Molecules 2014, 19
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-CH2-O-CO), 4.51 (s, 2H, N-CH2-Triazole), 5.88 (s, 2H, O-CH2-Triazole), 7.45 (m, 4H, H-Aromatic),
7.73 (m, 2H, H-Aromatic), 7.84 (s, 1H, H-Triazole), 8.11 (dd, 1H, H-Aromatic), 8.54(dd, 2H,
H-Aromatic). 13C-NMR (CDCl3) δ 20.42(CH3), 49.13 (CH2-quinazoline), 59.78, 62.62 (-OCH2CH2O-),
67.69 (-O-CH2-N<), 123.51–133.80 (-CH-Aromatic), 142.13,146.46, 152.22 (C-Aromatic), 162.43,
(CO-Aromatic),172.12 (CO-Ester). ESI-MS(M+H)+, m/z calcd for C22H21N5O4 420.43, found 420.40.
4-(4-((2-Phenylquinazolin-4-yloxy)methyl)-1,2,3-triazol-1-yl)butylacetate (6c). Yield 83%; Rf 0.68;
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eluent CH2Cl2; H-NMR (CDCl3) δ 1.56 (s, 3H, -CO-CH3), 1.92 (m, 4H, -CH2-CH2-), 3.97 (t, 2H,
J = 6.3 Hz,-CH2-N(Triazole)), 4.29 (t, 2H, J = 7.2 Hz, -CH2-O-CO), 5.85 (s, 2H, O-CH2-C(Triazole)),
7.46 (m, 4H, H-Aromatic), 7.72 (m, 2H, H-Aromatic), 7.93 (s, 1H, H-Triazole), 8.10 (dd, 1H,
H-Aromatic), 8.56 (dd, 2H, H-Aromatic).13C-NMR (CDCl3) δ 18.61(CH3), 23.38, 24.71 (-CH2-CH2-)
47.62(-CH2-quinazoline), 57.67 (CH2-N(Triazole)), 61.06 (CH2-O), 123.59–133.77 (CH-Aromatic),
142.13, 146.46, 152.22 (C-Aromatic),163.86, (CO-Aromatic), 168.70 (CO-Ester). ESI-MS (M+H)+,
m/z calcd for C23H23N5O3 418.46, found 418.60.
3-((1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranos-1-yl)-1,2,3-triazol-4-yl)methyl)-2-methylquinazolin-4-one
1
(6d). Yield 83%; Rf 0.60; eluent CH2Cl2; H-NMR (CDCl3) δ 2.76 (s, 3H, -CH3), 4.54 (m, 1H, H5'),
4.65 (m, 1H, H5'), 4.81 (m, 1H, H4'), 5.23 (s, 2H, -CH2-), 6.10 (dd, 1H, J = 8.6 Hz, H3'), 6.19 (dd, 1H,
J = 8.6 Hz, H2'), 6.31(d, 1H, H1'), 7.23–7,40(m, 13H, H-Aromatic), 7.57(s, 1H, H-Triazole), 8.62–7.86
(m, 5H, H-Aromatic), 7.88 (m, 1H, H-Aromatic).13C-NMR (CDCl3) δ 23.67(CH3), 39.45, 63.75(CH2),
71.70 (C5'), 75.22 (C2'), 81.13 (C3'), 90.34 (C4'), 117.84 (C1'), 124.07–134.35 (CH-Aromatic),
140.73–159.53 (C-Aromatic), 162.51, 163.58 (CO). ESI-MS(M+H)+, m/z calcd for C38H31N5O8
686,68, found 686.50.
2-((4-((2-Methyl-4-oxoquinazolin-3-yl)methyl)-1,2,3-triazol-1-yl) methoxy) ethylacetate (6e). Yield
1
87%; Rf 0.59; eluent CH2Cl2; H-NMR (CDCl3) δ 1.9(s, 3H, -CO-CH3), 2.84 (s, 3H, Aromatic-CH3),
3.64 (t, 2H, -CH2-O), 4.35 (t, 2H, -CH2-O-CO), 4.52 (s, 2H, N-CH2-Triazole), 5.33 (s, 2H,
O-CH2-Triazole), 7.34–7.55 (m, 3H, H-Aromatic), 7.78 (s, 1H, H-Triazole), 8.13 (m, 1H, H-Aromatic).
13C-NMR (CDCl3) δ 20.23, 23.86 (CH3), 39.59 (CH2-quinazoline), 49.04, 62.16 (OCH2CH2O), 78.77
(O-CH2-N), 120.24–134.34 (CH-Aromatic), 143.00, 147.35, 154.36 (C-Aromatic), 162.01 (CO-Aromatic),
170.25 (CO-Ester). ESI-MS(M+H)+, m/z calcd for C17H19N5O4 358.36, found 358.40.
4-(4-((2-Methyl-4-oxoquinazolin-3-yl)methyl)-1,2,3-triazol-1-yl)butylacetate (6f). Yield 86%; Rf 0.60;
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eluent CH2Cl2; H-NMR (CDCl3) δ 1.55 (s, 3H, -CO-CH3), 1.90 (m, 4H,-CH2-CH2-), 2.83 (s, 3H,
Aromatic-CH3), 3.99 (t, 2H, J = 6.2Hz, -CH2-N(Triazole)), 4.27 (t, 2H, J = 7.2Hz, -CH2-O-CO), 5.29
(s, 2H, O-CH2-C(Triazole)), 7.20–7,52 (m, 3H, H-Aromatic), 7.63 (s, 1H, H-Triazole), 8.17 (m, 1H,
H-Aromatic). 13C-NMR (CDCl3) δ (ppm): 20.88, 23.74 (CH3), 25.67, 26.87 (CH2-CH2) 39.72
(CH2-quinazoline), 49.91 (CH2-N(Triazole)), 63.32 (CH2-O), 123.89–134.46(CH-Aromatic), 142.93,
147.42, 154.44 (C-Aromatic), 162.71, (CO-Aromatic), 168.70 (CO-Ester). ESI-MS(M+H)+, m/z calcd
for C18H21N5O3 356.39, found 356.40.
3-((1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranos-1-yl)-1,2,3-triazol-4-yl)methyl)quinazolin-4-one
(6g).
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Yield 84%; Rf 0.60; eluent CH2Cl2; H-NMR (CDCl3) δ (ppm): 4.68 (m, 1H, H5'), 4.75 (m, 1H, H5'),