Home One-pot three-component synthesis of substituted 2-(1,2,3-triazol-1-yl)pyrimidines from pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones
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One-pot three-component synthesis of substituted 2-(1,2,3-triazol-1-yl)pyrimidines from pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones

  • Zheng-Jun Quan EMAIL logo , Miao-Miao Wang , Liang-Jie Yang , Yu-Xia Da , Zhang Zhang and Xi-Cun Wang EMAIL logo
Published/Copyright: January 23, 2014
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 20 Issue 1

Abstract

New 2-(1,2,3-triazol-1-yl)pyrimidines were synthesized in good yields by the three-component reaction of pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones in the presence of K2CO3 at room temperature. This procedure eliminates the need to handle organic azides in the synthesis of analogous compounds.

Keywords: methylene ketones; pyrimidines; pyrimidin-2-yl sulfonates; three-component reaction; 1,2,3-triazoles

Introduction

Since the copper(I)-catalyzed azide-alkyne cycloaddition was reported independently by the groups of Sharpless and Meldal, the synthesis of 1,4- and 1,5-disubstituted 1,2,3-triazoles have attracted a great deal of attention due to their potential biological activities [1]. In recent years, 1,4,5-trisubstituted 1,2,3-triazoles have found important applications in medicinal chemistry [2–5]. A few methods for the synthesis of fully substituted 1,2,3-triazoles have been described [6]. One of the most attractive approaches to the synthesis of these compounds is the direct Pd- or Cu-catalyzed arylation of 1,4-disubstituted triazoles with aryl halides [7–12]. Transition metal-catalyzed reactions for the chemoselective and regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from organic azides and alkyl iodides or bromides have also been developed [13–16]. Another access to these compounds is the highly regioselective 1,3-dipolar cycloaddition between an azide and an enamine [17]. 1,4,5-Trisubstituted 1,2,3-triazoles can also be obtained by treatment of aryl azides with ketones in the presence of amines [18–20].

In our previous reports [21, 22], we have described an efficient protocol for the synthesis of C2-substituted pyrimidines by cross-coupling reaction of readily available pyrimidin-2-yl sulfonates with N-, S-, O- and C-nucleophiles. In this work, the synthesis of polysubstituted 2-(1,2,3-triazol-1-yl)pyrimidines by the reaction of pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones is described.

Conditions for the three-component reaction were explored using pyrimidin-2-yl sulfonate (1a), NaN3 and ethyl acetoacetate (2a) as the substrates (Scheme 1) and various base catalysts. In the presence of Et3N and Et2NH in acetone, product 3a was obtained in only 10% and 17% yield, respectively. By contrast, in the presence of inorganic bases, namely K2CO3, K3PO4, NaOH and KOH in acetone product 3a was obtained in the respective yields of 81%, 53%, 19% and 54%. The yields were also significantly affected by solvents. For example, the reactions conducted in acetonitrile, ethanol, DMF and DMSO in the presence of K2CO3 delivered 3a in the respective yields of 54%, 15%, 60% and 66%. Traces of 3a were obtained for the reaction conducted in dichloromethane. The best result was obtained when the reaction was conducted in acetone in the presence of 1.2 equivalent amounts of K2CO3.

Scheme 1
Scheme 1

Various pyrimidin-2-yl sulfonates (1) were allowed to react with NaN3 and ethyl acetoacetate (2a) under optimized conditions (Scheme 1). In general, good yields were obtained under the standard reaction conditions. Methyl acetoacetate (2b) and pentane-2,4-dione (2c) were also used to further explore the scope of the synthesis of the triazolylpyrimidines. As expected, the desired products 3f–n were obtained smoothly in good to excellent yields (Scheme 1; see Supplementary material online). The structures of all products are fully consistent with their spectral data and that for 3j was unambiguously assigned by using X-ray diffraction analysis (Figure 1). Crystallographic data for the structure analysis have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication, CCDC No. CCDC 944956 for 3j. Copies of this information can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: ).

Figure 1 The single crystal X-ray crystallographic structure of product 3j.
Figure 1

The single crystal X-ray crystallographic structure of product 3j.

Experimental details

Melting points were determined on an XT-4 electrothermal micromelting point apparatus and are uncorrected. 1H NMR (400 MHz) spectra and 13C NMR (100 MHz) spectra were recorded in CDCl3 on a Varian Mercury plus-400 instrument. IR spectra were recorded using KBr pellets on Nicolet Avatar 360 spectrophotometer. Electron-impact mass spectra were recorded at 70 eV on a TRACE DSQ instrument. Elemental analyses were performed on a Carlo-Erba 1106 Elemental Analysis instrument. X-Ray diffraction data were recorded using a Rigaku Mercury CCDC area detector with graphite monochromated Mo Kα radiation. Column chromatography was performed on silica gel (300–400 mesh). Commercially available reagents were used without further purification.

General procedure for the synthesis of 2-(1,2,3-triazol-1-yl)pyrimidines 3a–n

A mixture of a pyrimidin-2-yl sulfonate (1, 0.5 mmol), NaN3 (1.0 mmol), a methylene ketone (2, 1.0 mmol), K2CO3 (1.2 mmol) and acetone (5 mL) was stirred at room temperature for 24 h. After complete consumption of the starting material, as evidenced by TLC analysis, the mixture was quenched with saturated NH4Cl aqueous solution (5 mL) and extracted with diethyl ether (2 × 10 mL). The combined extracts were washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on silica gel eluting with petroleum ether/ethyl acetate (5:1) to provide product 3.

Ethyl 2-[4-(ethoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl]-4-methyl-6-phenylpyrimidine-5-carboxylate (3a)

Yellow oil; yield 81%; 1H NMR: δ 7.74 (q, J = 8.0 Hz, 2H, ArH), 7.55–7.50 (m, 3H, ArH), 4.48 (q, J = 8.0 Hz, 2H, CH2), 4.28 (q, J = 8.0 Hz, 2H, CH2), 2.98 (s, 3H, CH3), 2.77 (s, 3H, CH3), 1.45 (t, J = 8.0 Hz, 3H, CH3), 1.13 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 168.8, 166.9, 165.6, 161.6, 154.2, 140.6, 137.3, 136.2, 131.1, 128.8, 128.5, 125.4, 62.4, 61.2, 22.8, 14.4, 13.7, 11.5; IR: 2980, 1722, 1542, 1428, 1251, 1089 cm-1; EI-MS: m/z 395 (M+). Anal. Calcd for C20H21N5O4: C, 60.75; H, 5.35; N, 17.71. Found: C, 60.90; H, 5.40; N, 17.62.

Ethyl 2-[4-(ethoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl]-4-methyl-6-p-tolylpyrimidine-5-carboxylate (3b)

White solid; mp 36–37°C; yield 70%; 1H NMR: δ 7.65 (d, J = 8.0 Hz, 2H, ArH), 7.30 (d, J = 8.0 Hz, 2H, ArH), 4.48 (q, J = 8.0 Hz, 2H, CH2), 4.31 (q, J = 8.0 Hz, 2H, CH2), 2.97 (s, 3H, CH3), 2.75 (s, 3H, CH3), 2.43 (s, 3H, CH3), 1.45 (t, J = 8.0 Hz, 3H, CH3), 1.19 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 168.6, 167.2, 165.4, 161.6, 154.2, 141.7, 140.5, 137.2, 133.3, 129.7, 128.5, 125.2, 62.4, 61.2, 22.8, 21.5, 14.4, 13.7, 11.5; IR: 1722, 1578, 1542, 1425, 1251, 1089 cm-1; EI-MS: m/z 409 (M+). Anal. Calcd for C21H23N5O4: C, 61.60; H, 5.66; N, 17.10. Found: C, 61.72; H, 5.60; N, 17.19.

Ethyl 2-[4-(ethoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl]-4-(4-methoxyphenyl)-6-methylpyrimidine-5-carboxylate (3c)

Yellow solid; mp 85–86°C; yield 78%; 1H NMR: δ 7.75 (d, J = 8.0 Hz, 2H, ArH), 7.01 (d, J = 8.0 Hz, 2H, ArH), 4.49 (q, J = 8.0 Hz, 2H, CH2), 4.34 (q, J = 8.0 Hz, 2H, CH2), 3.89 (s, 3H, CH3), 2.98 (s, 3H, CH3), 2.74 (s, 3H, CH3), 1.46 (t, J = 8.0 Hz, 3H, CH3), 1.23 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 168.4, 167.4, 164.7, 162.2, 161.7, 154.1, 140.5, 137.2, 130.4, 128.4, 124.7, 114.3, 62.4, 61.2, 55.5, 22.8, 14.4, 13.8, 11.5; IR: 2980, 1722, 1542, 1428, 1254, 1089 cm-1; EI-MS: m/z 425 (M+). Anal. Calcd for C21H23N5O5: C, 59.29; H, 5.45; N, 16.46. Found: C, 59.17; H, 5.51; N, 16.54.

Ethyl 4-(4-chlorophenyl)-2-(4-(ethoxycarbonyl)-5-methyl-1H- 1,2,3-triazol-1-yl)-6-methylpyrimidine-5-carboxylate (3d)

Yellow oil; yield 76%; 1H NMR: δ 7.68 (t, J = 8.0 Hz, 2H, ArH), 7.47 (t, J = 8.0 Hz, 2H, ArH), 4.45 (q, J = 8.0 Hz, 2H, CH2), 4.29 (q, J = 8.0 Hz, 2H, CH2), 2.95 (s, 3H, CH3), 2.74 (s, 3H, CH3), 1.42 (t, J = 8.0 Hz, 3H, CH3), 1.17 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 169.0, 166.7, 164.3, 161.5, 154.2, 140.5, 137.6, 137.3, 134.6, 129.9, 129.1, 125.3, 62.6, 61.2, 22.9, 14.3, 13.7, 11.5; IR: 2980, 1722, 1542, 1428, 1248, 1089 cm-1; EI-MS: m/z 429 (M+). Anal. Calcd for C20H20ClN5O4: C, 55.88; H, 4.69; N, 16.29. Found: C, 55.61; H, 4.74; N, 16.20.

Ethyl 2-[4-(ethoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl]-4-(4-fluorophenyl)-6-methylpyrimidine-5-carboxylate (3e)

Yellow oil; yield 78%; 1H NMR: δ 7.73–7.70 (m, 2H, ArH), 7.17–7.13 (m, 2H, ArH), 4.43 (q, J = 8.0 Hz, 2H, CH2), 4.26 (q, J = 8.0 Hz, 2H, CH2), 2.93 (s, 3H, CH3), 2.71 (s, 3H, CH3), 1.39 (t, J = 8.0 Hz, 3H, CH3), 1.14 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 168.8, 166.8, 165.7, 164.3, 163.2, 161.5, 154.1, 140.5, 137.2, 132.3, 130.8, 125.2, 116.1, 115.9, 62.5, 61.2, 14.3, 13.7, 11.4; IR: 2980, 1722, 1542, 1431, 1251, 1092 cm-1; EI-MS: m/z 413 (M+). Anal. Calcd for C20H20FN5O4: C, 58.11; H, 4.88; N, 16.94. Found: C, 58.24; H, 4.83; N, 17.03.

Ethyl 2-(4-(methoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl)-4-methyl-6-phenylpyrimidine-5-carboxylate (3f)

Yellow oil; yield 73%; 1H NMR: δ 7.73–7.71 (m, 2H, ArH), 7.53–7.49 (m, 3H, ArH), 4.26 (q, J = 8.0 Hz, 2H, CH2), 3.98 (s, 3H, CH3), 2.98 (s, 3H, CH3), 2.75 (s, 3H, CH3), 1.11 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 168.8, 166.9, 165.6, 161.9, 154.2, 140.8, 137.0, 136.2, 131.1, 128.8, 128.5, 125.4, 62.4, 52.1, 22.8, 13.6, 11.5; IR: 2950, 1722, 1578, 1542, 1437, 1251, 1092 cm-1; EI-MS: m/z 381 (M+). Anal. Calcd for C19H19N5O: C, 59.84; H, 5.02; N, 18.36. Found: C, 59.99; H, 4.96; N, 18.51.

Ethyl 2-[4-(methoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl]-4-methyl-6-p-tolylpyrimidine-5-carboxylate (3g)

Yellow solid; mp 88–90°C; yield 90%; 1H NMR: δ 7.63 (d, J = 8.0 Hz, 2H, ArH), 7.28 (d, J = 8.0 Hz, 2H, ArH), 4.28 (q, J = 8.0 Hz, 2H, CH2), 3.97 (s, 3H, CH3), 2.96 (s, 3H, CH3), 2.72 (s, 3H, CH3), 2.41 (s, 3H, CH3), 1.16 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 168.6, 167.1, 165.4, 161.9, 154.1, 141.7, 140.7, 136.9, 133.3, 129.6, 128.5, 125.2, 62.4, 52.1, 22.8, 21.5, 13.7, 11.5; IR: 2980, 1722, 1578, 1542, 1437, 1251, 1092 cm-1; EI-MS: m/z 395 (M+). Anal. Calcd for C20H21N5O: C, 60.75; H, 5.35; N, 17.71. Found: C, 60.87; H, 5.31; N, 17.79.

Ethyl 4-(4-chlorophenyl)-2-(4-(methoxycarbonyl)-5-methyl-1H- 1,2,3-triazol-1-yl)-6-methylpyrimidine-5-carboxylate (3h)

Colorless oil; yield 62%; 1H NMR: δ 7.69 (d, J = 8.0 Hz, 2H, ArH), 7.48 (d, J = 8.0 Hz, 2H, ArH), 4.30 (q, J = 8.0 Hz, 2H, CH2), 3.99 (s, 3H, CH3), 2.97 (s, 3H, CH3), 2.75 (s, 3H, CH3), 1.19 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 169.0, 166.7, 164.3, 161.9, 154.2, 140.7, 137.6, 137.1, 134.6, 129.9, 129.2, 125.3, 62.6, 52.1, 22.9, 13.7, 11.5; IR: 2974, 1725, 1578, 1542, 1434, 1251, 1092 cm-1; EI-MS: m/z 415 (M+). Anal. Calcd for C19H18ClN5O4: C, 54.88; H, 4.36; N, 16.84. Found: C, 54.75; H, 4.41; N, 16.92.

Ethyl 4-(4-fluorophenyl)-2-[4-(methoxycarbonyl)-5-methyl-1H- 1,2,3-triazol-1-yl]-6-methylpyrimidine-5-carboxylate (3i)

Yellow oil; yield 77%; 1H NMR: δ 7.75–7.72 (m, 2H, ArH), 7.19–7.15 (m, 2H, ArH), 4.28 (q, J = 8.0 Hz, 2H, CH2), 3.97 (s, 3H, CH3), 2.95 (s, 3H, CH3), 2.73 (s, 3H, CH3), 1.15 (t, J = 8.0, 3H, CH3); 13C NMR: δ 168.9, 166.8, 165.8, 164.4, 163.2, 161.9, 154.1, 140.7, 137.0, 132.3 (d), 130.8 (d), 125.2, 116.2, 115.9, 62.5, 52.1, 22.8, 13.7, 11.4; IR: 2956, 1722, 1542, 1434, 1251, 1089 cm-1; EI-MS: m/z 399 (M+). Anal. Calcd for C19H18FN5O4: C, 57.14; H, 4.54; N, 17.54. Found: C, 57.26; H, 4.50; N, 17.44.

Ethyl 2-[4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl]-4-methyl-6-phenylpyrimidine-5-carboxylate (3j)

Yellow solid; mp 94–96°C; yield 83%; 1H NMR: δ 7.75–7.73 (m, 2H, ArH), 7.55–7.50 (m, 3H, ArH), 4.28 (q, J = 8.0 Hz, 2H, CH2), 2.97 (s, 3H, CH3), 2.78 (s, 6H, CH3), 1.13 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 194.5, 168.8, 166.9, 165.6, 154.2, 143.8, 139.1, 136.2, 131.1, 128.8, 128.5, 125.4, 62.5, 28.4, 22.8, 13.7, 11.5; IR: 2980, 1725, 1686, 1569, 1542, 1425, 1248, 1083 cm-1; EI-MS: m/z 365 (M+). Anal. Calcd for C19H19N5O3: C, 62.46; H, 5.24; N, 19.17. Found: C, 62.32; H, 5.27; N, 19.26.

Ethyl 2-(4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl)-4-methyl-6-p- tolylpyrimidine-5-carboxylate (3k)

Yellow oil; yield 68%; 1H NMR: δ 7.64 (d, J = 8.0 Hz, 2H, ArH), 7.28 (d, J = 8.0 Hz, 2H, ArH), 4.29 (q, J = 8.0 Hz, 2H, CH2), 2.95 (s, 3H, CH3), 2.74 (d, J = 8.0 Hz, 6H, CH3), 2.41 (s, 3H, CH3), 1.17 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 194.4, 168.5, 167.1, 165.4, 154.2, 143.8, 141.7, 139.0, 133.3, 129.5, 128.5, 125.1, 62.4, 28.3, 22.8, 21.4, 13.7, 11.4; IR: 2980, 1725, 1686, 1569, 1542, 1425, 1248, 1080 cm-1; EI-MS: m/z 379 (M+). Anal. Calcd for C20H21N5O3: C, 63.31; H, 5.58; N, 18.46. Found: C, 63.20; H, 5.64; N, 18.61.

Ethyl 2-(4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl)-4-(4-methoxyphenyl)-6-methylpyrimidine-5-carboxylate (3l)

Yellow solid; mp 128–130°C; yield 70%; 1H NMR: δ 7.74 (d, J = 8.0 Hz, 2H, ArH), 6.99 (d, J = 8.0 Hz, 2H, ArH), 4.32 (q, J = 8.0 Hz, 2H, CH2), 3.87 (s, 3H, CH3), 2.95 (s, 3H, CH3), 2.76 (s, 3H, CH3), 2.72 (s, 3H, CH3), 1.21 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 194.5, 168.4, 167.4, 164.7, 162.2, 154.1, 143.8, 138.9, 130.4, 128.4, 124.6, 114.3, 62.4, 55.5, 28.3, 22.7, 13.8, 11.4; IR: 2974, 1722, 1686, 1569, 1542, 1425, 1251, 1080 cm-1; EI-MS: m/z 395 (M+). Anal. Calcd for C20H21N5O: C, 60.75; H, 5.35; N, 17.71. Found: C, 60.90; H, 5.41; N, 17.63.

Ethyl 2-(4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl)-4-(4-chlorophenyl)-6-methylpyrimidine-5-carboxylate (3m)

Yellow oil; yield 65%; 1H NMR: δ 7.69 (d, J = 8.0 Hz, 2H, ArH), 7.48 (d, J = 8.0 Hz, 2H, ArH), 4.31 (q, J = 8.0 Hz, 2H, CH2), 2.95 (s, 3H, CH3), 2.73 (t, J = 8.0 Hz, 6H, CH3), 1.20 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 194.4, 168.9, 166.7, 164.3, 154.2, 143.9, 139.0, 137.6, 134.6, 129.9, 129.1, 125.3, 62.59, 28.3, 22.8, 13.7, 11.4; IR: 2974, 1725, 1686, 1542, 1428, 1245, 1083 cm-1; EI-MS: m/z 399 (M+). Anal. Calcd for C19H18ClN5O3: C, 57.07; H, 4.54; N, 17.52. Found: C, 57.18; H, 4.58; N, 17.59.

Ethyl 2-(4-acetyl-5-methyl-1H-1,2,3-triazol-1-yl)-4-(4-fluorophenyl)-6-methylpyrimidine-5-carboxylate (3n)

Yellow oil; yield 72%; 1H NMR: δ 7.77 (q, J = 8.0 Hz, 2H, ArH), 7.20 (t, J = 8.0 Hz, 2H, ArH), 4.31 (q, J = 8.0 Hz, 2H, CH2), 2.96 (s, 3H, CH3), 2.77 (d, J = 8.0 Hz, 6H, CH3), 1.19 (t, J = 8.0 Hz, 3H, CH3); 13C NMR: δ 194.5, 168.9, 166.9, 165.8, 164.4, 163.3, 154.2, 143.9, 139.0, 132.3 (d), 130.8 (d), 125.2, 116.2, 115.9, 62.6, 22.9, 13.8, 11.5; IR: 2980, 1722, 1686, 1542, 1425, 1245, 1083 cm-1; EI-MS: m/z 383 (M+). Anal. Calcd for C19H18FN5O3: C, 59.52; H, 4.73; N, 18.27. Found: C, 59.41; H, 4.79; N, 18.35.

Corresponding authors: Zheng-Jun Quan and Xi-Cun Wang, Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, China, Gansu 730070, P.R. China; and Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Anning East Road 967#, Lanzhou, Gansu 730070, P.R. China, e-mail: ;

We are thankful for the financial support from the NSFC (Nos. 21362032, 21362031 and 21062017), the NSF of Gansu Province (No. 1208RJYA083), and the Scientific and Technological Innovation Engineering program of NWNU (Nos. nwnu-kjcxgc-03-64, nwnulkqn-10-15).

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Received: 2013-10-16
Accepted: 2013-11-26
Published Online: 2014-01-23
Published in Print: 2014-02-01

©2014 by Walter de Gruyter Berlin Boston

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

  2. Frontmatter
  3. Preliminary Communication
  4. One-pot three-component synthesis of substituted 2-(1,2,3-triazol-1-yl)pyrimidines from pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones
  5. Research Articles
  6. A convenient synthesis of 5,5′-bi-1,2,4-triazines via direct S-arylation and its application in the synthesis of 2,2′-bipyridines
  7. An efficient approach to the key intermediate of rosuvastatin
  8. Synthesis and properties of multifunctional hindered amine light stabilizers
  9. Tertiary formylated amines by microwave irradiation of N,N-dimethyl-N′-(2-pyridyl)formamidines with methyl vinyl ketone
  10. Synthesis and antimicrobial activity of some novel 2-thienyl substituted heterocycles
  11. Synthesis of 2-amino-5-mercapto-1,3,4-thiadiazole derivatives
  12. An easy and efficient protocol for the condensation reaction of isatin and N-substituted isatins with 1,2-diaminobenzene using low cost reusable clay catalyst
  13. Synthesis and antimicrobial activities of novel 6-(1,3-thiazol-4-yl)-1,3-benzoxazol-2(3H)-one derivatives
  14. A concise and efficient synthesis of (+)-preussin
  15. Synthesis, X-ray structural characterization, NLO, MEP, NBO and HOMO-LUMO analysis using DFT study of Zn(II)bis(3,4 dimethoxybenzoate)bis(nicotinamide) dihydrate
https://doi.org/10.1515/hc-2013-0175
Keywords for this article
methylene ketones; pyrimidines; pyrimidin-2-yl sulfonates; three-component reaction; 1,2,3-triazoles
Creative Commons
BY-NC-ND 3.0

Articles in the same Issue

  2. Frontmatter
  3. Preliminary Communication
  4. One-pot three-component synthesis of substituted 2-(1,2,3-triazol-1-yl)pyrimidines from pyrimidin-2-yl sulfonates, sodium azide and active methylene ketones
  5. Research Articles
  6. A convenient synthesis of 5,5′-bi-1,2,4-triazines via direct S-arylation and its application in the synthesis of 2,2′-bipyridines
  7. An efficient approach to the key intermediate of rosuvastatin
  8. Synthesis and properties of multifunctional hindered amine light stabilizers
  9. Tertiary formylated amines by microwave irradiation of N,N-dimethyl-N′-(2-pyridyl)formamidines with methyl vinyl ketone
  10. Synthesis and antimicrobial activity of some novel 2-thienyl substituted heterocycles
  11. Synthesis of 2-amino-5-mercapto-1,3,4-thiadiazole derivatives
  12. An easy and efficient protocol for the condensation reaction of isatin and N-substituted isatins with 1,2-diaminobenzene using low cost reusable clay catalyst
  13. Synthesis and antimicrobial activities of novel 6-(1,3-thiazol-4-yl)-1,3-benzoxazol-2(3H)-one derivatives
  14. A concise and efficient synthesis of (+)-preussin
  15. Synthesis, X-ray structural characterization, NLO, MEP, NBO and HOMO-LUMO analysis using DFT study of Zn(II)bis(3,4 dimethoxybenzoate)bis(nicotinamide) dihydrate
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