothiazolo[2,3-b]thiazolium and 6-halo-3,5,6,7-tetrahydro-2Hthiazolo[2,3-b]thiazinium
halides were formed. The structure of all the synthesized
compounds was confirmed by 1H NMR and gas chromatography-mass spectrometry.
Keywords: 4,5-dihydro-1,3-thiazol-2-thione, 2-propenylthio-4,5-dihydrothiazol, 2-(2methyl-1-propenyl)thio-4,5-dihydrothiazol,
2-butenylthio-4,5-dihydrothiazol, 2-(3-methylbutenyl)thio-4,5-dihydrothiazol,
3-(halomethyl)-2,3,5,6-tetrahydrothiazolo[2,3-b]thiazolium
and 6-halo-3,5,6,7-tetrahydro-2H-thiazolo[2,3-b]thiazinium halides, gas chromatographymass
spectrometry, 1H NMR.
Introduction
Derivatives of 1,3-thiazoline have antimicrobial and antihelmintial activity, besides they are the
effective immunomodulatory agents [1–3]. 2-Propenylthio-4,5-dihydro-1,3-thiazole was synthesized
previously from alkyl derivatives of 4,5-dihydro-1,3-thiazol-2-thione (1, 1,3-thiazoline-2-thione) [4].
The aim of the present study is the synthesis of new S-alkenyl derivatives of 4,5-dihydro1,3-thiazol-2-thione
and the investigation of their halocyclization reactions.
Discussion of results
We have found that 4,5-dihydro-1,3-thiazol-2-thione reacts with 3-bromopropene (2а), 3-chloro-2methylpropene
(2b), 4-bromobutene (2c), 1-bromo-3-methyl-2-butene (2d) to give 2-propenylthio-4,5dihydrothiazole
(2-allylthio-1,3-thiazoline) (3а), 2-(2-methyl-1-propenyl)thio-4,5-dihydrothiazole (3b),
2-butenylthio-4,5-dihydrothiazole (3c), 2-(3-methylbutenyl)thio-4,5-dihydrothiazole (3d) respectively
(scheme 1). Compounds 3а–d have been synthesized after treatment in ethanol with sodium ethylate as a
base. Note that in similar conditions the mixture of 2-(2-methyl-2-propenyl)thio-5-methyl-1,3,4thiadiazole
with 2-(2-methyl-1-propenyl)thio-5-methyl-1,3,4-thiadiazole at the ratio 1:2 have been
obtained from 5-methyl-1,3,4-thiadiazole-2-thione and methallylchloride 2b [5]. In this case the yield of
compound 3b is 62%.
2a BrCH2CH=CH2; 2b ClCH2C(CH3)=CH2; 2c BrCH2CH2CH=CH2; 2d BrCH2CH=C(CH3)2
Scheme 1. The alkylation of 4,5-dihydro-1,3-thiazol-2-thione
There is the molecular ion peak in the mass spectra (table 1, scheme 2, 3, 4) of compounds 3a–d.
The fragmentation processes with the elimination of methyl radical and the formation of the stable thiazolo-thiazolium
system for compounds 3а, b (scheme 2), as well as the formation of the thiazolothiazinium
system for compounds 3с, d (scheme 3, 4), are characteristic for all compounds. The peak
4
Bulletin of the South Ural State University. Ser. Chemistry.
2015, vol. 7, no. 2, pp. 4–10
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