Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
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Parham Foroumadi
und
Alireza Foroumadi
Abstract
An efficient, practical approach to the copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-one derivatives is described. The preparation involves treatment of benzyl amines with benzyl anthranilamides in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide (TBAB).
Introduction
Nitrogen-containing heterocyclic compounds are privileged structures in medicinal chemistry [[[1], [2], [3]. Quinazolin-4(3H)-one is a significant pharmacophore among nitrogen-containing heterocyclic compounds, due to the various biological and pharmacological properties. Anticancer 4], antimicrobial [5], anti-inflammatory [6], anticonvulsant [7], anti-ulcer [8], anti-bacterial [9] and aldose reductase inhibitory activity 10] are some of the biological properties of quinazolin-4(3H)-ones. Considering the remarkable biological activities of quinazolines [11], it is not surprising that many synthetic procedures have been reported, giving access to the libraries of this scaffold [[12], [13], [14], [15], [16], [17], [18], [19], [20]. Transition-metal coupling reactions form important approaches to this class of compounds by utilizing various substrates, including palladium-catalyzed carbonylation of 2-aminobenzamide 21], palladium-catalyzed isocyanide insertion/cyclization sequence between 2-aminobenzamides and aryl halides [22], C-H bond carboxamidation of N-arylamidines catalyzed by palladium acetate [23] and coupling reaction between 2-bromobenzoic acid and amidines catalyzed by CuI [24]. In our previous report, oxidative synthesis of 2-substituted quinazolin-4(3H)-ones starting from benzyl-substituted anthranilamides was described [25]. Surprisingly, it was found that 2,3-disubstituted quinazolin-4(3H)-ones are formed as the major products from the same substrates and benzylamines in the reaction conducted under similar conditions. This work is a continuation of our efforts directed toward the development of new heterocyclic chemistry [26], [27], [28], [29], [30], [31].
Results and discussion
A new pathway for the preparation of 2,3-disubstituted quinazolin-4(3H)-ones by the reaction of N-benzylanthranilamides 3a–h with benzylamines is shown in Scheme 1. The substrates 3a–h are easily prepared by treatment of isatoic anhydride (1) with benzylamines 2a–h in aqueous media. In order to optimize the reaction condition, the synthesis of 3-benzyl-2-phenylquinazolin-4(3H)-one (4a) was chosen as a model reaction. First, the effects of tetra-n-butylammonium bromide (TBAB) and Cu(OAc)2 were evaluated in this reaction in the presence of K2CO3 in p-xylene. The best yield of the product was obtained in the presence of 20 mol% of TBAB and 5 mol% of Cu(OAc)2. Different solvents including toluene, N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) were also investigated. However, these changes did not enhance the yield of the desired product as compared with the use of p-xylene. The important role of air in this reaction was demonstrated by performing the reaction under inert atmosphere, which led to trace amounts of the desired product only. As shown in Scheme 1, the reactions of aromatic benzylamines containing electron-donating groups, such as Me and OMe, or electron-withdrawing groups, such as F and Cl, furnish the corresponding products 4a–h in 61–77% yields. An attempted synthesis with aliphatic amines was not successful, however. The structures of all synthesized products were confirmed by analytical and spectral data including Fourier transform infrared spectroscopy (FT-IR), 1H NMR, 13C NMR and MS. For example, in the 1H NMR spectra the CH2 benzylic group for sterically unhindered molecules appears as a singlet. By contrast, the restricted rotation in 4e gives rise to the appearance of benzylic protons as an AB system with two doublets at δ 4.90 and 5.51.
Synthesis of compounds 4a–h from N-benzylanthranilamides.
As suggested in Scheme 2, the mechanism may involve coordination of Cu(II) with benzylamine followed by oxidation of the resultant complex 5 to benzylamine 6. A subsequent addition reaction of 3 with 6 may generate intermediate product 7 which is the final precursor to 4 [32], [33], [34].
Suggested mechanism for the synthesis of quinazolin-4(3H)-ones 4.
Conclusions
A straightforward, copper-catalyzed approach to the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl anthranilamides is described. The simplicity of the procedure, ready availability of the starting materials and good yields are the main advantages of this method.
Experimental
All commercially available chemicals and reagents were purchased from Merck or Fluka and were used without further purification. Melting points were measured with a Koffler hot stage apparatus and are uncorrected. 1H NMR (500 MHz) and 13C NMR (125 MHz) spectra were recorded on a Bruker FT-500 spectrometer in DMSO-d6, using tetramethylsilane (TMS) as an internal standard. IR spectra were recorded on a Shimadzu 470 spectrophotometer in KBr disks. electron ionization (EI) mass spectra were obtained using an Agilent Technology (HP) mass spectrometer operating at an ionization potential of 70 eV. EA was performed using an Elemental Analysen system.
General procedure for the synthesis of N-benzylanthranilamides 3a–h
A mixture of isatoic anhydride 1 (1 mmol) and benzylamine 2a–h (1 mmol) in H2O (10 mL) was stirred at room temperature. Upon completion of the reaction, as monitored by thin-layer chromatography (TLC), the resulting precipitate was filtered, washed with cold water, dried and crystallized from ethanol to afford the desired compound 3a–h.
General procedure for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones 4a–h
A mixture of N-benzylanthranilamide 3a–h (1 mmol), Cu(OAc)2 (5 mol%), K2CO3 (1 mmol) and TBAB (20 mol%) in p-xylene (10 mL) was stirred for 24 h under reflux. Upon completion of the reaction, as indicated by TLC analysis, the mixture was cooled and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (4:1) to afford pure product 4a–h.
3-Benzyl-2-phenylquinazolin-4(3H)-one (4a)
This compound was obtained as a white solid; yield 65%; mp 150–152°C (lit mp 152–153°C, [19], [35], [36]); IR: 2949, 1682, 1567, 1271 cm−1; 1H NMR (DMSO-d6): δ 8.22 (d, J=8.0 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.72 (d, J=8.0 Hz, 1H), 7.59 (t, J=8.0 Hz, 1H), 7.51–7.40 (m, 5H), 7.24–7.18 (m, 3H), 6.92–6.90 (m, 2H), 5.18 (s, 2H); 13C NMR (DMSO-d6): δ 161.9, 156.6, 147.4, 137.2, 135.6, 135.2, 130.2, 128.9, 128.7, 128.4, 127.8, 127.7, 127.5, 126.9, 126.7, 120.8, 48.7. Anal. Calcd for C21H16N2O: C, 80.75; H, 5.16; N, 8.97. Found: C, 80.56; H, 5.35; N, 9.14.
3-(4-Methoxybenzyl)-2-(4-methoxyphenyl)quinazolin-4(3H)-one (4b)
This compound was obtained as a white solid; yield 77%; mp 158–160°C; IR: 3061, 2952, 1677, 1577, 1266 cm−1; 1H NMR (CDCl3): δ 8.36 (d, J=7.3 Hz, 1H), 7.81–7.76 (m, 2H), 7.54–7.51 (m, 1H), 7.35 (d, J=8.7 Hz, 2H), 6.95 (d, J=8.7 Hz, 2H), 6.90 (d, J=8.7 Hz, 2H), 6.75 (d, J=8.7 Hz, 2H), 5.26 (s, 2H), 3.87 (s, OCH3), 3.77 (s, OCH3); 13C NMR (CDCl3): δ 162.4, 161.0, 158.9, 156.5, 134.6, 132.3, 130.6, 129.8, 129.6, 129.2, 128.6, 128.3, 127.7, 127.1, 120.6, 117.4, 55.4, 55.2, 48.4; MS: m/z (%) 372 (M+, 31), 341 (19), 265 (43), 145 (100), 121 (59), 77 (25). Anal. Calcd for C23H20N2O3: C, 74.18; H, 5.41; N, 7.52. Found: C, 73.89; H, 5.67; N, 7.76.
3-(4-Methylbenzyl)-2-(p-tolyl)quinazolin-4(3H)-one (4c)
This compound was obtained as a white solid; yield 72%; mp 144–146°C; IR: 3053, 2948, 1566, 1273 cm−1; 1H NMR (CDCl3): δ 8.36 (d, J=7.9 Hz, 1H), 7.78–7.77 (m, 2H), 7.53–7.50 (m, 1H), 7.29 (d, J=7.9 Hz, 2H), 7.23 (d, J=7.9 Hz, 2H), 7.01 (d, J=7.9 Hz, 2H), 6.87 (d, J=7.9 Hz, 2H), 5.25 (s, CH2), 2.42 (s, CH3), 2.29 (s, CH3); 13C NMR (CDCl3): δ 162.5, 156.7, 147.2, 140.1, 137.1, 134.5, 133.6, 132.4, 129.2, 129.2, 128.0, 127.4, 127.1, 127.0, 126.9, 120.8, 48.7, 21.4, 21.0; MS: m/z (%) 340 (M+, 22), 325 (31), 311 (12), 235 (71), 145 (100), 91 (19), 77 (34). Anal. Calcd for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found: C, 81.00; H, 5.74; N, 8.41.
3-(4-Fluorobenzyl)-2-(4-fluorophenyl)quinazolin-4(3H)-one (4d)
This compound was obtained as a white solid; yield 61%; mp 171–173°C; IR: 3064, 2966, 1667, 1572, 1256 cm−1; 1H NMR (CDCl3): δ 8.33 (d, J=8.5 Hz, 1H), 7.73–7.71 (m, 1H), 7.68 (d, J=8.6 Hz, 1H), 7.35–7.32 (m, 3H), 7.14–7.11 (m, 3H), 6.89–6.80 (m, 3H), 5.31 (s, 2H); 13C NMR (CDCl3): δ 164.6, 162.6 (d, JC-F=175 Hz), 161.2 (d, JC-F=124 Hz), 155.4, 145.5, 135.1, 133.2, 131.9, 131.1, 130.2 (d, JC-F=7.8 Hz), 129.3, 128.8 (d, JC-F=7.8 Hz), 126.5, 121.8, 115.8 (d, JC-F=21.4 Hz), 115.5 (d, JC-F=21.7 Hz), 48.2; MS: m/z (%) 348 (M+, 44), 239 (73), 144 (100), 109 (62), 95 (41). Anal. Calcd for C21H14F2N2O: C, 72.41; H, 4.05; N, 8.04. Found: C, 72.60; H, 4.23; N, 7.86.
3-(2-Chlorobenzyl)-2-(2-chlorophenyl)quinazolin-4(3H)-one (4e)
This compound was obtained as a white solid; yield 70%; mp 176–178°C; IR: 3063, 2962, 1673, 1572, 1277 cm−1; 1H NMR (DMSO-d6): δ 8.30 (d, J=8.0 Hz, 1H), 7.92 (t, J=8.0 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 7.66 (t, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.51 (t, J=8.5 Hz, 1H), 7.36–7.30 (m, 3H), 7.24–7.20 (m, 2H), 7.02 (d, J=7.5 Hz, 1H), 5.51 (d, J=16.5 Hz, 1H), 4.90 (d, J=16.5 Hz, 1H); 13C NMR (DMSO-d6): δ 161.0, 152.8, 146.8, 134.8, 133.3, 132.9, 131.4, 131.3, 131.1, 129.8, 129.3, 128.9, 128.7, 128.6, 127.6, 127.4, 127.2, 127.1, 126.5, 120.4, 45.0; MS: m/z (%) 383 (M++2, 10), 381 (M+, 33), 269 (28), 145 (100), 125 (29), 111 (58), 76 (44). Anal. Calcd for C21H14Cl2N2O: C, 66.16; H, 3.70; N, 7.35. Found: C, 66.00; H, 3.49; N, 7.54.
3-(4-Chlorobenzyl)-2-(4-chlorophenyl)quinazolin-4(3H)-one (4f)
This compound was obtained as a white solid; yield 72%; mp 164–166°C; IR: 3054, 2962, 1666, 1559, 1258 cm−1; 1H NMR (DMSO-d6): δ 8.22 (d, J=8.0 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.59 (t, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H), 7.47 (d, J=8.0 Hz, 2H), 7.28 (d, J=8.0 Hz, 2H), 6.90 (d, J=8.0 Hz, 2H), 5.16 (s, 2H); 13C NMR (DMSO-d6): δ 161.3, 154.9, 146.8, 135.5, 134.7, 134.6, 133.7, 131.8, 129.8, 128.3, 128.2, 127.3 (2C), 126.4 (2C), 120.3, 47.6; MS: m/z (%) 383 (M++2, 15), 381 (M+, 40), 345 (55), 269 (61), 144 (100), 124 (44), 76 (29). Anal. Calcd for C21H14Cl2N2O: C, 66.16; H, 3.70; N, 7.35. Found: C, 66.38; H, 3.89; N, 7.19.
3-(3,4-Dichlorobenzyl)-2-(3,4-dichlorophenyl)quinazolin-4(3H)-one (4g)
This compound was obtained as a white solid; yield 63%; mp 160–162°C; IR: 3064, 2968, 1677, 1564, 1256 cm−1; 1H NMR (DMSO-d6): δ 8.23 (d, J=8.0 Hz, 1H), 7.88 (t, J=7.0 Hz, 1H), 7.73–7.70 (m, 2H), 7.66 (d, J=2.0 Hz, 1H), 7.62 (t, J=7.5 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.44 (dd, J=8.0, 1.5 Hz, 1H), 7.24 (s, 1H), 6.99 (d, J=8.0 Hz, 1H), 5.12 (s, 2H); 13C NMR (DMSO-d6): δ 161.30, 153.49, 146.67, 137.61, 135.14, 134.69, 132.68, 131.13, 131.01, 130.52, 130.45, 130.17, 129.78, 128.88, 128.08, 127.40, 127.30, 126.76, 126.34, 120.47, 47.33; MS: m/z (%) 454 (M++4, 11), 452 (M++2, 16), 450 (M+, 43), 303 (41), 159 (51), 144 (100), 77 (34). Anal. Calcd for C21H12Cl4N2O: C, 56.03; H, 2.69; N, 6.22. Found: C, 55.86; H, 2.85; N, 6.44.
2-(Furan-2-yl)-3-(furan-2-ylmethyl)quinazolin-4(3H)-one (4h)
This compound was obtained as a white solid; yield 65%; mp 173–175°C; IR: 3057, 2946, 1664, 1571, 1263 cm−1; 1H NMR (CDCl3): δ 8.33 (d, J=8.1 Hz, 1H), 7.78–7.74 (m, 1H), 7.66 (d, J=1.3 Hz, 1H), 7.51 (dd, J=5.4, 2.8 Hz, 1H), 7.49 (dd, J=5.6, 2.6 Hz, 1H), 7.29 (d, J=1.3 Hz, 1H), 7.14 (d, J=3.4 Hz, 1H), 6.60 (dd, J=3.6, 1.8 Hz, 1H), 6.25 (dd, J=3.2, 1.8 Hz, 1H), 6.16 (d, J=3.2 Hz, 1H), 5.26 (s, 2H); 13C NMR (CDCl3): δ 162.04, 149.60, 147.32, 147.20, 145.83, 144.43, 142.26, 134.55, 127.57, 127.25, 127.12, 120.65, 115.63, 111.99, 110.44, 108.44, 41.13; MS: m/z (%) 292 (M+, 29), 225 (50), 145 (100), 82 (47), 67 (33). Anal. Calcd for C17H12N2O3: C, 69.86; H, 4.14; N, 9.58. Found: C, 69.98; H, 4.09; N, 9.66.
Supplementary information (online only)
Characterization of compounds 3a–h.
Acknowledgments
This study was supported by the research council of Kerman University of Medical Sciences, Grant no: 95000218.
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/hc-2018-0051).
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Artikel in diesem Heft
- Frontmatter
- Preliminary Communications
- Antioxidant, α-glucosidase inhibitory and in vitro antitumor activities of coumarin-benzothiazole hybrids
- Synthesis and properties of tetracyanoquinodimethane derivatives
- Research Articles
- Synthesis, characterization and computational studies of 2-cyano-6-methoxybenzothiazole as a firefly-luciferin precursor
- Synthesis of fluorine-containing phthalocyanines and investigation of the photophysical and photochemical properties of the metal-free and zinc phthalocyanines
- Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
- Synthesis and mass spectrometric fragmentation pattern of 6-(4-chlorophenyl)-N-aryl-4-(trichloromethyl)-4H-1,3,5-oxadiazin-2-amines
- An efficient cascade synthesis of substituted 6,9-dihydro-1H-pyrazolo[3,4-f]quinoline- 8-carbonitriles
- Synthesis and antimicrobial evaluation of isoxazole-substituted 1,3,4-oxadiazoles
Artikel in diesem Heft
- Frontmatter
- Preliminary Communications
- Antioxidant, α-glucosidase inhibitory and in vitro antitumor activities of coumarin-benzothiazole hybrids
- Synthesis and properties of tetracyanoquinodimethane derivatives
- Research Articles
- Synthesis, characterization and computational studies of 2-cyano-6-methoxybenzothiazole as a firefly-luciferin precursor
- Synthesis of fluorine-containing phthalocyanines and investigation of the photophysical and photochemical properties of the metal-free and zinc phthalocyanines
- Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
- Synthesis and mass spectrometric fragmentation pattern of 6-(4-chlorophenyl)-N-aryl-4-(trichloromethyl)-4H-1,3,5-oxadiazin-2-amines
- An efficient cascade synthesis of substituted 6,9-dihydro-1H-pyrazolo[3,4-f]quinoline- 8-carbonitriles
- Synthesis and antimicrobial evaluation of isoxazole-substituted 1,3,4-oxadiazoles
