Heterocyclization of 5,6-disubstituted 3-alkenyl-2-thioxothieno[2,3-d]pyrimidin-4-one with p-alkoxyphenyltellurium trichloride

Article abstract of DOI:10.1515/hc-2016-0169

Electrophilic heterocyclization of 5,6-disubstituted 3-alkenyl-2-thioxothieno[2,3-d]pyrimidin-4-ones by treatment with p-alkoxyphenyltellurium trichlorides leads to annulation of the thiazoline moiety with the formation of 6,7-disubstituted-2-[dichloro-(p-alkoxyphenyl)telluromethyl]-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin-5-one hydrochlorides.

Full text of DOI:10.1515/hc-2016-0169

Heterocycl. Commun. 2016; 22(6): 347–350
MHyekotlaeKruot, cMiykhcaljliozOanytsikoo*nandoVfas5yl,L6en-ddelisubstituted
3-alkenyl-2-thioxothieno[2,3-d]pyrimidin-4-one
with p-alkoxyphenyltellurium trichloride
DOI 10.1515/hc-2016-0169
Received October 5, 2016; accepted October 31, 2016; previously
published online November 28, 2016
Results and discussion
5,6-Disubstituted-2-thioxothieno[2,3-d]pyrimidin-4-ones
Abstract: Electrophilic heterocyclization of 5,6-disubsti- 1–6 were synthesized as shown in Scheme 1 and used
tuted
3-alkenyl-2-thioxothieno[2,3-d]pyrimidin-4-ones subsequently as substrates for electrophilic heterocycli-
by treatment with p-alkoxyphenyltellurium trichlorides zation in the presence of p-alkoxyphenyltellurium trihal-
leads to annulation of the thiazoline moiety with the ides (Scheme 2). The model compounds 1–6 contain a few
formation of 6,7-disubstituted-2-[dichloro-(p-alkoxyphe- nucleophilic centers in the molecule, which provides an
nyl)telluromethyl]-2,3-dihydro-5Н-[1,3]thiazolo[3,2-а] opportunity to study regioselectivity of the electrophilic
thieno[2,3-d]pyrimidin-5-one hydrochlorides.
cyclization. Although several cyclization pathways could
be suggested (not shown), the reaction takes a single route
indicated in Scheme 2.
The heterocyclization was successfully conducted in
acetic acid, chloroform and acetonitrile at different tem-
peratures. It was found that under the optimal conditions
the electrophilic heterocyclization is conducted in acetic
acid at room temperature. The tellurium-containing com-
pounds 7–15 were regioselectively obtained as the only
Keywords:
3-alkenyl-2-thioxothieno[2,3-d]pyrimidine-
4-one; [1,3]thiazolo[3,2-а]thieno[2,3-d]pyrimidin-5-one;
electrophilic cyclization; p-alkoxyphenyltellurium trichlo-
ride; regioselectivity.
Introduction
Organotellurium compounds show anti-cancer [1–3], anti- products. It can be suggested that the addition of aryl-
oxidant [3, 4] and anti-bacterial activity [5] and are used in tellurium trichloride to a double bond of 1–6 takes place
neuropathy [6–11]. In this study we analyzed a new route to generate the intermediate product A which is a direct
of introduction of tellurium into a heterocyclic system. precursor to the final product 7–15. In one case the hydro-
Electrophilic heterocyclization of unsaturated substrates chloride 14 was transformed into a free base 16 (Scheme 2)
under the action of tellurium tetrahalides is described by treatment with sodium sulfite. This is a remarkable
for obtaining tellurium-containing fused heterocyclic result because the expected reduction of tellurium was
systems [12–14]. Using for the same purpose aryltellurium not observed. All products 1–16 were fully characterized
trihalides is barely mentioned in the literature. Indeed, by spectral methods and elemental analysis.
there are only few data about using aryltellurium trihal-
ides in the reaction with unsaturated alcohols, phenols
and acids [15–18]. We choose the N-alkenyl derivatives of
5,6-disubstituted-2-thioxothieno[2,3-d]pyrimidin-4-one Conclusion
as the objects for study electrofilic heterocyclization by
p-alkoxyphenyltellurium trihalides.
Electrofilic heterocyclization of N-alkenyl-substituted
2-thioxotieno[2,3-d]pyrimidin-4-ones 1–6 in the presence
of an aryltellurium trichloride was investigated. The reac-
tion is highly regioselective.
*Corresponding author: Mikhajlo Onysko, Organic Synthesis
Laboratory, Uzhhorod National University, Uzhhorod 88000,
Ukraine, e-mail: muonysko@gmail.com
Mykola Kut and Vasyl Lendel: Organic Synthesis Laboratory,
Uzhhorod National University, Uzhhorod 88000, Ukraine
Experimental
1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were recorded
in DMSO-d6 on a Varian Mercury-400 instrument. Melting points
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348ꢀ ꢀM. Kut et al.: p-Alkoxyphenyltellurium trichloride
1: R = H; R1 = R2 = Me
2: R = R1 = R2 = Me
O
R
R
O
R1
R2
OEt
HN
R1
R2
COOEt
NH2
R1
R2
R
NCS
N
3: R = H; R1R2 = (CH2)4
4: R = Me; R1R2 = (CH2)4
5: R = H; R1R2 = (CH2)3
6: R = Me; R1R2 = (CH2)3
1. KOH
S
2. AcOH
N
N
H
S
S
S
S
H
1–6
Scheme 1ꢁSynthesis of 5,6-disubstituted 2-thioxothieno[2,3-d]pyrimidin-4-ones 1–6.
TeCl3
OR3
O
OR3
R
R1
R2
R1
S
O
N
N
AcOH
Cl
Te
Cl
R
7: R = H; R1 = R2 = Me; R3 = Me
8: R = Me; R1 = R2 = Me; R3 = Me
9: R = H; R1 = R2 = Me; R3 = Et
10: R = Me; R1 = R2 = Me; R3 = Et
11: R = H; R1R2 = (CH2)4; R3 = Me
12: R = Me; R1R2 = (CH2)4; R3 = Me
13: R = H; R1R2 = (CH2)4; R3 = Et
14: R = Me; R1R2 = (CH2)4; R3 = Et
15: R = Me; R1R2 = (CH2)3; R3 = Me
N
S
R2
N
Cl
SH
S
H
A
1–6
O
N
R1
O
N
OR3
OEt
Me
Na2SO3
R
Cl
Te
Cl
Cl
Te
Cl
N
N
R2
S
S
S
S
HCl
7–15
16
Scheme 2ꢁSynthesis of 6,7-disubstituted-2-(dichloro(p-alkoxyphenyl)telluromethyl)-2,3-dihydro-5Н-[1,3]thiazolo[3,2-а]thieno[2,3-d]
pyrimidin-5-ones hydrochlorides.
were determined on a Stuart SMP30 instrument. Elemental analyses 3-(2-Methylprop-2-en-1-yl)-2-thioxo-2,3,5,6,7,8-hexahydro[1]
were performed on an Elementar Vario analyzer. All reagents were benzothieno[2,3-d]pyrimidin-4(1H)-one (4)ꢀYield 85%.; mp 202–
1
obtained from commercial suppliers and used without further purifi- 204°С; H NMR: δ 13.56 (s, 1H), 4.85 (s, 2H), 4.72 (s, 1H), 4.42 (s, 1H),
cation. Anhydrous solvents were prepared according to the standard 2.75 (m, 2H), 2.64 (m, 2H), 1.77 (m, 4H), 1.72 (s, 3H); 13C NMR: δ 174.3,
methods. The p-alkoxyphenyltellurium trihalides were synthesized 156.7, 149.4, 139.4, 131.5, 129.1, 116.0, 109.3, 50.3, 25.4, 24.5, 23.0, 22.1,
according to the literature procedure [19].
21.1. Anal. Calcd for C14H16N2OS2: C, 57.50; H, 5.52; N. 9.58. Found: C,
57.11; H, 5.39; N, 9.41.
3-(Prop-2-en-1-yl)-2-thioxo-1,2,3,5,6,7-hexahydro-4H-cyclo-
penta[4,5]thieno[2,3-d]pyrimidin-4-one (5)ꢀYield 85%; mp
Synthesis of 5,6-disubstituted 3-alkenyl-
2-thioxothieno[2,3-d]pyrimidin-4-ones 1–6
1
223–224°С; H NMR: δ 13.61 (s, 1H), 5.88 (m, 1H), 5.14 (s, 1H), 5.10 (d,
Jꢁ=ꢁ6.5 Hz 1H), 4.96 (d, Jꢁ=ꢁ5.1 Hz, 2H), 2.82 (t, Jꢁ=ꢁ7.2 Hz, 4H), 2.41–2.29
(m, 2H). Anal. Calcd for C12H12N2OS2: C, 54.52; H, 4.85; N. 10.60. Found:
C, 53.98; H, 4.69; N, 10.48.
A solution of an ethyl 2-aminothiophene-3-carboxylate (0.05 mol) and
allyl or methallyl isothiocyanate [20] (0.05 mol) in ethanol (40 mL)
was heated under reflux for 8 h and then treated with an aqueous
solution (5 mL) of potassium hydroxide (0.1 mol). The mixture was
heated for an additional 2 h, cooled and diluted with aqueous acetic
acid. The resultant precipitate of 1–6 was crystallized from ethanol.
3-(2-Methyl-prop-2-en-1-yl)-2-thioxo-1,2,3,5,6,7-hexahydro-
4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one (6)ꢀYield 85%;
mp 209–210°С; 1H NMR: δ 13.47 (s, 1H), 4.89 (s, 2H), 4.74 (s, 1H), 4.47
(s, 1H), 2.82 (t, J 6.7 Hz, 4H), 2.41–2.27 (m, 2H), 1.73 (s, 3H); 13C NMR: δ
174.3, 156.4, 153.8, 140.5, 139.3, 134.2, 113.2, 109.3, 50.3, 29.0, 28.7, 28.2,
21.0. Anal. Calcd for C13H14N2OS2: C, 56.09; H, 5.07; N. 10.06. Found: C,
56.11; H, 5.12; N, 10.11.
5,6-Dimethyl-3-(prop-2-en-1-yl)-2-thioxo-2,3-dihydrothieno[2,3-
d]pyrimidin-4(1H)-one (1)ꢀYield 89%.; mp 211–212°С; lit. mp 191–
192°С [21] and 209–212°С [22].
5 ,6 - D i m e t hyl-3- ( 2- m e t hyl p r o p -2- e n -1-yl ) -2- t h i oxo -
2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one (2)ꢀYield 89%; mp
Synthesis of 6,7-disubstituted-2-(dichloro(p-alkoxyphenyl)-
telluromethyl)-2,3-dihydro-5Н-[1,3]thiazolo[3,2-а]
thieno[2,3-d]pyrimidin-5-ones hydrochlorides 7–15
1
189–190°С; H NMR: δ 13.53 (s, 1H), 4.85 (s, 2H), 4.71 (s, 1H), 4.42 (s,
1H), 2.25 (s, 6H), 1.72 (s, 3H); 13C NMR: δ 174.1, 156.8, 148.6, 139.3, 129.3,
125.8, 116.6, 109.2, 50.3, 21.0, 13.0, 12.5. Anal. Calcd for C12H14N2OS2: C,
54.11; H, 5.30; N. 10.52. Found: C, 53.87; H, 5.28; N, 10.44.
A mixture of 5,6-disubstituted 2-thioxothieno[2,3-d]pyrimidin-4-one
3-(Prop-2-en-1-yl)-2-thioxo-2,3,5,6,7,8-hexahydro[1]ben- 1–6 (1 mmol) and p-alkoxyphenyltellurium trichloride (1 mmol)
zothieno[2,3-d]pyrimidin-4(1H)-one (3)ꢀYield 85%.; mp 218–219°С; in acetic acid (40 mL) was stirred at room temperature for 8 h. The
lit. mp 205–208°С [22].
resultant precipitate was filtered and crystallized from acetic acid.
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M. Kut et al.: p-Alkoxyphenyltellurium trichlorideꢀ
ꢀ349
6,7-Dimethyl-2-[dichloro(4-methoxyphenyl)tellurylmethyl]- 2-(Dichloro(4-ethoxyphenyl)tellurylmethyl)-2,3,6,7,8,9-hexahydro-
2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin- 5H-benzo[4,5]thieno[2,3-d][1,3]thiazolo[3,2-a]pyrimidin-5-one
1
5-one hydrochloride (7)ꢀYield 73%; mp 201–202°С; 1H NMR: δ 8.05 hydrochloride (13)ꢀYield 73%; mp 216–218°С; H NMR: δ 8.04 (d,
(d, Jꢁ=ꢁ8.9 Hz, 2H), 7.09 (d, Jꢁ=ꢁ8.9 Hz, 2H), 4.69 (m, 1H), 4.60 (dd, Jꢁ=ꢁ13.0 Jꢁ=ꢁ8.3 Hz, 2H), 7.08 (d, Jꢁ=ꢁ8.3 Hz, 2H), 4.71 (m, 1H), 4.58 (d, Jꢁ=ꢁ13.0 Hz, 1H),
and 2.6 Hz, 1H), 4.38 (dd, Jꢁ=ꢁ12.9 and 7.2 Hz, 1H), 4.04 (dd, Jꢁ=ꢁ11.8 and 4.40 (dd, Jꢁ=ꢁ12.0 and 7.7 Hz, 1H), 4.16–3.98 (m, 3H), 3.92 (dd, Jꢁ=ꢁ10.5 and
8.7 Hz, 1H), 3.91 (dd, Jꢁ=ꢁ13.0 and 2.6 Hz, 1 H), 3.82 (s, 3H), 2.32 (s, 6H); 5.9 Hz, 1H), 2.83 (m, 2H), 2.70 (m, 2H), 1.77 (m, 4H), 1.35 (t, Jꢁ=ꢁ6.6 Hz, 3H);
13C NMR: δ 162.2, 158.8, 157.1, 135.9, 128.8, 128.7, 125.6, 119.7, 115.4, 56.0, 13C NMR: δ 163.0, 161.0, 159.0, 156.9, 131.4, 130.9, 125.4, 118.9, 115.8, 64.0,
54.1, 49.9, 13.2. Anal. Calcd for C18H19Cl3N2O2S2Te: C, 36.31; H, 3.55; Cl, 54.1, 49.8, 25.7, 24.9, 23.0, 22.2, 15.0. Anal. Calcd for C21H23Cl3N2O2S2Te: C,
17.86; N. 4.70. Found: C, 36.11; H, 3.39; Cl, 17.52; N, 4.58.
39.69; H, 3.96; Cl, 16.74; N. 4.41. Found: C, 39.33; H, 3.77; Cl, 16.57; N, 4.29.
2,6,7-Trimethyl-2-(dichloro(4-methoxyphenyl)tellurylmethyl)- 2-Methyl-2-(dichloro(4-ethoxyphenyl)tellurylmethyl)-
2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin- 2,3,6,7,8,9-hexahydro-5H-benzo[4,5]thieno[2,3-d][1,3]
5-one hydrochloride (8)ꢀYield 73%; mp 206–207°С; 1H NMR: δ 8.05 thiazolo[3,2-a]pyrimidin-5-one hydrochloride (14)ꢀYield 73%;
(d, Jꢁ=ꢁ8.9 Hz, 2H), 7.11 (d, Jꢁ=ꢁ9.0 Hz, 2H), 4.85 (d, Jꢁ=ꢁ12.9 Hz, 1H), 4.41 mp 208–209°С; 1H NMR: δ 8.05 (d, Jꢁ=ꢁ7.4 Hz, 2H), 7.10 (d, Jꢁ=ꢁ7.8 Hz, 2H),
(d, J 12.9 Hz, 1H), 4.31 (d, Jꢁ=ꢁ11.9 Hz, 1H), 4.22(d, J 11.9 Hz, 1H), 3.81 (s, 4.86 (d, Jꢁ=ꢁ12.9 Hz, 1H), 4.41 (d, Jꢁ=ꢁ13.0 Hz, 1H), 4.32 (d, Jꢁ=ꢁ11.5 Hz, 1H),
3H), 2.34 (s, 6H), 1.91 (s, 3H); 13C NMR: δ 162.0, 161.7, 158.6, 157.1, 135.8, 4.24 (d, Jꢁ=ꢁ11.6 Hz, 1H), 4.12 (q, Jꢁ=ꢁ7.0 Hz, 2H), 2.85(m, 2H), 2.72 (m,
129.0, 128.7, 125.6, 119.9, 115.4, 59.3, 57.8, 56.0, 54.6, 29.0, 13.2. Anal. 2H), 1.93 (s, 3H), 1.78 (m, 4H), 1.35 (t, Jꢁ=ꢁ7.0 Hz, 3H); 13C NMR: δ 162.9,
Calcd for C19H21Cl3N2O2S2Te: C, 37.44; H, 3.80; Cl, 17.45; N. 4.60. Found: 161.1, 158.8, 156.9, 135.9, 115.8, 64.1, 59.3, 57.9, 54.8, 29.0, 25.8, 25.0, 23.1,
C, 37.19; H, 3.69; Cl, 17.28; N, 4.49.
22.3, 15.1. Anal. Calcd for C22H25Cl3N2O2S2Te: C, 40.68; H, 4.19; Cl, 16.37;
N. 4.31. Found: C, 40.11; H, 4.05; Cl, 16.15; N, 4.26.
6,7-Dimethyl-2-(dichloro(4-ethoxyphenyl)tellurylmethyl)-
2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin- 2-Methyl-2-(dichloro(4-methoxyphenyl)tellurylmethyl)-2,3,7,8-
5-one hydrochloride (9)ꢀYield 73%; mp 217–218°С; 1H NMR: δ tetrahydro-5H,6H-cyclopenta[4,5]thieno[2,3-d][1,3]thiazolo[3,2-
8.03 (d, Jꢁ=ꢁ8.8 Hz, 2H), 7.08 (d, Jꢁ=ꢁ8.8 Hz, 2H), 4.68 (m, 1H), 4.60 (d, a]pyrimidin-5-one hydrochloride (15)ꢀYield 70%; mp 180–181°С;
Jꢁ=ꢁ12.8 Hz, 1H), 4.38 (dd, Jꢁ=ꢁ12.8, 7.2 Hz, 1H), 4.09 (dt, Jꢁ=ꢁ10.5 and 1H NMR: δ 8.05 (d, Jꢁ=ꢁ8.9 Hz, 2H), 7.11 (d, Jꢁ=ꢁ8.9 Hz, 2H), 4.87 (d,
5.2 Hz, 2H), 4.02 (d, Jꢁ=ꢁ8.6 Hz, 1H), 3.90 (dd, Jꢁ=ꢁ11.8 and 5.9 Hz, 1H), Jꢁ=ꢁ12.9 Hz, 1H), 4.42 (d, Jꢁ=ꢁ12.9 Hz, 1H), 4.30 (d, Jꢁ=ꢁ11.9, Hz, 1H), 4.22
2.33 (s, 6H), 1.34 (t, Jꢁ=ꢁ6.9 Hz, 3H); 13C NMR: δ 162.2, 161.0, 158.9, 157.2, (d, Jꢁ=ꢁ11.9 Hz, 1H), 3.81(s, 3H), 2.88 (t, Jꢁ=ꢁ6.9 Hz, 4H), 2.41–2.30 (m,
135.9, 128.8, 128.5, 125.3, 119.7, 115.8, 64.0, 54.1, 49.8, 15.0, 13.2. Anal. 2H), 1.91 (s, 3H); 13C NMR: δ 167.9, 158.4, 156.5, 139.7, 136.8, 135.8, 125.6,
Calcd for C19H21Cl3N2O2S2Te: C, 37.44; H, 3.80; Cl, 17.45; N. 4.60. Found: 116.7, 115.4, 59.2, 57.8, 56.0, 54.7, 29.5, 29.0, 28.8, 28.6, 27.9. Anal. Calcd
C, 37.26; H, 3.62; Cl, 17.36; N, 4.45.
for C21H23Cl3N2O2S2Te: C, 39.69; H, 3.96; Cl, 16.74; N. 4.41. Found: C,
39.48; H, 3.88; Cl, 16.64; N, 4.32.
2,6,7-Trimethyl-2-(dichloro(4-ethoxyphenyl)tellurylmethyl)-
2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin- Synthesis of 2-methyl-2-(dichloro(4-ethoxyphenyl)telluryl-
1
5-one hydrochloride (10)ꢀYield 73%; mp 201–202°С; H NMR: δ methyl)-2,3,6,7,8,9-hexahydro-5H-benzo[4,5]thieno[2,3-d][1,3]
8.03 (d, Jꢁ=ꢁ8.8 Hz, 2H), 7.10 (d, Jꢁ=ꢁ8.8 Hz, 2H), 4.85 (d, Jꢁ=ꢁ12.9 Hz, 1H), thiazolo[3,2-a]pyrimidin-5-one (16)ꢀA solution of hydrochloride
4.41 (d, Jꢁ=ꢁ12.9 Hz, 1H), 4.30 (d, Jꢁ=ꢁ11.9 Hz, 1H), 4.22 (d, Jꢁ=ꢁ11.6 Hz, 14 (0.3 mmol) in DMSO (10 mL) was treated dropwise with a solution
1H), 4.09 (q, Jꢁ=ꢁ7.0 Hz, 1H), 2.34 (s, 6H), 1.91 (s, 3H), 1.34 (t, Jꢁ=ꢁ7.0 Hz, of sodium sulfite (1.2 mmol) in water (5 mL). The resultant white pre-
3H); 13C NMR: δ 162.0, 161.0, 158.6, 157.1, 135.8, 129.0, 128.7, 125.3, cipitate was filtered, washed with water and crystallized from acetic
119.9, 115.7, 64.0, 59.3, 57.8, 54.6, 29.0, 15.0, 13.3, 13.1. Anal. Calcd for acid; yield 70%; mp 95–96°С; 1H NMR: δ 7,67 (d, Jꢁ=ꢁ8.5 Hz, 3H), 6,80
C20H23Cl3N2O2S2Te: C, 38.53; H, 4.04; Cl, 17.06; N. 4.49. Found: C, 38.35; (d, Jꢁ=ꢁ8.5 Hz, 3H), 4.38 (d, Jꢁ=ꢁ12.6 Hz, 2H), 4.00 (q, Jꢁ=ꢁ7 Hz, 3H), 3.49
H, 3.97; Cl, 16.96; N, 4.40.
(s, 3H), 3.32 (s, 9H), 2.80 (s, 4H), 2.69 (s, 4H), 2.54 (s, 2H), 1.80–1.66
(m, 8H), 1.62 (s, 5H), 1.31 (dd, Jꢁ=ꢁ14.8 and 7.8 Hz, 6H); 13C NMR: δ 159.3,
2-(Dichloro(4-methoxyphenyl)tellurylmethyl)-2,3,6,7,8,9-hexa- 157.0, 140.8, 131.4, 131.1, 116.5, 63.6, 59.1, 57.4, 28.1, 25.8, 25.0, 23.1, 22.3,
hydro-5H-benzo[4,5]thieno[2,3-d][1,3]thiazolo[3,2-a]pyrimidin- 22.5, 15.2. Anal. Calcd for C22H24Cl2N2O2S2Te: C, 43.10; H, 4.2;, Cl, 11.57;
5-one hydrochloride (11)ꢀYield 74%.; mp 213–214°С; 1H NMR: δ 8.05 N. 4.57. Found: C, 43.15; H, 4.39; Cl, 11.71; N, 4.61.
(d, Jꢁ=ꢁ8.9 Hz, 2H), 7.10 (d, Jꢁ=ꢁ8.9 Hz, 2H), 4.69 (m, 1H), 4.61 (dd, Jꢁ=ꢁ13.1
and 2.6 Hz, 1H), 4.39 (dd, Jꢁ=ꢁ12.9 and 7.1, Hz, 1H), 4.04 (dd, Jꢁ=ꢁ11.8 and
8.7 Hz, 1H), 3.91 (dd, Jꢁ=ꢁ11.8 and 6.0 Hz, 1H), 2.83 (m, 2H), 2.71 (m, 2H),
References
1.77 (m, 4H). Anal. Calcd for C20H21Cl3N2O2S2Te: C, 38.65; H, 3.73; Cl,
17.11; N. 4.51. Found: C, 38.11; H, 3.59; Cl, 17.02; N, 4.41.
[1] Cunha, R. L. O. R.; Urano, M. E.; Chagas, J. R.; Almeida, P. C.;
2-Methyl-2-(dichloro(4-methoxyphenyl)tellurylmethyl)-
2,3,6,7,8,9-hexahydro-5H-benzo[4,5]thieno[2,3-d][1,3]
thiazolo[3,2-a]pyrimidin-5-one hydrochloride (12)ꢀYield 74%;
Bincoletto, C.; Tersariolb, I. L. S.; Comasseto, J. V. Tellurium-
based cysteine protease inhibitors: evaluation of novel
organotellurium(IV) compounds as inhibitors of human cathep-
sin B. Bioorg. Med. Chem. Lett. 2005, 15, 755–760.
1
mp 228–230°С; H NMR: δ 8.07 (d, Jꢁ=ꢁ8.8 Hz, 2H), 7.13 (d, Jꢁ=ꢁ8.8 Hz,
2H), 4.86 (d, Jꢁ=ꢁ13.0 Hz, 1H), 4.42 (d, Jꢁ=ꢁ12.9 Hz, 1H), 4.33 (d, Jꢁ=ꢁ11.8 Hz,
1H), 4.24 (d, Jꢁ=ꢁ11.8 Hz, 1H), 3.84 (s, 3H), 2.86 (m, 2H), 2.73 (m, 2H),
1.93 (s, 3H), 1.79 (m, 4H); 13C NMR: δ 162.3, 161.3, 158.3, 156.4, 135.4,
130.6, 114.9, 58.8, 57.3, 55.6, 54.3, 28.5, 25.3, 24.5, 22.5, 21.8. Anal. Calcd
for C21H23Cl3N2O2S2Te: C, 39.69; H, 3.96; Cl, 16.74; N. 4.41. Found: C,
39.48; H, 3.79; Cl, 16.66; N, 4.35.
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350ꢀ
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