The Influence of Condensed Cycle on Regiochemistry of Electrophilic Heterocyclization of 3-Alkenyl-2-Thioxopyrimidin-4-One by p-Alkoxyphenyltellurium Trichloride

Article abstract of DOI:10.1002/jhet.3114

Electrophilic heterocyclization of 5-alkenyl-1-methyl-6-thioxopyrazolo[3,4-d]pyrimidin-4-ones and 3-alkenyl-2-thioxoquinazoline-4-ones under the action of p-alkoxyphenyltellurium trichloride leads to annulation of thiazoline cycle with formation of 7-[(p-alkoxyphenyl)telluromethyl]-1-methyl-6,7-dihydropyrazolo[3,4-d][1,3]thiazolo[3,2-a]pyrimidin-4(1H)-ones hydrochlorides and 2-(p-alkoxyphenyl)dichlorotelluromethyl-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-ones hydrochlorides. Reduction of salts by the action of excess of sodium sulfite leads to formation of arylhetaryl telluride.

Full text of DOI:10.1002/jhet.3114

Month 2018
The Influence of Condensed Cycle on Regiochemistry of Electrophilic
Heterocyclization of 3-Alkenyl-2-Thioxopyrimidin-4-One by p-
Alkoxyphenyltellurium Trichloride
*
Mykola Kut, Mikhajlo Onysko,
and Vasil Lendel
Organic Synthesis Laboratory, Uzhhorod National University, Uzhhorod 88000, Ukraine
*
E-mail: muonysko@gmail.com
Received October 4, 2017
DOI 10.1002/jhet.3114
Published online 00 Month 2018 in Wiley Online Library (wileyonlinelibrary.com).
Electrophilic heterocyclization of 5-alkenyl-1-methyl-6-thioxopyrazolo[3,4-d]pyrimidin-4-ones and 3-
alkenyl-2-thioxoquinazoline-4-ones under the action of p-alkoxyphenyltellurium trichloride leads to annula-
tion of thiazoline cycle with formation of 7-[(p-alkoxyphenyl)telluromethyl]-1-methyl-6,7-
dihydropyrazolo[3,4-d][1,3]thiazolo[3,2-a]pyrimidin-4(1H)-ones hydrochlorides and 2-(p-alkoxyphenyl)
dichlorotelluromethyl-2,3-dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-ones hydrochlorides. Reduction of
salts by the action of excess of sodium sulfite leads to formation of arylhetaryl telluride.
J. Heterocyclic Chem., 00, 00 (2018).
INTRODUCTION
condensed cycle on 3-alkenyl-2-thioxopyrimidin-4-one
onto the regiochemistry of electrophilic action of the
aryltellurium trichlorides.
Reactions of electrophilic heterocyclization are widely
used for the synthesis of various heterocyclic polycyclic
systems [1–7]. Some resources describe the impact of
different factors (the nature of the electrophilic reagent,
the polarization of the alkenyl substituent, the
nucleophilicity of the exo-heteroatom or endocyclic
heteroatom, the nature of the condensed ring, and the
reaction conditions) on the regiochemistry of the process
of electrophilic intramolecular cyclization of alkenyl
derivatives of heterocycles [2,5,6,8]. Tellurium-containing
electrophiles in such reactions are not studied enough,
especially that the aryltellurium trichlorides are the most
perspective, because of high stability of corresponding
products of electrophilic heterocyclization [9–13]. There
are data [9–12] about usage of aryltellurium
trihalogenides in the reactions with unsaturated O-
nucleophiles, namely, their interaction with unsaturated
alcohols, phenols, and acids. Our previous investigation
of reactions of aryltellurium trihalogenides with
unsaturated mercapto-derivatives of N-alkenyl derivatives
RESULTS AND DISCUSSION
The 5-alkenyl-6-thioxo-1-methylpyrazolo[3,4-d]pyrimidin-
4-ones 1 and 2 have been used as model compounds for
the study of tellurocyclization; they were synthesized
from 5-amino-4-carbetoxy-1-methylpyrazole and the
corresponding alkenyl isothiocyanates by the Scheme 1.
Heterocyclization of 5-alkenyl-6-thioxo-1-methylpyrazolo
[3,4-d]pyrimidin-4-ones with the p-methoxyphenyltellurium
trichloride was carried out in acetic acid medium,
chloroform, acetonitrile at different temperatures. The
usage of acetic acid at the room temperature was found
as optimal conditions for cyclization. In results, the linear
polycyclic systems 3 and 4 with the salt-like structure
and exocyclic aryltellurium fragment were obtained
(Scheme 2). It is found that cyclization of 5-alkenyl-
6-thioxo-1-methylpyrazolo[3,4-d]pyrimidin-4-ones with
the p-methoxyphenyltellurium trichloride proceeds
regiospecifically with the formation of hydrochlorides
7-[dichloro(4-methoxyphenyl)-telluromethyl]-1-methyl-6,7-
5,6-disubstituted
2-thioxothieno[2,3-d]pyrimidin-4-one
was described in the paper [13]. Therefore, the aim of our
study is the investigation of the effect of nature of
© 2018 Wiley Periodicals, Inc.

M. Kut, M. Onysko, and V. Lendel
Vol 000
Scheme 1. Synthesis of 5-alkenyl-6-thioxo-1-methylpyrazolo[3,4-d]
pyrimidin-4-ones 1 and 2.
Scheme 3. Synthesis of 3-alkenyl-2-thioxoquinazoline-4-ones 6 and 7.
R
O
R
O
COOH
N
R
R
COOC2H5
(Et)3N
NCS
+
NCS
N
S
1.
N
H
6, 7
N
NH2
NH2
N
S
N
N
H
2. KOH
R= H(6), CH3 (7)
N
3. AcOH
R= H, CH3
1,2
Electrophilic
thioxoquinazoline-4-ones
methoxy(ethoxy)phenyltellurium trichloride was carry out
under the same conditions. As result, 2-(p-
alkoxyphenyl)dichlorotelluromethyl-2,3-dihydro-5H-[1,3]
thiazolo[2,3-b]quinazolin-5-ones 8–11 were synthesized.
The composition of compounds was proved by NMR
spectra and elemental analysis. It is found that the
refusing of electronic density of condensed benzene ring
does not effect on regiochemistry of heterocyclyzation
process; however, the yields of cyclized products are
significantly reduced. The influence of alkyl substituent
in electrophilic reagent is not significant (Scheme 4).
cyclization
of
7
3-alkenyl-2-
with the p-
dihydropyrazolo[3,4-d][1,3]thiazolo[3,2-a]pyrimidin-4(1H)-
ones 3 and 4 (Scheme 2). Obviously, the addition of
aryltellurium trichloride to exocyclic bond C═C is before
the heterocyclization process; moreover, the electrophile
acts on the terminal carbon of alkenyl fragment. The next
intramolecular cyclization is occured on the sulfur atom
with the annelation of the thiazolidine cycle. The structure
and composition of obtained tellurium-containing
polycyclic heterocycles were confirmed by nuclear
magnetic resonance (NMR) spectra, chromatography-mass
spectrometry, and elemental analysis. Results of spectral
investigation well agree with the data of halogenation for
similar objects [14]. Thus, type of condensed heterocycle
on alkenylthioxopirimidinone does not effect on
regiochemistry of process and yields of cyclized products.
The chemical properties of synthesized tellurium-
containing polycondensed heterocyclic compounds were
studied. The action of triple excess of sodium sulfite on
the solution of compound 4 in dimethyl sulfoxide
(DMSO) leads to dehydrochlorination of salt 4 and
dehalogenation of Tellurium atom, what were confirmed
by elemental analysis for compound 5 (Scheme 2). It is
important that the reduction by Na2SO3 does not split the
bond tellurium–carbon as described for the action of
sodium borohydride [11].
6
and
a
CONCLUSION
Thus, a changing of electronic density of condensed
cycle in 3-alkenyl-2-thioxopyrimidin-4-one does not
effect on regiochemistry of electrophilic intramolecular
cyclization process under the action of aryltellurium
trichlorides and leads to the formation of linear
annulation of thiazolidine cycle to condensed pyrimidine.
EXPERIMENTAL
For investigation of influence of condensed cycle in
pyrimidine moiety in reactions of electrophilic
cyclization, pirazol cycle was changed on benzene cycle,
which electronic density is less. The 3-alkenyl-2-
thioxoquinazoline-4-ones 6 and 7 were synthesized from
anthranilic acid for these purposes (Scheme 3).
The spectra of 1H NMR (400 MHz) and 13C NMR
(100 MHz) were recorded on Varian Mercury-400
instruments (Enamine Ltd, Kiyv, Ukraine). The chemical
shift values (δ) are given in parts per million (ppm)
downfield from TMS as internal standard and are referred
Scheme 2. Electrophilic heterocyclization of 5-alkenyl-6-thioxo-1-methylpyrazolo[3,4-d]pyrimidine-4-ones by p-methoxyphenyltellurium trichloride.
R
.
O
O
TeCl3
HCl
R
Cl
Te
N
N
AcOH
+
S
S
N
N
Cl
O
N
N
H
N
N
OCH3
3, 4
1, 2
3 equv Na2SO3
R= CH3
DMSO
O
N
Te
S
N
O
N
N
5
R= H(1, 3), CH3 (2, 4)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Regiochemistry of Electrophilic Heterocyclization of 3-Alkenyl-2-
Thioxopyrimidin-4-One by p-Alkoxyphenyltellurium Trichloride
Scheme 4. Electrophilic heterocyclization of 3-alkenyl-2-thioxoquinazoline-4-ones by p-methoxyphenyltellurium trichloride.
R
.
O
O
TeCl3
HCl
R
Cl
Te
N
N
AcOH
+
S
S
Cl
R1
N
N
H
OR1
8-11
6, 7
R= H (6, 8, 10), CH3 (7, 9, 11)
R1= CH3 (8, 9), C2H5 (10, 11)
to the residual peak of the deuterated solvent used
(CD3)2SO. Mass spectra were recorded on an Agilent
1100 LCMSD SL instrument (chemical ionization;
atmospheric pressure chemical ionization) and an Agilent
5890 Series II 5972 GCMS instrument (electron impact)
(Enamine Ltd, Kiyv, Ukraine). The melting points were
determined on Stuart SMP30 instrument (UK). Elemental
analyses were performed on Elementar Vario MICRO
cube analyzer (Elementar-Straße 1, Langenselbold,
Germany). All reagents were obtained from commercial
suppliers and used without any further purification.
Methallyl isothiocyanate was synthesized from Fizer [15].
Dry solvents were prepared according to the standard
methods. The p-methoxyphenyltellurium trihalides were
received according to described procedure [16].
1 or 2, dissolved in 20 mL of acetic acid, was added to
1 mmol of p-methoxyphenyltellutium trichloride in 20 mL
of acetic acid. The reaction mixture was stirring at room
temperature for 8 h. Target product was filtered and
recrystallized from acetic acid.
7-[Dichloro(4-methoxyphenyl)telluromethyl]-1-methyl-6,7-
dihydropyrazolo[3,4-d][1,3]thiazolo[3,2-a]pyrimidin-4(1H)-one
hydrochloride (3). Yield 70%; white powder (acetic acid);
mp. 156–158°C. 1H NMR (400 MHz, DMSO-d6): δ
(ppm) 8.46 (s, 1H), 8.05 (d, J = 8.5 Hz, 2H), 7.10 (d,
J = 7.7 Hz, 2H), 4.63 (m, 1H), 4.54 (d, J = 12.4 Hz, 1H),
4.35 (dd, J = 8.0, 5.8 Hz, 1H), 4.02 (t, J = 8 Hz, 1H),
3.95 (s, 3H), 3.89 (dd, J = 5.8, 5.2 Hz, 1H), 3.82 (s, 3H).
Mass (m/z): 221; 471; 475; 477. Anal. Calcd for
C16H17Cl3N4O2STe: С, 34.11; Н, 3.04; N, 9.95; S, 5.69.
Found: С, 35.78; Н, 3.12; N, 10.36; S, 5.92.
General procedure for the preparation of 5-alkenyl-6-thioxo-
1-methylpyrazolo[3,4-d]pyrimidine-4-ones. The 0.05 mol
7-[Dichloro(4-methoxyphenyl)telluromethyl]-1,7-dimethyl-6,7-
dihydropyrazolo[3,4-d][1,3]thiazolo[3,2-a]pyrimidin-4(1H)-one
of 5-amino-4-carbethoxy-1-methylpyrazole [17] was
dissolved in 30 mL of ethanol. The 0.05 mol of
alkenylisothiocianate was added to pre-prepared solution
of 5-amino-4-carbethoxy-1-methylpyrazole. The mixture
was refluxed for 8 h. Then, 0.1 mol of potassium
hydroxide in 5 mL of water was added. Reaction mixture
was refluxed for 2 h and cooled, and the yielded solution
was precipitated by acetic acid. Product was filtered,
hydrochloride (4).
Yield 75%; white powder (acetic
acid); mp. 187–188°C. 1H NMR (400 MHz,
DMSO-d6): (ppm) 8.46 (s, 1H), 8.04 (d,
δ
J = 8.8 Hz, 2H), 7.11 (d, J = 8.8 Hz, 2H), 4.80 (d,
J = 12.6 Hz, 1H), 4.35 (d, J = 12.6 Hz, 1H), 4.29
(d, J = 11.8 Hz, 1H), 4.19 (d, J = 11.8 Hz, 1H),
3.95 (s, 3H), 3.81 (s, 3H), 1.90 (s, 3H). 13С NMR:
δ (ppm) 161.7, 160.6, 159.3, 157.1, 135.8, 130.3, 125.6,
115.4, 104.6, 58.8, 58.1, 56.0, 53.6, 39.6, 28.8. Anal.
Calcd for C17H19Cl3N4O2STe: С, 35.36; Н, 3.32; N, 9.70;
S, 5.55. Found: С, 37.13; Н, 3.37; N, 10.15; S, 5.73.
washed by water, and recrystallized from ethanol.
1-Methyl-5-(prop-2-en-1-yl)-1,5,6,7-tetrahydro-4H-pyrazolo
[3,4-d]pyrimidin-4-one (1).
Yield 61%; white powder
(ethanol); mp. 214–215°C; 1H NMR (400 MHz,
DMSO-d6): δ (ppm) 13.31 (s, 1H), 8.47 (s, 1H), 5.87
(m, 1H), 5.10 (d, J = 8.0 Hz, 1H), 5.07 (d, J = 14.0 Hz,
1H), 4.99 (d, J = 5.0 Hz, 2H), 3.90 (s, 3H). Anal. Calcd
for C9H10N4OS: С, 48.64; Н, 4.53; N, 25.21; S, 14.42.
Preparation of 7-[(4-methoxyphenyl)telluromethyl]-1,7-dimethyl-
6,7-dihydropyrazolo[3,4-d][1,3]thiazolo[3,2-a]pyrimidin-4(1H)-
one (5).
To 3 mmol of hydrochloride 4, dissolved in
20 mL of DMSO, 9 mmol of water solution of sodium
sulfite was dropped. Mixture was stirring at room
temperature for 2 h. Target product was filtered and
washed by water. Yield 71%; white powder (acetic acid);
mp. 165–167°C. 1H NMR (400 MHz, DMSO-d6): δ (ppm)
8.44 (s, 1H), 7.69 (d, J = 8.2 Hz, 2H), 6.82 (d, J = 8.1 Hz,
2H), 4.33 (d, J = 12.2 Hz, 1H), 4.20 (d, J = 12.6 Hz, 1H),
3.95 (s, 3H), 3.74 (s, 3H), 3.48 (s, 2H), 1.60 (s, 3H). Anal.
Calcd for C17H18N4O2STe: C, 43.44; H, 3.86, N. 11.92; S,
6.82. Found: C, 43.34; H, 3.81; N, 11.61; S, 7.03.
Found: С, 48.51; Н, 4.45; N, 25.03; S, 14.28.
1-Methyl-5-(2-methylprop-2-en-1-yl)-1,5,6,7-tetrahydro-4H-
pyrazolo[3,4-d]pyrimidin-4-one (2). Yield 61%; white powder
(ethanol); mp. 207–208°C. 1H NMR (400 MHz, DMSO-d6):
δ (ppm) 13.31 (s, 1H), 8.47 (s, 1H), 4.87 (s, 2H), 4.73 (s, 1H),
4.43 (s, 1H), 3.90 (s, 3H), 1.72 (s, 3H). Anal. Calcd for
C10H12N4OS: С, 50.83; Н, 5.12; N, 23.71; S, 13.57.
Found: С, 50.64; Н, 4.96; N, 23.52; S, 13.43.
General procedure for the preparation of 7-(p-methoxyphenil)
dichloromethyl-1,4,6,7-tetrahydropyrazolo[3,4-d][1,3]-thiazolo
[3,2-a]pyrimidine-4-ones hydrochlorides. The 1 mmol of
General procedure for the preparation of 3-alkenyl-2,3-
dihydroquinazoline-4(1H)-ones.
The 0.05 mol alkenyl
5-alkenyl-6-thioxo-1-methylpyrazolo[3,4-d]pyrimidine-4-one
isothiocyanate was added to 0.05 mol of anthranilic acid
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

M. Kut, M. Onysko, and V. Lendel
Vol 000
in 20 mL of triethylamine. The reaction mixture was
refluxed for 2 h. Precipitate was filtered and washed by
J = 7.2 Hz, 2H), 7.78 (t, J = 7.6 Hz, 1H), 7.55 (d,
J = 8.0 Hz, 1H), 7.46 (t, J = 8 Hz, 1H), 7.55 (d,
J = 8.4 Hz, 1H), 7.08 (d, J = 7.2 Hz, 1H), 4.76 (m,
1H), 4.67 (d, J = 12.8 Hz, 1H), 4.44 (dd, J = 12.8,
7.2 Hz, 1H), 4.09 (m, 3H), 3.94 (dd, J = 12.0, 6 Hz,
2H), 1.33 (t, J = 6.4 Hz 3H). 13С NMR δ (ppm)
160.98, 160.10, 159.77, 147.80, 135.89, 135.73, 126.57,
125.24, 123.10, 119.42, 115.75, 63.94, 54.37, 49.86, 41.38,
14.97. Anal. Calcd for C19H19Cl3N2O2STe: С, 39.80; Н, 3.34;
methanol. The product was crystalized from ethanol.
3-Prop-2-en-1-yl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one
(6). Yield 61%; white powder (ethanol); mp. 203–205°C;
1
mp. 201°C [18]; IR (KBr): (v/смÀ1) = 1648 (C═O); H
NMR (400 MHz, DMSO-d6): δ (ppm) 12.94 (s, 1H),
7.92 (d, J = 8.0 Hz, 1H), 7.72 (t, J = 7.8 Hz, 1H), 7.39
(d, J = 8.4 Hz, 1H), 7.31 (t, J = 7.6 Hz, 1H), 5.90 (m,
1H), 5.15 (dd, J = 5.2, 1.2 Hz, 1H), 5.12 (d, J = 1.6, Hz
1H), 5.03 (d, J = 3.6 Hz, 2H). 13С NMR: δ (ppm)
175.51, 159.43, 139.54, 135.91, 132.24, 127.72, 124.92,
117.58, 116.08, 115.86, 48.07. Anal. Calcd for
C11H10N2OS: С, 60.53; Н, 4.62; N, 12.83; S, 14.69.
N, 4.89; S, 5.59. Found: С, 41.82; Н, 3.44; N, 5.07; S, 5.80.
3-[Dichloro(4-methoxyphenyl)telluromethyl]-3-methyl-2,3-
dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one hydrochloride
(9). Yield 56%; white powder (acetic acid); mp. 177–
178°C. IR (KBr): (v/смÀ1) = 1692 (С═О); 1H NMR
(400 MHz, DMSO-d6) δ (ppm) 8.09 (d, J = 8.0 Hz, 1H),
8.06 (d, J = 7.2 Hz, 2H), 7.77 (t, J = 6.8 Hz, 1H), 7.54
(d, J = 8.4 Hz, 1H), 7.44 (t, J = 7.2 Hz, 1H), 7.10
(d, J = 7.2 Hz, 2H), 4.94 (d, J = 12.4 Hz, 1H), 4.45 (d,
J = 12.8, 1H), 4.33 (d, J = 11.8, 1H), 4.24 (d,
J = 11.8 Hz, 1H), 3.80 (s, 3H), 1.93 (s, 3H). 13С NMR δ
(ppm) 161.69, 160.79, 159.87, 148.58, 136.01, 135.75,
126.80, 126.10, 125.62, 119.65, 115.33, 59.44, 58.02,
56.03, 54.20, 28.89. Anal. Calcd for C19H19Cl3N2O2STe:
С, 39.80; Н, 3.34; N, 4.89; S, 5.59. Found: С, 41.83; Н,
Found: С, 60.43; Н, 4.55; N, 12.70; S, 14.60.
3-(2-Methylprop-2-en-1-yl)-2-thioxo-2,3-dihydroquinazolin-
4(1H)-one (7). Yield 61%; white powder (ethanol); mp.
1
212–214°C. IR (KBr): (v/смÀ1) = 1655 (С═О); H NMR
(400 MHz, DMSO-d6) δ (ppm) 12.93 (s, 1H), 7.95 (d,
J = 7.2 Hz, 1H), 7.75 (t, J = 7.6 Hz, 1H), 7.37 (d,
J = 8.4 Hz, 1H), 7.34 (t, J = 7.6 Hz, 1H), 4.92 (s, 2H),
4.72 (s, 1H), 4.46 (s, 1H), 1.73 (s, 3H). 13С NMR: δ
(ppm) 175.82, 159.41, 139.53, 139.26, 135.83, 127.75,
124.81, 116.07, 115.70, 109.40, 50.54, 20.88. Anal.
Calcd for C12H12N2OS: С, 62.05; Н, 5.21; N, 12.06; S,
13.80. Found: С, 61.95; Н, 5.12; N, 11.93; S, 13.74.
3.45; N, 5.08; S, 5.78.
3-[Dichloro(4-ethoxyphenyl)telluromethyl]-3-methyl-2,3-
dihydro-5H-[1,3]thiazolo[2,3-b]quinazolin-5-one hydrochloride
General procedure for the preparation of 7-(p-
methoxyphenyl)dichlorotelluromethyl-2,3-dihydro-5H-[1,3]
thiazolo[2,3-b]quinazolin-5-ones hydrochlorides. The 1 mmol
of 3-alkenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one 6 or
7, dissolved in 20 mL of acetic acid, was added to 1 mmol
of p-alkoxyphenyltellutium trichloride in 20 mL of acetic
acid. The reaction mixture was stirring at room temperature
for 8 h. Target product was filtered and recrystallized from
(11).
Yield 53%; white powder (acetic acid); mp.
176–178°C. IR (KBr): (v/смÀ1) = 1694 (С═О); H NMR
(400 MHz, DMSO-d6) δ (ppm) 8.08 (d, J = 8.0 Hz,
1H), 8.05 (d, J = 7.2 Hz, 2H),7.76 (t, J = 6.8 Hz, 1H),
7.54 (d, J = 8.4 Hz, 1H), 7.45 (t, J = 7.2 Hz, 1H),
7.10 (d, J = 7.2 Hz, 2H), 4.93 (d, J = 13.2 Hz,
1H), 4.45 (d, J = 12.4, 1H), 4.32 (d, J = 11.6, 1H),
4.24 (d, J = 11.2 Hz, 1H), 4.08 (m, 3H), 1.92 (s, 3H),
1.33 (t, J = 6.4 Hz, 3H). 13С NMR δ (ppm) 160.98,
160.07, 159.88, 148.68, 135.78, 135.08, 126.64,
126.17, 125.29, 119.71, 115.72, 63.96, 58.07, 56.31,
1
acetic acid.
3-[Dichloro(4-methoxyphenyl)telluromethyl]-2,3-dihydro-5H-
[1,3]thiazolo[2,3-b]quinazolin-5-one hydrochloride (8). Yield
55%; white powder (acetic acid); mp. 143–145°C; IR
(KBr): (v/смÀ1) = 1690 (С═О); 1H NMR (400 MHz,
DMSO-d6) δ (ppm) 8.07 (d, J = 8.0 Hz, 1H), 8.05
(d, J = 7.2 Hz, 2H), 7.78 (t, J = 7.6 Hz, 1H), 7.55 (d,
J = 8.4 Hz, 1H), 7.46 (t, J = 8 Hz, 1H), 7.55 (d,
J = 8.4 Hz, 1H), 7.08 (d, J = 7.2 Hz, 1H), 4.76 (m, 1H),
4.67 (d, J = 13.2 Hz, 1H), 4.44 (dd, J = 12.8, 7.2 Hz, 1H),
4.10 (t, J = 10.4, Hz, 1H), 3.94 (dd, J = 12.4, 5.6 Hz, 2H),
3.81 (s, 3H). 13С NMR δ (ppm) 161.66, 160.35, 159.69,
147.44, 135.89, 135.25, 126.62, 125.79, 125.03, 123.10,
119.38, 115.36, 55.97, 54.41, 49.83, 41.52. Anal. Calcd
for C18H17Cl3N2O2STe: С, 38.65; Н, 3.06; N, 5.01; S,
53.99,
28.89,
14.97.
Anal.
Calcd
for
C20H21Cl3N2O2STe: С, 40.89; Н, 3.60; N, 4.77; S,
5.46. Found: С, 42.85; Н, 3.70; N, 4.96; S, 5.68.
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Heterocycl Cоmmun 2013, 19, 189.
5.73. Found: С, 40.63; Н, 3.15; N, 5.24; S, 5.91.
3-[Dichloro(4-ethoxyphenyl)telluromethyl]-2,3-dihydro-5H-
[1,3]thiazolo[2,3-b]quinazolin-5-one hydrochloride (10). Yield
52%; white powder (acetic acid); mp. 148–149°C. IR
(KBr): (v/смÀ1) = 1691 (С═О); 1H NMR (400 MHz,
DMSO-d6) δ (ppm) 8.08 (d, J = 8.0 Hz, 1H), 8.04 (d,
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Regiochemistry of Electrophilic Heterocyclization of 3-Alkenyl-2-
Thioxopyrimidin-4-One by p-Alkoxyphenyltellurium Trichloride
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DOI 10.1002/jhet