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

Mykola Kut; Mikhajlo Onysko; Vasyl Lendel

doi:10.1515/hc-2016-0169

Article Open Access

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

Mykola Kut , Mikhajlo Onysko and Vasyl Lendel

Published/Copyright: November 28, 2016

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From the journal Heterocyclic Communications Volume 22 Issue 6

Abstract

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-5Н-[1,3]thiazolo[3,2-а]thieno[2,3-d]pyrimidin-5-one hydrochlorides.

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 trichloride; regioselectivity

Introduction

Organotellurium compounds show anti-cancer [1], [2], [3], antioxidant [3], [4] and anti-bacterial activity [5] and are used in neuropathy [6], [7], [8], [9], [10], [11]. In this study we analyzed a new route of introduction of tellurium into a heterocyclic system. Electrophilic heterocyclization of unsaturated substrates under the action of tellurium tetrahalides is described for obtaining tellurium-containing fused heterocyclic systems [12], [13], [14]. Using for the same purpose aryltellurium trihalides is barely mentioned in the literature. Indeed, there are only few data about using aryltellurium trihalides in the reaction with unsaturated alcohols, phenols and acids [15], [16], [17], [18]. We choose the N-alkenyl derivatives of 5,6-disubstituted-2-thioxothieno[2,3-d]pyrimidin-4-one as the objects for study electrofilic heterocyclization by p-alkoxyphenyltellurium trihalides.

Results and discussion

5,6-Disubstituted-2-thioxothieno[2,3-d]pyrimidin-4-ones 1–6 were synthesized as shown in Scheme 1 and used subsequently as substrates for electrophilic heterocyclization in the presence of p-alkoxyphenyltellurium trihalides (Scheme 2). The model compounds 1–6 contain a few nucleophilic centers in the molecule, which provides an opportunity to study regioselectivity of the electrophilic cyclization. Although several cyclization pathways could be suggested (not shown), the reaction takes a single route indicated in Scheme 2.

Scheme 1

Synthesis of 5,6-disubstituted 2-thioxothieno[2,3-d]pyrimidin-4-ones 1–6.

Scheme 2

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.

The heterocyclization was successfully conducted in acetic acid, chloroform and acetonitrile at different temperatures. It was found that under the optimal conditions the electrophilic heterocyclization is conducted in acetic acid at room temperature. The tellurium-containing compounds 7–15 were regioselectively obtained as the only products. It can be suggested that the addition of aryltellurium trichloride to a double bond of 1–6 takes place to generate the intermediate product A which is a direct precursor to the final product 7–15. In one case the hydrochloride 14 was transformed into a free base 16 (Scheme 2) by treatment with sodium sulfite. This is a remarkable result because the expected reduction of tellurium was not observed. All products 1–16 were fully characterized by spectral methods and elemental analysis.

Conclusion

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 reaction is highly regioselective.

Experimental

¹H NMR (400 MHz) and ¹³C NMR (100 MHz) spectra were recorded in DMSO-d₆ on a Varian Mercury-400 instrument. Melting points were determined on a Stuart SMP30 instrument. Elemental analyses were performed on an Elementar Vario analyzer. All reagents were obtained from commercial suppliers and used without further purification. Anhydrous solvents were prepared according to the standard methods. The p-alkoxyphenyltellurium trihalides were synthesized according to the literature procedure [19].

Synthesis of 5,6-disubstituted 3-alkenyl-2-thioxothieno[2,3-d]pyrimidin-4-ones 1–6

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.

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-Dimethyl-3-(2-methylprop-2-en-1-yl)-2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one (2)

Yield 89%; mp 189–190°С; ¹H 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.

3-(Prop-2-en-1-yl)-2-thioxo-2,3,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-4(1H)-one (3)

Yield 85%.; mp 218–219°С; lit. mp 205–208°С [22].

3-(2-Methylprop-2-en-1-yl)-2-thioxo-2,3,5,6,7,8-hexahydro[1]benzothieno[2,3-d]pyrimidin-4(1H)-one (4)

Yield 85%.; mp 202–204°С; ¹H NMR: δ 13.56 (s, 1H), 4.85 (s, 2H), 4.72 (s, 1H), 4.42 (s, 1H), 2.75 (m, 2H), 2.64 (m, 2H), 1.77 (m, 4H), 1.72 (s, 3H); ¹³C NMR: δ 174.3, 156.7, 149.4, 139.4, 131.5, 129.1, 116.0, 109.3, 50.3, 25.4, 24.5, 23.0, 22.1, 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-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one (5)

Yield 85%; mp 223–224°С; ¹H NMR: δ 13.61 (s, 1H), 5.88 (m, 1H), 5.14 (s, 1H), 5.10 (d, J=6.5 Hz 1H), 4.96 (d, J=5.1 Hz, 2H), 2.82 (t, J=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.

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.

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

A mixture of 5,6-disubstituted 2-thioxothieno[2,3-d]pyrimidin-4-one 1–6 (1 mmol) and p-alkoxyphenyltellurium trichloride (1 mmol)in acetic acid (40 mL) was stirred at room temperature for 8 h. The resultant precipitate was filtered and crystallized from acetic acid.

6,7-Dimethyl-2-[dichloro(4-methoxyphenyl)tellurylmethyl]-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin-5-one hydrochloride (7)

Yield 73%; mp 201–202°С; ¹H NMR: δ 8.05 (d, J=8.9 Hz, 2H), 7.09 (d, J=8.9 Hz, 2H), 4.69 (m, 1H), 4.60 (dd, J=13.0 and 2.6 Hz, 1H), 4.38 (dd, J=12.9 and 7.2 Hz, 1H), 4.04 (dd, J=11.8 and 8.7 Hz, 1H), 3.91 (dd, J=13.0 and 2.6 Hz, 1 H), 3.82 (s, 3H), 2.32 (s, 6H); ¹³C NMR: δ 162.2, 158.8, 157.1, 135.9, 128.8, 128.7, 125.6, 119.7, 115.4, 56.0, 54.1, 49.9, 13.2. Anal. Calcd for C₁₈H₁₉Cl₃N₂O₂S₂Te: C, 36.31; H, 3.55; Cl, 17.86; N. 4.70. Found: C, 36.11; H, 3.39; Cl, 17.52; N, 4.58.

2,6,7-Trimethyl-2-(dichloro(4-methoxyphenyl)tellurylmethyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin-5-one hydrochloride (8)

Yield 73%; mp 206–207°С; ¹H NMR: δ 8.05 (d, J=8.9 Hz, 2H), 7.11 (d, J=9.0 Hz, 2H), 4.85 (d, J=12.9 Hz, 1H), 4.41 (d, J 12.9 Hz, 1H), 4.31 (d, J=11.9 Hz, 1H), 4.22(d, J 11.9 Hz, 1H), 3.81 (s, 3H), 2.34 (s, 6H), 1.91 (s, 3H); ¹³C NMR: δ 162.0, 161.7, 158.6, 157.1, 135.8, 129.0, 128.7, 125.6, 119.9, 115.4, 59.3, 57.8, 56.0, 54.6, 29.0, 13.2. Anal. Calcd for C₁₉H₂₁Cl₃N₂O₂S₂Te: C, 37.44; H, 3.80; Cl, 17.45; N. 4.60. Found: C, 37.19; H, 3.69; Cl, 17.28; N, 4.49.

6,7-Dimethyl-2-(dichloro(4-ethoxyphenyl)tellurylmethyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin-5-one hydrochloride (9)

Yield 73%; mp 217–218°С; ¹H NMR: δ 8.03 (d, J=8.8 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 4.68 (m, 1H), 4.60 (d, J=12.8 Hz, 1H), 4.38 (dd, J=12.8, 7.2 Hz, 1H), 4.09 (dt, J=10.5 and 5.2 Hz, 2H), 4.02 (d, J=8.6 Hz, 1H), 3.90 (dd, J=11.8 and 5.9 Hz, 1H), 2.33 (s, 6H), 1.34 (t, J=6.9 Hz, 3H); ¹³C NMR: δ 162.2, 161.0, 158.9, 157.2, 135.9, 128.8, 128.5, 125.3, 119.7, 115.8, 64.0, 54.1, 49.8, 15.0, 13.2. Anal. Calcd for C₁₉H₂₁Cl₃N₂O₂S₂Te: C, 37.44; H, 3.80; Cl, 17.45; N. 4.60. Found: C, 37.26; H, 3.62; Cl, 17.36; N, 4.45.

2,6,7-Trimethyl-2-(dichloro(4-ethoxyphenyl)tellurylmethyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]thieno[2,3-d]pyrimidin-5-one hydrochloride (10)

Yield 73%; mp 201–202°С; ¹H NMR: δ 8.03 (d, J=8.8 Hz, 2H), 7.10 (d, J=8.8 Hz, 2H), 4.85 (d, J=12.9 Hz, 1H), 4.41 (d, J=12.9 Hz, 1H), 4.30 (d, J=11.9 Hz, 1H), 4.22 (d, J=11.6 Hz, 1H), 4.09 (q, J=7.0 Hz, 1H), 2.34 (s, 6H), 1.91 (s, 3H), 1.34 (t, J=7.0 Hz, 3H); ¹³C NMR: δ 162.0, 161.0, 158.6, 157.1, 135.8, 129.0, 128.7, 125.3, 119.9, 115.7, 64.0, 59.3, 57.8, 54.6, 29.0, 15.0, 13.3, 13.1. Anal. Calcd for C₂₀H₂₃Cl₃N₂O₂S₂Te: C, 38.53; H, 4.04; Cl, 17.06; N. 4.49. Found: C, 38.35; H, 3.97; Cl, 16.96; N, 4.40.

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 (11)

Yield 74%.; mp 213–214°С; ¹H NMR: δ 8.05 (d, J=8.9 Hz, 2H), 7.10 (d, J=8.9 Hz, 2H), 4.69 (m, 1H), 4.61 (dd, J=13.1 and 2.6 Hz, 1H), 4.39 (dd, J=12.9 and 7.1, Hz, 1H), 4.04 (dd, J=11.8 and 8.7 Hz, 1H), 3.91 (dd, J=11.8 and 6.0 Hz, 1H), 2.83 (m, 2H), 2.71 (m, 2H), 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.

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%; mp 228–230°С; ¹H NMR: δ 8.07 (d, J=8.8 Hz, 2H), 7.13 (d, J=8.8 Hz, 2H), 4.86 (d, J=13.0 Hz, 1H), 4.42 (d, J=12.9 Hz, 1H), 4.33 (d, J=11.8 Hz, 1H), 4.24 (d, J=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.

2-(Dichloro(4-ethoxyphenyl)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 (13)

Yield 73%; mp 216–218°С; ¹H NMR: δ 8.04 (d, J=8.3 Hz, 2H), 7.08 (d, J=8.3 Hz, 2H), 4.71 (m, 1H), 4.58 (d, J=13.0 Hz, 1H), 4.40 (dd, J=12.0 and 7.7 Hz, 1H), 4.16–3.98 (m, 3H), 3.92 (dd, J=10.5 and 5.9 Hz, 1H), 2.83 (m, 2H), 2.70 (m, 2H), 1.77 (m, 4H), 1.35 (t, J=6.6 Hz, 3H); 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, 49.8, 25.7, 24.9, 23.0, 22.2, 15.0. Anal. Calcd for C₂₁H₂₃Cl₃N₂O₂S₂Te: C, 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-Methyl-2-(dichloro(4-ethoxyphenyl)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 (14)

Yield 73%; mp 208–209°С; ¹H NMR: δ 8.05 (d, J=7.4 Hz, 2H), 7.10 (d, J=7.8 Hz, 2H), 4.86 (d, J=12.9 Hz, 1H), 4.41 (d, J=13.0 Hz, 1H), 4.32 (d, J=11.5 Hz, 1H), 4.24 (d, J=11.6 Hz, 1H), 4.12 (q, J=7.0 Hz, 2H), 2.85(m, 2H), 2.72 (m, 2H), 1.93 (s, 3H), 1.78 (m, 4H), 1.35 (t, J=7.0 Hz, 3H); ¹³C NMR: δ 162.9, 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, 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.

2-Methyl-2-(dichloro(4-methoxyphenyl)tellurylmethyl)-2,3,7,8-tetrahydro-5H,6H-cyclopenta[4,5]thieno[2,3-d][1,3]thiazolo[3,2-a]pyrimidin-5-one hydrochloride (15)

Yield 70%; mp 180–181°С; ¹H NMR: δ 8.05 (d, J=8.9 Hz, 2H), 7.11 (d, J=8.9 Hz, 2H), 4.87 (d, J=12.9 Hz, 1H), 4.42 (d, J=12.9 Hz, 1H), 4.30 (d, J=11.9, Hz, 1H), 4.22 (d, J=11.9 Hz, 1H), 3.81(s, 3H), 2.88 (t, J=6.9 Hz, 4H), 2.41–2.30 (m, 2H), 1.91 (s, 3H); ¹³C NMR: δ 167.9, 158.4, 156.5, 139.7, 136.8, 135.8, 125.6, 116.7, 115.4, 59.2, 57.8, 56.0, 54.7, 29.5, 29.0, 28.8, 28.6, 27.9. Anal. Calcd 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.

Synthesis of 2-methyl-2-(dichloro(4-ethoxyphenyl)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 (16)

A solution of hydrochloride 14 (0.3 mmol) in DMSO (10 mL) was treated dropwise with a solution of sodium sulfite (1.2 mmol) in water (5 mL). The resultant white precipitate was filtered, washed with water and crystallized from acetic acid; yield 70%; mp 95–96°С; ¹H NMR: δ 7,67 (d, J=8.5 Hz, 3H), 6,80 (d, J=8.5 Hz, 3H), 4.38 (d, J=12.6 Hz, 2H), 4.00 (q, J=7 Hz, 3H), 3.49 (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, J=14.8 and 7.8 Hz, 6H); ¹³C NMR: δ 159.3, 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, 22.5, 15.2. Anal. Calcd for C₂₂H₂₄Cl₂N₂O₂S₂Te: C, 43.10; H, 4.2;, Cl, 11.57; N. 4.57. Found: C, 43.15; H, 4.39; Cl, 11.71; N, 4.61.

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Received: 2016-10-5

Accepted: 2016-10-31

Published Online: 2016-11-28

Published in Print: 2016-12-1

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Articles in the same Issue

https://doi.org/10.1515/hc-2016-0169

Keywords for this article

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 trichloride; regioselectivity

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