2.1.3. General Procedure for the Synthesis of (1,2,3-Triazole)Acetaldehyde Diethyl Acetals 10a–f

To a solution of azide 11 (1 mmol) in ethanol (1 mL) and water (1 mL), CuSO4 × H2O (0.1 mmol) and sodium ascorbate (0.05 mmol) were added, and these were followed by the respective alkyne 12a–f (1 mmol). The suspension was microwave-irradiated in the Plazmatronika RM microwave reactor (30 W) at 40–45 °C for 1 h. After cooling, the solvent was removed in vacuo and the residue was suspended in chloroform (5 mL) and filtered through a layer of Celite. The obtained solution was concentrated in vacuo, and the crude product was chromatographed on a silica gel with a methylene chloride–methanol mixture (200:1, 100:1 and 50:1, v/v) to give the respective pure 1,2,3-triazole 10a–f.

1-(2,2-Diethoxyethyl)-4-Phenyl-1H-1,2,3-Triazole (10a)

Yield 94%; colourless oil; IR (film, cm−1) νmax 3135, 3099, 3033, 2977, 2930, 2896, 1611, 1484, 1467, 1442, 1375, 1229, 1158, 1126, 1067; 1H NMR (200 MHz, CDCl3) δ 7.87–7.81 (m, 3H), 7.48–7.36 (m, 3H), 4.81 (t, J = 5.5 Hz, 1H), 4.50 (d, J = 5.4 Hz, 2H), 3.84–3.80 (m, 2H), 3.59–3.54 (m, 2H), 1.19 (t, J = 7.0 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 147.67, 130.69, 128.87, 128.13, 157.73, 121.06, 101.02, 63.94, 53.98, 15.24. Anal. Calcd. for C14H19N3O2: C, 64.35; H, 7.33; N, 16.08. Found: C, 64.53; H, 7.67; N, 15.95.

1-(2,2-Diethoxyethyl)-4-(2-Fluorophenyl)-1H-1,2,3-Triazole (10b)

Yield 89%; colourless oil; IR (film, cm−1) νmax 3154, 3072, 2978, 2931, 2897, 1804, 1746, 1583, 1557, 1487, 1376, 1234, 1220, 1126, 1072; 1H NMR (600 MHz, CDCl3) δ 8.31–8.27 (m, 1H), 8.05 (d, J = 3.8 Hz, 1H), 7.32–7.28 (m, 1H), 7.27–7.23 (m, 2H), 7.16–7.12 (m, 1H), 4.81 (t, J = 5.5 Hz, 1H), 4.51 (d, J = 5.5 Hz, 2H), 3.79–3.73 (m, 2H), 3.53–3.47 (m, 2H), 1.19 (t, J = 7.1 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 159.25 (d, J = 247.5 Hz), 141.07 (d, J = 2.1 Hz), 129.25 (d, J = 7.8 Hz), 127.80 (d, J = 3.3 Hz), 124.59 (d, J = 3.3 Hz), 124.21 (d, J = 13.1 Hz), 118.68 (d, J = 12.1 Hz), 115.69 (d, J = 22.1 Hz), 100.97, 63.88, 52.92, 15.19. Anal. Calcd. for C14H18N3O2F: C, 60.20; H, 6.50; N, 15.04. Found: C, 60.53; H, 6.72; N, 14.82.

1-(2,2-Diethoxyethyl)-4-(3-Fluorophenyl)-1H-1,2,3-Triazole (10c)

Yield 80%; colourless oil; IR (film, cm−1) νmax 3405, 3138, 2978, 2932, 2897, 1788, 1750, 1620, 1590, 1485, 1468, 1447, 1376, 1153, 1127, 1069; 1H NMR (600 MHz, CDCl3) δ 7.88 (s, 1H), 7.61–7.58 (m, 1H), 7.57–7.54 (m, 1H), 7.41–7.37 (m, 1H), 7.05–7.02 (m, 1H), 4.80 (t, J = 5.4 Hz, 1H), 4.50 (d, J = 5.3 Hz, 2H), 3.79–3.73 (m, 2H), 3.54–3.49 (m, 2H), 1.19 (t, J = 7.0 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 163.20 (d, J = 245.4 Hz), 146.58, 132.85 (d, J = 8.9 Hz), 130.44 (d, J = 7.7 Hz), 121.45, 121.30 (d, J = 2.1 Hz), 114.91 (d, J = 21.4 Hz), 112.64 (d, J = 23.1 Hz), 100.87, 63.92, 52.97, 15.23. Anal. Calcd. For C14H18N3O2F: C, 60.20; H, 6.50; N, 15.04. Found: C, 60.14; H, 6.67; N, 15.00.

1-(2,2-Diethoxyethyl)-4-(4-Fluorophenyl)-1H-1,2,3-Triazole (10d)

Yield 90%; colourless oil; IR (film, cm−1) νmax 3140, 2979, 2897, 1801, 1612, 1561, 1498, 1459, 1228, 1157, 1127, 1069; 1H NMR (200 MHz, CDCl3) δ 7.84–7.76 (m, 3H), 7.16–7.07 (m, 2H), 4.80 (t, J = 5.4 Hz, 1H), 4.49 (d, J = 5.3 Hz, 2H), 3.80–3.69 (m, 2H), 3.59–3.47 (m, 2H), 1.19 (t, J = 7.0 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 162.66 (d, J = 246.6 Hz), 146.80, 127.44 (d, J = 8.5 Hz), 126.95 (d, J = 3.3 Hz), 120.78, 115.81 (d, J = 21.9 Hz), 100.92, 63.85, 52.95, 15.21. Anal. Calcd. For C14H18N3O2F: C, 60.20; H, 6.50; N, 15.04. Found: C, 60.33; H, 6.62; N, 15.17.

1-(2,2-Diethoxyethyl)-4-(2,4-Difluorophenyl)-1H-1,2,3-Triazole (10e)

Yield 91%; colourless oil; IR (film, cm−1) νmax 3424, 3157, 2976, 2928, 1800, 1625, 1601, 1494, 1418, 1145, 1130, 1053; 1H NMR (600 MHz, CDCl3) δ 8.29–8.24 (m, 1H), 8.00 (d, J = 3.8 Hz, 1H), 7.00–6.99 (m, 1H), 6.92–6.88 (m, 1H), 4.80 (t, J = 5.4 Hz, 1H), 4.51 (d, J = 5.4 Hz, 2H), 3.79–3.73 (m, 2H), 3.54–3.48 (m, 2H), 1.19 (t, J = 7.0 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 162.53 (dd, J = 250.2 Hz, J = 12.2 Hz), 159.29 (dd, J = 250.9 Hz, J = 12.1 Hz), 140.43, 128.86 (dd, J = 9.8 Hz, J = 5.4 Hz), 123.68 (d, J = 12.6 Hz), 115.19 (dd, J = 13.3 Hz, J = 4.3 Hz), 111.96 (dd, J = 21.0 Hz, J = 3.4 Hz), 104.08 (dd, J = 25.3 Hz, J = 26.4 Hz), 100.90, 63.28, 52.94, 15.16. Anal. Calcd. for C14H17N3O2F2: C, 56.56; H, 5.76; N, 14.03. Found: C, 56.65; H, 5.48; N, 13.92.

1-(2,2-Diethoxyethyl)-4-(4-Fluoro-3-Methylphenyl)-1H-1,2,3-Triazole (10f)

Yield 80%; colourless oil; IR (film, cm−1) νmax 3355, 3136, 2978, 2930, 2896, 1804, 1557, 1495, 1459, 1120, 1061; 1H NMR (200 MHz, CDCl3) δ 7.80 (s, 1H), 7.72–7.66 (m, 1H), 7.62–7.53 (m, 1H), 7.10–7.00 (m, 1H), 7.72–7.66 (m, 1H), 4.80 (t, J = 5.4 Hz, 1H), 4.48 (d, J = 5.3 Hz, 2H), 3.84–3.68 (m, 2H), 3.56–3.43 (m, 2H), 2.32 (d, J = 1.9 Hz, 3H), 1.19 (t, J = 7.0 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 161.24 (d, J = 245.5 Hz), 146.98, 128.87 (d, J = 5.5 Hz), 126.52 (d, J = 3.2 Hz), 125.39 (d, J = 17.6 Hz), 124.72 (d, J = 15.2 Hz), 120.74, 115.42 (d, J = 23.1 Hz), 100.96, 63.91, 52.95, 15.23, 14.61 (d, J = 3.3 Hz). Anal. Calcd. for C15H20N3O2F: C, 61.42; H, 6.87; N, 14.32. Found: C, 61.35; H, 7.01; N, 14.09.

2.1.4. General Procedure for the Synthesis of Nitrones 8a–f and 9a–f

A solution of the respective diethyl acetal 10a–f (0.1 mmol) in 1M HCl (1 mL) was stirred at reflux for 1 h. After that, the solvent was removed and the residue re-evaporated with water until a neutral pH was obtained. The obtained aldehyde 13a–f was immediately used in the next step without further purification. To a solution of the obtained aldehyde 13a–f in ethanol (2 mL), CH3CO2Na (1.3 mmol) and N-alkyhydoxylamine hydrochloride (1.1 mmol) were added. The reaction mixture was stirred until the disappearance of the starting aldehyde was noticed on TLC. After that 10% NaHCO3 was added (5 mL) and the product was extracted with methylene chloride (3 × 5 mL). Organic extracts were combined, dried (MgSO4), concentrated, and crystallized to give the respective pure nitrone 8a–f or 9a–f.

N-(2-(4-Phenyl-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8a)

Yield 69%; white amorphous solid; mp 97–8 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3406, 3115, 3084, 3060, 2964, 1614, 1484, 1462, 1437, 1225, 1204, 1148, 1077, 1048; 1H NMR (600 MHz, CDCl3) δ 8.00 (s, 1H), 7.84–7.81 (m, 2H), 7.44–7.41 (m, 2H), 7.36–7.33 (m, 1H), 7.18–7.17 (m, 1H), 5.39–5.36 (m, 2H), 3.79 (d, J = 0.7 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 148.16, 131.93, 130.29, 128.88, 128.34, 125.80, 121.01, 52.76, 45.71. Anal. Calcd. for C11H12N4O: C, 61.10; H, 5.59; N, 25.92. Found: C, 60.91; H, 5.51; N, 25.70.

N-(2-(4-(2-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8b)

Yield 63%; white amorphous solid; mp 125–6 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3425, 3176, 3094, 3060, 3006, 1617, 1583, 1556, 1488, 1469, 1425, 1393, 1318, 1239, 1213, 1073; 1H NMR (600 MHz, CDCl3) δ 8.29–8.25 (m, 1H), 8.11 (d, J = 3.6 Hz, 1H), 7.33–7.30 (m, 1H), 7.27–7.23 (m, 1H), 7.18–7.12 (m, 2H), 5.42–5.40 (m, 2H), 3.79 (d, J = 0.8 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 159.29 (d, J = 248.6 Hz), 141.60 (d, J = 2.1 Hz), 132.04, 129.53 (d, J = 8.6 Hz), 127.84 (d, J = 3.5 Hz), 124.61 (d, J = 3.3 Hz), 123.93 (d, J = 12.5 Hz), 118.30 (d, J = 12.9 Hz), 115.73 (d, J = 21.8 Hz), 52.70, 46.02. Anal. Calcd. for C11H11N4OF: C, 56.41; H, 4.73; N, 23.92. Found: C, 56.73; H, 4.56; N, 24.11.

N-(2-(4-(3-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8c)

Yield 61%; white amorphous solid; mp 158–160 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3424, 3133, 3095, 2871, 1621, 1589, 1561, 1484, 1229, 1181; 1H NMR (600 MHz, D2O) δ 8.31 (s, 1H), 7.55–7.50 (m, 2H), 7.47–7.44 (m, 1H), 7.43–7.39 (m, 1H), 7.10–7.07 (m, 1H), 5.38–5.34 (d, J = 4.2 Hz, 2H), 3.69 (d, J = 0.7 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 163.22 (d, J = 246.2 Hz), 147.05, 132.48 (d, J = 9.2 Hz), 131.54, 130.46 (d, J = 8.1 Hz), 121.45, 121.40 (d, J = 2.9 Hz), 115.15 (d, J = 21.0 Hz), 112.75 (d, J = 23.0 Hz), 52.83, 45.63. Anal. Calcd. For C11H11N4OF: C, 56.41; H, 4.73; N, 23.92. Found: C, 56.26; H, 4.43; N, 23.96.

N-(2-(4-(4-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8d)

Yield 78%; white amorphous solid; mp 165–7 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3363, 3203, 3134, 2877, 2382, 1614, 1562, 1499, 1458, 1238, 1158, 1093; 1H NMR (600 MHz, D2O) δ 8.33 (s, 1H), 7.81–7.78 (m, 2H), 7.63–7.61 (m, 1H), 7.26–7.22 (m, 2H), 5,47–5.42 (m, 2H), 3.78 (s, 3H); 13C NMR (151 MHz, CDCl3) δ 162.80 (d, J = 247.6 Hz), 147.27, 131.68, 127.54 (d, J = 7.8 Hz), 126.54 (d, J = 3.3 Hz), 120.81, 115.87 (d, J = 21.8 Hz), 52.81, 45.61. Anal. Calcd. for C11H11N4OF: C, 56.41; H, 4.73; N, 23.92. Found: C, 56.52; H, 4.82; N, 23.83.

N-(2-(4-(2,4-Difluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8e)

Yield 56%; white amorphous solid; mp 122–3 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3424, 3179, 3094, 3058, 1619, 1599, 1459, 1412, 1397, 1268, 1126, 1067; 1H NMR (600 MHz, D2O) δ 8.36 (d, J = 2.9 Hz, 1H), 7.99–7.94 (m, 1H), 7.63 (t, J = 5.0 Hz, 1H), 7.13–7.08 (m, 2H), 5.47 (d, J = 4.8 Hz, 2H), 3.78 (s, 3H); 13C NMR (151 MHz, CDCl3) δ 162.69 (dd, J = 250.8 Hz, J = 13.1 Hz), 159.33 (dd, J = 250.9 Hz, J = 12.2 Hz), 140.92 (d, J = 2.8 Hz), 131.73, 128.82 (dd, J = 9.8 Hz, J = 5.4 Hz), 123.48 (d, J = 11.9 Hz), 114.79 (dd, J = 13.1 Hz, J = 3.2 Hz), 112.03 (dd, J = 22.0 Hz, J = 3.5 Hz), 104.16 (dd, J = 26.4 Hz, J = 25.2 Hz), 52.76, 45.93. Anal. Calcd. for C11H10N4OF2 × 0.25H2O: C, 51.46; H, 4.12; N, 21.83. Found: C, 51.60; H, 3.85; N, 21.74.

N-(2-(4-(4-Fluoro-3-Methylphenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)Methanamine Oxide (8f)

Yield 61%; white amorphous solid; mp 171–3 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3171, 3130, 2882, 159, 1448, 1461, 1237, 1211, 1168, 1121; 1H NMR (600 MHz, D2O) δ 8.20 (s, 1H), 7.57–7.48 (m, 3H), 7.08–7.05 (m, 1H), 5,35–5.33 (d, J = 5.2 Hz, 2H), 3.69 (s, 3H), 2.20 (s, 3H); 13C NMR (151 MHz, CDCl3) δ 161.36 (d, J = 246.5 Hz), 147.46, 131.87, 128.95 (d, J = 5.6 Hz), 126.11 (d, J = 4.3 Hz), 125.47 (d, J = 17.6 Hz), 124.78 (d, J = 7.8 Hz), 120.77, 115.48 (d, J = 23.05 Hz), 52.82, 45.64, 14.58 (d, J = 3.3 Hz). Anal. Calcd. for C12H13N4OF: C, 58.06; H, 5.28; N, 22.57. Found: C, 57.78; H, 4.99; N, 22.61.

2-Methyl-N-(2-(4-Phenyl-1H-1,2,3-Triazol-1-yl)Ethylidene)Propan-2-Amine Oxide (9a)

Yield 85%; white amorphous solid; mp 91–3 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3375, 3328, 3134, 2973, 2872, 1611, 1470, 1442, 1363, 1118, 1085, 1052, 1001; 1H NMR (600 MHz, CDCl3) δ 7.98 (s, 1H), 7.86–7.81 (m, 2H), 7.48–7.29 (m, 4H), 5.39 (d, 2H, J = 5.4 Hz), 1.53 (s, 9H); 13C NMR (151 MHz, CDCl3): 148.12, 130.39, 128.86, 128.29, 127.21, 125.80, 120.94, 70.68, 46.73, 27.87. Anal. Calcd. for C14H18N4O: C, 65.09; H, 7.02; N, 21.69. Found: C, 64.93; H, 6.87; N, 21.96.

N-(2-(4-(2-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9b)

Yield 39%; white amorphous solid; mp 72–3 °C (recrystallized from ethyl ether—petroleum ether); IR (KBr, cm−1) νmax 3417, 3137, 2974, 1625, 1583, 1488, 1390, 1220, 1109, 1076; 1H NMR (600 MHz, CDCl3) δ 8.28–8.25 (m, 1H), 8.09 (d, J = 3.6 Hz, 1H), 7.33–7.20 (m, 3H), 7.15–7.11 (m, 1H), 5.40 (d, J = 4.9 Hz, 2H), 1.52 (s, 9H); 13C NMR (151 MHz, CDCl3) δ 159.29 (d, J = 247.5 Hz), 141.55 (d, J = 3.3 Hz), 129.48 (d, J = 7.8 Hz), 127.83 (d, J = 4.0 Hz), 127.43, 124.60 (d, J = 3.3 Hz), 123.90 (d, J = 12.8 Hz), 118.37 (d, J = 12.5 Hz), 115.70 (d, J = 22.0 Hz), 70.62, 47.05, 27.85. Anal. Calcd. For C14H17N4OF×0.5H2O: C, 58.93; H, 6.36; N, 19.64. Found: C, 58.99; H, 6.49; N, 19.51.

N-(2-(4-(3-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9c)

Yield 30%; white amorphous solid; mp 94–5 °C (recrystallized from methylene chloride—ethyl ether); IR (KBr, cm−1) νmax 3417, 3127, 2975, 1620, 1589, 1485, 1460, 1392, 1364, 1227; 1H NMR (600 MHz, CDCl3) δ 8.00 (s, 1H), 7.60–7.55 (m, 2H), 7.41–7.37 (m, 1H), 7.30–7.28 (m, 1H), 7.05–7.02 (m, 1H), 5.38 (d, J = 5.2 Hz, 2H), 1.53 (s, 9H); 13C NMR (151 MHz, CDCl3) δ 163.21 (d, J = 245.6 Hz), 146.99 (d, J = 2.7 Hz), 132.58 (d, J = 8.4 Hz), 130.44 (d, J = 8.6 Hz), 126.86, 121.38, 121.38, 115.08 (d, J = 21.3 Hz), 112.73 (d, J = 23.1 Hz), 70.76, 46.64, 27.87. Anal. Calcd. For C14H17N4OF×1.5H2O: C, 55.43; H, 6.65; N, 18.48. Found: C, 55.16; H, 6.63; N, 18.36.

N-(2-(4-(4-Fluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9d)

Yield 37%; white amorphous solid; mp 128–131 °C (recrystallized from ethyl ether); IR (KBr, cm−1) νmax 3425, 2975, 2533, 1613, 1562, 1499, 1227, 1158; 1H NMR (600 MHz, CDCl3) δ 7.95 (s, 1H), 7.82–7.79 (m, 2H), 7.30–7.27 (m, 1H), 7.14–7.11 (m, 2H), 5.38 (d, J = 5.2 Hz, 2H), 1.53 (s, 9H); 13C NMR (151 MHz, CDCl3) δ 162.78 (d, J = 247.6 Hz), 147.23, 127.53 (d, J = 7.6 Hz), 126.98, 126.63 (d, J = 3.6 Hz), 120.73, 115.86 (d, J = 22.1 Hz), 70.73, 46.64, 27.88. Anal. Calcd. for C14H17N4OF×0.5H2O: C, 58.93; H, 6.36; N, 19.64. Found: C, 58.94; H, 6.17; N, 19.85.

N-(2-(4-(2,4-Difluorophenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9e)

Yield 43%; white amorphous solid; mp 122–3 °C (recrystallized from ethyl ether); IR (KBr, cm−1) νmax 3425, 3167, 2923, 1629, 1599, 1562, 1396, 1211, 1131, 1073; 1H NMR (600 MHz, CDCl3) δ 8.29–8.24 (m, 1H), 8.06 (d, J = 3.6 Hz, 1H), 7.28–7.26 (m, 1H), 7.02–6.98 (m, 1H), 6.93–6.88 (m, 1H), 5.40 (d, J = 5.0 Hz, 2H), 1.53 (s, 9H); 13C NMR (151 MHz, CDCl3) δ 162.67 (dd, J = 249.8 Hz, J = 12.1 Hz), 159.32 (dd, J = 251.3 Hz, J = 10.9 Hz), 140.88 (d, J = 2.7 Hz), 128.84 (dd, J = 9.2 Hz, J = 4.7 Hz), 127.13, 123.44 (d, J = 12.2 Hz), 114.86 (d, J = 13.2 Hz), 112.03 (dd, J = 21.1 Hz, J = 3.2 Hz), 104.16 (dd, J = 25.3 Hz, J = 25.4 Hz), 70.66, 46.99, 27.86. Anal. Calcd. for C14H16N4OF2×0.25H2O: C, 56.27; H, 5.57; N, 18.76. Found: C, 56.56; H, 5.41; N, 18.68.

N-(2-(4-(4-Fluoro-3-Methylphenyl)-1H-1,2,3-Triazol-1-yl)Ethylidene)-2-Methylpropan-2-Amine Oxide (9f)

Yield 78%; white amorphous solid; mp 104–7 °C (recrystallized from ethyl ether); IR (KBr, cm−1) νmax 3406, 3128, 3100, 2978, 1495, 1468, 1393, 1309, 1281, 1209, 1082; 1H NMR (600 MHz, D2O) δ 7.92 (s, 1H), 7.70–7.68 (m, 1H), 7.59–7.57 (m, 1H), 7.29–7.27 (m, 1H), 7.07–7.03 (m, 1H), 5.37 (d, J = 5.2 Hz, 2H), 2.32 (d, J = 1.8 Hz, 3H), 1.53 (s, 9H); 13C NMR (151 MHz, CDCl3) δ 161.35 (d, J = 246.5 Hz), 147.42, 128.95 (d, J = 5.6 Hz), 127.16, 126.23 (d, J = 3.3 Hz), 125.44 (d, J = 18.1 Hz), 124.79 (d, J = 7.7 Hz), 120.67, 115.45 (d, J = 23.2 Hz), 70.70, 46.67, 27.87, 14.55 (d, J = 3.3 Hz). Anal. Calcd. for C15H19N4OF×0.25H2O: C, 61.10; H, 6.67; N, 19.01. Found: C, 60.80; H, 6.70; N, 19.29.