ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ
Bromo-chalcone with containing thiene ring by the reaction of selective dehydrobromination of α, β-dibromo ketone at presences of different amines in benzene solution and α-ethoxy-β-bromo-ketone in ethanolic solution in good yields were prepared. α, β-Dibromo ketone with the reaction of thiosem...
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2021
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Репозитарії
Ukrainian Chemistry Journal| _version_ | 1871465670143639552 |
|---|---|
| author | Mamedov, Ibrahim Shikhaliyeva, Irada Mamedova, Yegana |
| author_facet | Mamedov, Ibrahim Shikhaliyeva, Irada Mamedova, Yegana |
| author_institution_txt_mv | [
{
"author": "Ibrahim Mamedov",
"institution": "Baku State University, Faculty of Chemistry, Head of the department of Oil chemistry and chemical technology, professor"
},
{
"author": "Irada Shikhaliyeva",
"institution": "Baku State University, Faculty of Chemistry, department of Oil chemistry and chemical technology, researcher"
},
{
"author": "Yegana Mamedova",
"institution": "Baku State University, Faculty of Chemistry, department of Oil chemistry and chemical technology, researcher,"
}
] |
| author_sort | Mamedov, Ibrahim |
| baseUrl_str | https://ucj.org.ua/index.php/journal/oai |
| collection | OJS |
| datestamp_date | 2026-07-22T08:23:45Z |
| description | Bromo-chalcone with containing thiene ring by the reaction of selective dehydrobromination of α, β-dibromo ketone at presences of different amines in benzene solution and α-ethoxy-β-bromo-ketone in ethanolic solution in good yields were prepared. α, β-Dibromo ketone with the reaction of thiosemicarbazide lead to the formation of new pyrazole derivative. |
| doi_str_mv | 10.33609/2708-129X.87.01.2021.51-58 |
| first_indexed | 2025-09-24T17:43:37Z |
| format | Article |
| fulltext |
51
UDC 547 56 +544.72 doi: 10.33609/2708-129X.87.01.2021.51-58
STUDYING THE REACTION ROUTE OF α, β-DIBROMO KETONE
AT PRESENCES OF SOME AMINES
I. G. Mamedova*, I. M. Shikhaliyevaa, Y. V. Mamedovaa
aBaku State University, Faculty of Chemistry, akad. Z. Khalilov street 23, Baku, Azerbaijan,
bsu.nmrlab@mail.ru
α-Bromo-chalcone with containing thiene ring by the reaction of selective dehydro
bromination of α, β-dibromo ketone at presences of different amines in benzene solution and
α-ethoxy-β-bromo-ketone in ethanolic solution in good yields were prepared. α, β-Dibromo
ketone with the reaction of thiosemicarbazide lead to the formation of new pyrazole deriva‑
tive.
Keywords: acetophenone, chalcone, α, β-dibromo ketone, pyrazole.
İNTRODUCTION. The acetophenones,
their chalcone, α, β-dibromo ketone deriva‑
tives are important compounds in chemistry
and are valuable synthetic building blocks in
synthesis of various heterocyclic compounds.
α, β-Dibromo ketones are useful synthons in
the synthesis of a large number of pyrazolines,
pyrazolines, isoxazoles etc [1–11].
Due to their different functionality these
compounds confer biological activities, such
as antimicrobial, antibacterial, antifungal, an‑
ticancer, antitubercular, antiviral, antiinflam
matory, antihyperglycemic, and etc [12–17].
This work the reaction route of α, β-dibro‑
mo ketone at the presence of some amines had
been studied.
EXPERIMENT AND DISCUSSION OF RE-
SULTS. All the chemicals were obtained from
commercial sources (Aldrich) and used as re‑
ceived.
NMR experiments have been performed on
a BRUKER FT NMR spectrometer (UltraShi
eldTM Magnet) AVANCE 300 (300.130 MHz
for 1H and 75.468 MHz for 13C) with a BVT
3200 variable temperature unit in 5 mm sam‑
ple tubes using Bruker Standard software
(TopSpin 3.1). The 1H and 13C chemical shifts
were referenced to internal tetramethylsilane
(TMS); the experimental parameters for 1H:
digital resolution = 0.23 Hz, SWH = 7530 Hz,
TD = 32 K, SI = 16 K, 900 pulse-length = 10 μs,
PL1 = 3 dB, ns = 1, ds = 0, d1 =1 s; for 13C:
digital resolution = 0.27 Hz, SWH = 17985 Hz,
TD = 64 K, SI = 32 K, 900 pulse-length = 9 μs,
PL1 = 1.5 dB, ns = 100, ds = 2, d1 = 3 s (Figure
S1-S5). NMR-grade DMSO-d6 (99.7 %, con‑
taining 0.3% H2O) and CDCl3 were used for
the solutions of 3–7.
The purity of the synthesized compounds
was confirmed by thin-layer chromatography
ORGANIC CHEMISTRY STUDYING THE REACTION ROUTE OF α, β- DIBROMO KETONE AT PRESENCES OF SOME AMINES
52 ISSN 2708-129X. Укр. хім. журн., 2021
(TLC) on commercial aluminum-backed
plates of silica gel (60 F254), iodine vapor was
used as visualizing agent, eluent- 5:2 hexane/
ethyl acetate.
Melting points were measured on an Elec‑
trothermal 9100 apparatus without correction.
The procedure for syntheses of chalcone
To a solution of thiophene-2-carboxalde‑
hyde (1) (5 mmol) and 4-bromoacetophenone
(2) (5 mmol) in EtOH (20 ml), an aqueous
solution of sodium hydroxide (NaOH) (5%,
5 ml) was added. The temperature was kept at
25 ℃ and the mixture was stirred vigorously
for 3–4 h. Then, it was neutralized with aqque‑
ous HCl. The mixture was added to 50 g ice.
The solid product was separated by filtration
and the residue purified by crystallization from
mixture of carbon-4-chloride and hexane 1:1.
(E)-1-(4-Bromophenyl)-3-(thien-2-yl)prop-
2-en-1-one (3). Yellow crystals, yield 87%,
mp 133–135 ℃ [10].
The procedure for syntheses of α,β-dibromo
ketone
To a stirred solution of chalcone (3) 5 mmol)
in 25 ml of CH2Cl2 was added solution of bro‑
mine (5 mmol) in 5 ml of CH2Cl2 at 25 ℃. The
mixture was stirred for 1-2 h at room tempera‑
ture. The solid product was separated by filtra‑
tion and purified by crystallization from a mix‑
ture of of carbon-4-chloride and hexane 1:1.
2,3-Dibromo-1-(4-bromophenyl)-3-(thio-
phen-2-yl)propan-1-one (4). Colorless crystals,
yield, 77%, mp 138–139 ℃ [11].
The procedure for syntheses of α-ethoxy-β-
bromo-ketone and α-bromo chalcone
a) To a solution of dibromo chalcone (4)
(1 mmol) in CH3CH2OH (20 ml) was added
triethylamine (1 mmol) and ethylenediamine
(1 mmol). The mixture was stirred at the reflux
temperature of ethanol for 3 h. After comple‑
tion of the reaction, the mixture was added to
50 g ice, the solid product was separated by fil‑
tration and the residue purified by crystalliza‑
tion from a mixture of carbon-4-chloride and
hexane 1:1.
(2E)-2-bromo-1-(4-bromophenyl)-3-ethoxy-
3-(thiophen-2-yl)prop-2-en-1-one (5). Yellow
crystals, yield 87%, mp 165–168 ℃ (diastereo
mic mixture). 1H NMR (CDCl3, 300 MHz): δH
6.89-7.3 (3H, m, C4H3S), 7.56 and 7.9 (4H, d,
C6H4, J 9.0 Hz), 5.24 (1H, d, J 9.0 Hz, CH), 5.09
(1H, d, J 9.0 Hz, CH), 3.50 (2H, k, J 6.0 Hz,
CH2), 1.04 (3H, t, J 6.0 Hz, CH3). 13C NMR
(CDCl3, 75 MHz): δC 191.55, 133.33, 132.16,
131.86, 130.07, 129.08, 127.78, 126.59, 126.08,
65.41, 48.02, 14.99.
1H NMR (CDCl3, 300 MHz): δH 6.89-7.3
(3H, m, C4H3S), 7.56 and 7.66 (4H, d, C6H4),
5.34 (1H, d, J 9.0 Hz, CH), 5.18 (1H, d, J 9.0 Hz,
CH), 3.50 (2H, k, J 6.0 Hz, CH2), 1.29 (3H, t, J
6.0 Hz, CH3). 13C NMR (CDCl3, 75 MHz): δC
192.02, 133.90, 132.16, 131.96, 130.34, 129.23,
128.06, 127.05, 126.13, 65.89, 49.28, 15.03.
b) To a solution of dibromo chalcone (4)
(1 mmol) in benzene (20 ml) was added tri‑
ethylamine (1 mmol) and ethylenediamine
(1 mmol). The mixture was stirred at the reflux
temperature of benzene for 3 h. After complet‑
ed of reaction the mixture was added to 50 g
ice, the solid product was separated by filtra‑
tion and the residue purified by crystallization
from a mixture of carbon-4-chloride and he
xane 1:1.
(Z)-2-bromo-1-(4-methylphenyl)-3-(thio-
phen-2-yl)prop-2-en-1-one (6). Yellow crystals,
yield 77%, mp 173 ℃. 1H NMR (DMSO-d6,
300 MHz). δH 8.26 (1H, s, =CH), 8.04 (1H, d,
J 6.0 Hz, CH), 7.83 (1H, d, J 6.0 Hz, CH), 7.76
(2H, d, J 8.2 Hz, arom.), 7.67 (2H, d, J 8.2 Hz,
arom.), 7.28 (1H, t, J 6.0 Hz, CH). 13C NMR
UCJ № 1 / Vol. 87I. G. Mamedov, I. M. Shikhaliyeva, Y. V. Mamedova
53https://ucj.org.ua
(CDCl3, 75 MHz). δC 189.86, 139.06, 138.46,
137.30, 136.22, 134.16, 132.22, 131.69, 128.24,
126.75, 119.51.
The procedure for syntheses of pyrazole
To a solution of dibromo chalcone (4)
(1 mmol) in CH3CH2OH (20 ml) was added
triethylamine (1 mmol) and thiosemicarbazide
(1 mmol). The mixture was stirred at the reflux
temperature of ethanol for 3 h. After comple‑
tion of the reaction, the mixture was added to
50 g ice, the solid product was separated by fil‑
tration and the residue purified by crystalliza‑
tion from a mixture of carbon-4-chloride and
hexane 1:1.
3-(4-bromophenyl)-5-(thiophen-2-yl)-1H-
pyrazole-1-carbothioamide (7). Colorless crys‑
tals, yield 63%, mp 188 ℃. 1H NMR (DM‑
SO-d6, 300 MHz). δH 8.04 (2H, d, J 8.2 Hz,
arom.), 7.94 (1H, d, J 15.0 Hz, NH), 7.82 (1H,
d, J 6.0 Hz, CH), 7.77 (2H, d, J=8.2 Hz, arom.),
7.76 (1H, t, J 6.0 Hz, CH), 7.71 (1H, d, J 6.0 Hz,
CH), 7.55 (1H, d, J 15.0 Hz, NH), 7.20 (1H,
=CH).
DISCUSSION OF THE RESULTS. Firstly,
the chalcone derivatives 3 and 4 were synthe‑
sized by using literature methods [10, 11]. As a
result of the reactions of the thiophene-2-car‑
boxaldehyde 1 with 4-bromoacetophenone 2
in ethanolic NaOH were obtained chalcone
derivative 3 with good yield. Brominating of
thienyl chalcone (3) with bromine in CH2Cl2 at
room temperature resulted in selective forma‑
tion of the α, β-dibromo chalcone derivative 4.
Despite that thiene ring is sensitive to electro‑
philic substitution at its 4 and 5 positions, the
brominated product of the thiene ring doesn’t
detect in this reaction (Scheme).
Scheme. The synthesis route of compounds 37
ORGANIC CHEMISTRY STUDYING THE REACTION ROUTE OF α, β- DIBROMO KETONE AT PRESENCES OF SOME AMINES
54 ISSN 2708-129X. Укр. хім. журн., 2021
The structures of known compounds (3 and
4) were established based on spectral data and
comparison with literature data [10, 11].
At next stage of this work, the reaction of α,
β-dibromo ketone 4 with equivalence amount
of triethylamine, ethylenediamine mixture in
refluxing temperature of ethanol and benzene
have been carried out. In ethanolic solution
interaction of solvent with the α, β-dibromo
ketone gave to α-ethoxy-β-bromo-ketone 5
(fig. 1 and 2), in benzene solution the forma‑
tion of regioselective α-bromo-chalcone 6 ob‑
served (fig. 3 and 4). It is important to note, the
presences of asymmetric centers in the compo
und of 5 lead to a doubling of the signals in 1H,
13C spectra, which it is very interesting in terms
of NMR spectroscopy (fig. 1 and 2).
At the final stage of this study, the reaction
of α, β-dibromo ketone 4 with equivalence
amount of triethylamine, thiosemicarbazone
mixture in refluxing temperature of ethanol
(or benzene) lead to new pyrazole derivative 7
(fig. 5).
The formation of pyrazole derivatives by
refluxing of α, β-dibromo ketone 4 with the
phenyl hydrazine or 2,4-dinitrophenylhydra‑
zine in ethanolic and benzene solutions wasn’t
observed.
Fig. 1. 1H NMR contour plot of 5 in CDCl3.
UCJ № 1 / Vol. 87I. G. Mamedov, I. M. Shikhaliyeva, Y. V. Mamedova
55https://ucj.org.ua
Fig. 2. 13C NMR contour plot of 5 in CDCl3.
Fig. 3. 1H NMR contour plot of 6 in DMSO-d6.
ORGANIC CHEMISTRY STUDYING THE REACTION ROUTE OF α, β- DIBROMO KETONE AT PRESENCES OF SOME AMINES
56 ISSN 2708-129X. Укр. хім. журн., 2021
Fig. 4. 13C NMR contour plot of 6 in DMSO-d6.
Fig. 5. 1H NMR contour plot of 7 in DMSO-d6.
UCJ № 1 / Vol. 87I. G. Mamedov, I. M. Shikhaliyeva, Y. V. Mamedova
57https://ucj.org.ua
CONCLUSİONS. In summary, a new α-eth‑
oxy-β-bromo-ketone, α-bromo chalcone and
pyrazole derivatives have been prepared in
good yields by the reactions of α, β-dibromo
ketone with triethylamine, ethylenediamine or
triethylamine thiosemicarbazone mixture in
different reaction conditions.
We would like to note that the reported re‑
sults have never been presented before.
ВИВЧЕННЯ РЕАКЦІЇ α, β-ДИБРОМКЕТОНУ В
ПРИСУТНІСТІ ДЕЯКИХ АМІНІВ
І. Г. Мамедов а*, І. М. Шихалієва а,
Ю. В. Мамедова
Бакинський державний університет, хіміч-
ний факультет, вул. Акад. З. Халілова 23,
Баку, Азербайджан
У результаті реакцій α, β-дибромкетону з
сумішшю триетиламіну, етилендіаміну або
триетиламіну тіосемікарбазону за різними
реакційними умовами було отримано з доб
рими виходами нові α-етокси-β-бромоке‑
тон, α-бромхалкон та похідні піразолу. Се‑
лективна реакція дегідробімування α, β-ди‑
бромкетону в присутності різних амінів у
розчині бензолу та α-етокси-β-бром-кетону
в етанолі дозволила отримати значну кіль‑
кість α-бром-халкону зі вмістом тієнового
кільця. Методами ЯМР встановлено, що
реакція α, β-дибромкетону з тіосемікарба‑
зидом призводить до утворення нового по‑
хідного піразолу.
Ключові слова: ацетофенон, халкон,
α, β-дибромкетон, піразол.
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Стаття надійшла 05.02.2020.
|
| id | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-274 |
| institution | Ukrainian Chemistry Journal |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2026-07-23T01:05:43Z |
| publishDate | 2021 |
| publisher | V.I.Vernadsky Institute of General and Inorganic Chemistry |
| record_format | ojs |
| resource_txt_mv | ucjorgua/8e/b2583ad499c5f86e8a955cb1c5c4b98e.pdf |
| spelling | oai:ojs2.1444248.nisspano.web.hosting-test.net:article-2742026-07-22T08:23:45Z STUDYING THE REACTION ROUTE OF α, β-DIBROMO KETONE AT PRESENCES OF SOME AMINES ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ Mamedov, Ibrahim Shikhaliyeva, Irada Mamedova, Yegana acetophenone, chalcone, α, β-dibromo ketone, pyrazole. Bromo-chalcone with containing thiene ring by the reaction of selective dehydrobromination of α, β-dibromo ketone at presences of different amines in benzene solution and α-ethoxy-β-bromo-ketone in ethanolic solution in good yields were prepared. α, β-Dibromo ketone with the reaction of thiosemicarbazide lead to the formation of new pyrazole derivative. V.I.Vernadsky Institute of General and Inorganic Chemistry 2021-02-19 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/274 10.33609/2708-129X.87.01.2021.51-58 Ukrainian Chemistry Journal; Vol. 87 No. 1 (2021): Ukrainian Chemistry Journal; 51-58 Украинский химический журнал; ##issue.vol## 87 ##issue.no## 1 (2021): Украинский химический журнал; 51-58 Український хімічний журнал; Том 87 № 1 (2021): Український хімічний журнал; 51-58 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/274/152 Copyright (c) 2021 Ibrahim Mamedov, Irada Shikhaliyeva, Yegana Mamedova https://creativecommons.org/licenses/by-nc/4.0 |
| spellingShingle | Mamedov, Ibrahim Shikhaliyeva, Irada Mamedova, Yegana ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ |
| title | ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ |
| title_alt | STUDYING THE REACTION ROUTE OF α, β-DIBROMO KETONE AT PRESENCES OF SOME AMINES |
| title_full | ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ |
| title_fullStr | ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ |
| title_full_unstemmed | ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ |
| title_short | ЕЛЕКТРОХРОМНІ ВЛАСТИВОСТІ ВОЛЬФРАМАТІВ ВІСМУТУ ТА НІКЕЛЮ |
| title_sort | електрохромні властивості вольфраматів вісмуту та нікелю |
| topic_facet | acetophenone chalcone α β-dibromo ketone pyrazole. |
| url | https://ucj.org.ua/index.php/journal/article/view/274 |
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