YU-ISSN 0352-5139
J. Serb. Chem. Soc. Vol. 66 No. 1 (2001)
CONTENTS
Organic Chemistry
P. Had`i}, N. Vukojevi}, M. Popsavin and J. ^anadi: Nucleophilic opening of the 3,5-anhydro ring in 1,2O-cyclohexylidene-a-D-xylofuranose
1
E. Comanita, G. Roman, I. Popovici and B. Comanita: Synthesis and reactivity of some Mannich bases.
VIII. Studies on several Mannich bases derived from ortho-hydroxyacetophenones and their conversion
into oximino derivatives
9
R.A. El-Sayed: Sulfur containig activated hydantoins. Synthesis and screening some novel
benzylidenehydantoins amino acids derivatives
17
S. Stojanovi}, D. Molnár Gabór, Lj. Medi}-Mija~evi}, M. Saka~ and K. Penov Ga{i: Synthesis and
chemical behaviour of 17a-butyl-3b,17b-dihydroxy-16-oximino-5-androstene (Note)
23
Electrochemistry
A. Buzarovska, I. Arsova and Lj. Arsov: Electrochemical synthesis of poly(2-methyl aniline):
Electrochemical and spectroscopic characterization
27
Analytical Chemistry
M. B. Aleksi}, D. G. Agbaba, R. M. Bao{i}, D. M. Milojkovi}-Opsenica and @. Lj. Te{i}: Thin-layer
chromatography of several antihypertensive drugs from the group of angiotensin converting enzyme
inhibitors
39
N. Petrovi}, D. Budjelan, S. Coki} and B. Ne{i}: The determination of the content of gold and silver in
geological samples
45
Chemical Engineering
S. M. [erbula and V. D. Stankovi}: Hydrodynamic characteristics of a two-phase gas-liquid flow upward
through a fixed bed of spherical particles
53
J. Serb. Chem. Soc. 66(1)1–8(2001)
UDC 547.424.1:547.737
JSCS – 2824
Original scientific paper
Nucleophilic opening of the 3,5-anhydro ring in 1,2-O-cyclohexylidene-a-D-xylofuranose
PAVLE HAD@I]a, , NADA VUKOJEVI]b, MIRJANA POPSAVINa and JANO[ ^ANADIa#
aInstitute of Chemistry, Faculty of Science, University of Novi Sad, Trg Dositeja Obradovi}a 3, YU-21000
Novi Sad and bDepartment of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode
Stepe 450, YU-11000 Belgrade, Yugoslavia
(Received 23 May 2000)
The reactivity of the oxetane ring in 3,5-anhydro-1,2-O-cyclohexylidene-a-D-xylofuranose (1) was
exemplified by its regiospecific nucleophilic opening. The action of concentrated hydrobromic or
hydroiodic acid on 1 resulted in the exclusive formation of the 5-deoxy-5-halo derivatives, while the action
of acetyl chloride or acetyl bromide yielded the corresponding 3-O-acetyl-5-deoxy-5-halo derivatives in 70
– 90 % yield. Under strongly acidic reaction conditions, the protection of the cyclohexylidene acetal
function remained intact.
Keywords: oxetane, sulfonyl esters, nucleophilic ring opening, D-xylofuranose derivatives.
REFERENCES
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J. Serb. Chem. Soc. 66(1)9–16(2001)
UDC 547.427.2:547.388.1
JSCS – 2825
Original scientific paper
Synthesis and reactivity of some Mannich bases. VIII. Studies on several Mannich bases derived from
ortho-hidroxyacetophenones and their conversion into oximino derivatives
EUGENIA COMANITA1, GHEORGHE ROMAN2, IRINA POPOVICI3 and
BOGDAN COMANITA4
1Department of Organic Chemistry, "Gh. Asachi" Technical University, 71A D. Mangeron Blvd., RO-6600
Iasi, Romania, 2Chemistry Department, "Transilvania" University, 29 Eroilor Blvd., RO-2200 Brasov,
Romania, 3"Gr. T. Popa" University of Medicine and Pharmacy, 16 University St., RO-6600 Iasi, Romania
and 4National Research Council of Canada, Institute for Chemical Process and Environmental Technology,
Montreal Road Campus, KIA 0R6, Ottawa, Canada
(Received 22 December 1999)
The synthesis of several Mannich bases resulting from the reaction of 2-hydroxy-4-methylacetophenone
with paraformaldehyde and secondary amines is reported. Another series of products was obtained from
N,N-dimethyl substituted Mannich bases by replacing the amino group with pyrrolidine. Most of the
Mannich bases were transformed into oximes by treatment with hydroxylamine hydrochloride in 10 %
NaOH.
Keywords: ortho-phenolic ketones, Mannich bases, amine exchange reaction, Mannich bases oximes.
REFERENCES
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18. D. M. Fink, B. A. Kurys, Tetrahedron Lett. 37 (1996) 995 and references cited therein.
J. Serb. Chem. Soc. 66(1)17–21(2001)
UDC 547.622:547.78:547.466
JSCS – 2826
Original scientific paper
Sulfur containing activated hydantions.
Synthesis and screening some novel benzylidenehydantoins amino acids derivatives
RAGAB A. EL-SAYED
Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
(Received 19 September 1999, revised 7 May 2000)
5-Benzylidenehydantoin reacts with chlorosulfonic acid to give the corresponding p-sulfonyl chloride 1.
Condensation with nucleophiles gives amino acid derivatives 2–7. Coupling reactions of some amino acid
derivatives (2–6) with amino acid methyl ester hydrochloride in THF-Et3N medium using the
dicyclohexylcarbodiimide method (DCC) furnish the desired dipeptide methyl esters 8–12. The spectral
data of the synthesized compounds are briefly discussed.
Keywords: benzylidenehydantoins amino acids, dipeptide derivatives.
REFERENCES
1. R. A. El-Sayed, J. Serb. Chem. Soc. 56 (1991) 311
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J. Serb. Chem. Soc. 66(1)23–26(2001)
UDC 615.35:547.388.4:
JSCS–2827
Note
NOTE
Synthesis and chemical behaviour of 17a-butyl-3b,17b-dihydroxy-16-oximino-5-androstene
SRDJAN STOJANOVI]#, DORA MOLNÁR GÁBOR#, LJUBICA MEDI]-MIJA^EVI]#, MARIJA
SAKA^# and KATARINA PENOV GA[I#
Institute of Chemistry, Faculty of Science, Trg Dositeja Obradovi}a 3, YU-21000 Novi Sad,
Yugoslavia
(Received 4 July, revised 13 October 2000)
Starting from 3b-hydroxy-16-oximino-5-androsten-17-one (1), the recently synthesized 16-oximino-17bhydroxy-17a-butyl derivative 2 gave by the Beckmann fragmentation reaction with titanium(III) chloride or
p-toluenesulphonyl chloride the corresponding D-seco derivative 3. However, using acetic anhydride, in
addition to the 3b-acetoxy D-seco derivative 4, the 17-aza D-homo derivative 5 was obtained. The structure
of compound 5 was proposed on the basis of NMR-spectroscopy.
Keywords: 17-aza-D-homo derivatives of androstene, Beckmann fragmentation.
REFERENCES AND NOTE
1. D. Miljkovi}, K. Penov Ga{i, E. Djurendi}, M. Saka~, Lj. Medi}-Mija~evi}, V. Pejanovi}, S. Stankovi},
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2. IR spectra (wave numbers in cm–1) were recorded using a Perkin-Elmer 457 spectrometer as KBr discs
or films. The 1H and 13C-NMR spectra were recorded using a Bruker AC 250E instrument, with
tetramethylsilane as the internal standard. The chemical shifts are given in ppm (d-scale). The melting point
were determined with a Buchi SMP-20 apparatus and are not corrected.
3. R. D. H. Heard, M. T. Ryan, H. I. Bolker, J. Org. Chem. 24 (1959) 172.
J. Serb. Chem. Soc. 66(1)27–37(2001)
UDC 547..551:542.9:541.138
JSCS – 2828
Original scientific paper
Electrochemical synthesis of poly(2-methyl aniline): electrochemical and spectroscopic characterization
ALEKSANDRA BUZAROVSKA, IRENA ARSOVA and LJUBOMIR ARSOV
Faculty of Technology and Metallurgy, University “St. Cyril and Methodius”, 91000 Skopje,
Macedonia
(Received 21 June, revised 31 October 2000)
Poly(2-methyl aniline) or poly(ortho-toluidine), as ring substituted derivative of aniline, has been
synthesized electrochemically in various concentrations of H2SO4 and HCl, and then characterized by
cyclic voltammetry, as well as by impedance and Raman spectroscopy. The cyclic voltammograms of
poly(o-toluidine) and poly(aniline) show that the electrochemical polymerization of these two polymers
proceeds by almost identical mechanisms. The Raman spectroscopical measurements suggest that the redox
reactions of poly(aniline) and poly(o-toluidine) are similar in the potential range between –0.2 and 0.7 V
vs. SCE. The impedance measurements showed that the conductivity of poly(o-toluidine) is an order of
magnitude lower than that of the corresponding poly(aniline) form.
Keywords: poly(2-methyl aniline), electropolymerization, cyclic voltammetry, Raman spectroscopy.
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J. Serb. Chem. Soc. 66(1)39–44(2001)
UDC 549.284–002.4:543.544
JSCS – 2829
Original scientific paper
Thin-layer chromatography of several antihypertensive drugs from the group of angiotensin converting
enzyme inhibitors
MIRJANA B. ALEKSI],1 DANICA G. AGBABA,1 RADA M. BAO[I],2
DU[ANKA M. MILOJKOVI]-OPSENICA2# and @IVOSLAV LJ. TE[I]2#
1Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, P. O. Box 146, YU-11001
Belgrade and 2Faculty of Chemistry, University of Belgrade, Studentski trg 16, P. O. Box 158, YU-11001
Belgrade, Yugoslavia
(Received 3 April, revised 26 June 2000)
A rapid and simple method for the chromatographic separation of pharmacologically active components
contained in some antihypertensive drugs has been developed employing thin-layers of silica gel and
polyacrylonitrile sorbent (PANS). The active compounds of Captopril – (S)-1-(3-mercapto-2-methyl-1oxopropyl)-L-proline, Enalapril – (S)-1-[N- [1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline,
Lisinopril – (S) -1-[N2-(carboxy-3-phenylpropyl)-L-lysyl]-L-proline, Quinapril – [3S-[2[R*(R*)],3R*]], 2- [2-[[1(- etho- xycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-iso-quinolinecarboxylic acid, Ramipril – [2S-[1[R*(R*)],2a3ab,6ab]]-1-[2[[1-(ethoxycarbo- nyl)-3phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]-pyrole-2-carboxylic acid and Cilazapril – [1S[1a,9a (R*)]]- 9-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino] octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]
diazepine-1-carboxylic acid, were successfully separated by the presented procedures. For their
chromatographic separation on silica gel sixteen and on PANS thirteen solvents were used.
Keywords: thin-layer chromatography, silica gel, polyacrylonitrile sorbent, antihypertensive drugs,
angiotensin converting enzyme inhibitors.
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J. Serb. Chem. Soc. 66(1)45–52(2001)
UDC 549.282:549.283:543.062:620.11
JSCS – 2830
Original scientific paper
The determination of the content of gold and silver in geological samples
N. PETROVI], D. BU\ELAN,# S. COKI] and B. NE[I]#
Copper Institute, Zeleni bulevar 35, YU-19210 Bor, Yugoslavia
(Received 5 March, revised 15 September 2000)
A method has been elaborated for the determination of the content of gold and silver in geological samples
by atomic absorption spectrophotometry (AAS) in combination with the fire assay method. The weight of
sample used for analysis was 10 g. Sulphur present as sulphide, which is an undesirable element in
smelting, was removed by the addition of iron to the charge. The sample was smelted with fluxes and lead
oxide to replace the silver and gold by lead and to transfer non-precious elements to slag. Lead was
separated from precious metals by cupellation. The separated silver and gold alloy was dissolved with aqua
regia with addition of hydrochloric acid in excess. Silver and gold were determined from the same solution.
For determination of the silver content, the AAS method with an air-acetylene flame was used. Gold was
determined in a graphite furnace with the addition of a matrix modifier in an argon current, at an
atomization temperature of t = 2200 ºC. The lower determination limit for silver was 0.05 g/t and for gold
0.005 g/t. The results of the analysis for silver and gold obtained with the proposed method showed good
agreement with the results of the analysis of the same samples with the fire assay method.
Keywords: geological sample, gold, silver, fire assay, atomic absorption, air-acetylene flame, graphite
furnace.
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9. A. Golob, A. Kandi}, B. Ne{i}, Chimia 52 (1998) 414
10. A. Sporea, R. Radulescu, S. Petrescu, Chimia 52 (1998) 416.
J. Serb. Chem. Soc. 66(1)53–64(2001)
UDC 541.124:541.123.2
JSCS – 2831
Original scientific paper
Hydrodynamic characteristics of a two-phase gas-liquid flow
upward through a fixed bed of spherical particles
SNE@ANA M. [ERBULA and VELIZAR D. STANKOVI]#
Technical Faculty Bor, University of Belgrade, P. O. Box 50, YU-19210 Bor, Yugoslavia
(Received 17 January, revised 31 July 2000)
The influence of an electrochemically generated gas phase on the hydrodynamic characteristics of a threephase system has been examined. The two-phase fluid, (gas-liquid), in which the liquid phase is the
continuous one, flows through a packed bed with glass spheres. The influence of the liquid velocity was
examined, as well as the gas velocity and particle diameter on the pressure drop through the fixed bed. It
was found that with increasing liquid velocity (wl = 0.0162–0.03 m/s), the relative pressure drop decreases
through the fixed bed. With increasing current density, the pressure drop increases, since greater gas
quantities stay behind in the fixed bed. Besides, it was found that with decreasing diameter of the glass
particles, the relative pressure drop also decreases. The relationship betweeen the experimentally obtained
friction factor and the Reynolds number was established.
Keywords: two-phase flow, fixed bed, water electrolysis, pressure drop, fluidization.
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