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Helvetica Chimica Acta – Vol. 95 (2012)
1H-NMR (CDCl3): 3.70 (s, OH, exchangeable with D2O); 3.91 – 3.93 (m, NCH2); 4.44 – 4.50 (m, CHOH);
4.53 (dd, J ¼ 6.3, 13.8, 1 H, ArOCH2); 4.65 (dd, J ¼ 3.6, 13.8, 1 H, ArOCH2); 5.49 (s, NOCH2); 6.70 (d,
J ¼ 8.8, 1 arom. H); 7.03 (d, J ¼ 8.8, 1 arom. H); 7.20 – 7.38 (m, 5 arom. H); 7.55 – 7.82 (m, 4 arom. H); 8.18
(s, HꢀC(5) of triazole). 13C-NMR (CDCl3): 52.46; 67.54; 68.68; 70.66; 115.20; 120.55; 121.30; 122.47;
124.68; 125.74; 128.05; 128.18; 128.50; 128.81; 129.23; 129.37; 130.38; 131.59; 134.32; 139.60; 140.69;
142.50; 151.70; 152.79; 164.97. MS: 494.09 (4.6, Mþ). Anal. calc. for C25H20Cl2N4O3 (495.36): C 60.62, H
4.07, Cl 14.31, N 11.31; found: C 60.76, H 4.17, Cl 14.20, N 11.23.
9H-Fluoren-9-one O-({1-[2-Hydroxy-3-(4-methoxyphenoxy)propyl]-1H-1,2,3-triazol-4-yl}methyl)-
oxime (7h). Purified by CC (SiO2; AcOEt/hexane 2 :1). Yield 0.69 g (76%). Yellow oil. Rf (AcOEt/
hexane 8 :1) 0.47. IR (film): 3370 (br.), 3045s, 2971m, 1665s, 1502m, 1450s, 1235s. 1H-NMR (CDCl3): 3.61
(s, MeO); 3.75 – 3.79 (complex, NCH2, OH); 4.32 – 4.34 (m, CHOH); 4.39 (dd, J ¼ 0.9, 7.0, 1 H, ArOH2);
4.51 (dd, J ¼ 1.9, 13.5, 1 H, ArOCH2); 5.39 (s, NOCH2); 6.65 – 6.68 (m, 4 arom. H); 7.11 – 7.15 (m, 4 arom.
H); 7.23 – 7.27 (m, 2 arom. H); 7.44 – 7.47 (m, 2 arom. H); 7.72 (s, HꢀC(5) of triazole). 13C-NMR (CDCl3):
53.02; 55.63; 60.40; 68.78; 69.59; 114.65; 115.49; 119.78; 119.86; 121.68; 124.97; 127.85; 128.23; 129.44;
129.99; 130.35; 131.08; 135.28; 140.26; 141.32; 144.22; 152.20; 152.83; 154.24. MS: 456.18 (0.5, Mþ). Anal.
calc. for C26H24N4O4 (456.49): C 68.41, H 5.30, N 12.27; found: C 68.53, H 5.35, N 12.18.
9H-Fluoren-9-one O-[(1-{2-Hydroxy-3-[4-(phenylmethyl)phenoxy]propyl}-1H-1,2,3-triazol-4-yl)-
methyl]oxime (7i). Purified by CC (SiO2; AcOEt/hexane 2 :1). Yield 0.72 g (70%). Pale-yellow solid.
Rf (AcOEt/hexane 8 :1) 0.68. M.p. 107 – 1098. IR (KBr): 3300 (br.), 3058s, 2945m, 1670s, 1500m, 1452s,
1
1210s. H-NMR ((D6)DMSO): 3.81 (s, PhCH2); 3.85 – 3.87 (m, NCH2); 4.23 (s, OH, exchangeable with
D2O); 4.40 (dd, J ¼ 7.4, 13.8, 1 H, ArOH2); 4.55 (dd, J ¼ 3.9, 13.8, 1 H, ArOCH2); 5.47 (s, NOCH2); 5.53 –
5.56 (m, CHOH); 6.79 – 6.82 (m, 2 arom. H); 7.04 – 7.47 (m, 11 arom. H); 7.80 – 7.85 (m, 3 arom. H); 8.12 –
8.14 (m, 1 arom. H); 8.24 (s, HꢀC(5) of triazole). 13C-NMR ((D6)DMSO): 39.46; 52.63; 67.75; 68.72;
69.51; 114.41; 120.55; 121.32; 125.72; 125.77; 128.17; 128.29; 128.56; 128.49; 128.82; 129.41; 129.60; 130.36;
131.56; 133.49; 134.37; 139.21; 139.62; 140.70; 141.61; 142.45; 151.71; 156.58. MS: 516.22 (6.1, Mþ). Anal.
calc. for C32H28N4O3 (516.59): C 74.40, H 5.46, N 10.85; found: C 74.54, H 5.40, N 10.92.
9H-Fluoren-9-one O-({1-[2-Hydroxy-3-(naphthalen-2-yloxy)propyl]-1H-1,2,3-triazol-4-yl}methyl)-
oxime (7j). Purified by CC (SiO2; AcOEt/hexane 2 :1). Yield 0.73 g (77%). White solid. Rf (AcOEt/
hexane 8 :1) 0.56. M.p. 158 – 1608. IR (KBr): 3410 (br.), 3050m, 2934m, 1665s, 1507m, 1479m, 1285s.
1H-NMR ((D6)DMSO): 4.05 – 4.07 (m, NCH2); 4.31 (s, OH, exchangeable with D2O); 4.48 (dd, J ¼ 7.3,
13.6, 1 H, ArOCH2); 4.63 (dd, J ¼ 3.8, 13.8, 1 H, ArOCH2); 5.49 (s, NOCH2); 5.62 – 5.64 (m, CHOH);
7.28 – 7.45 (m, 8 arom. H); 7.75 – 7.82 (m, 6 arom. H); 8.12 (s, 1 arom. H); 8.29 (s, HꢀC(5) of triazole).
13C-NMR ((D6)DMSO): 52.65; 67.74; 68.73; 69.57; 106.75; 118.60; 120.53; 121.32; 123.61; 125.76; 125.83;
126.15; 126.34; 126.64; 127.44; 128.17; 128.50; 128.82; 129.26; 129.39; 130.37; 131.57; 134.14; 134.34;
139.61; 140.69; 142.48; 151.71; 156.18. MS: 476.18 (0.6, Mþ). Anal. calc. for C29H24N4O3 (476.53): C 73.09,
H 5.08, N 11.76; found: C 73.23, H 5.01, N 11.87.
Diphenylmethanone O-({1-[2-Hydroxy-3-(prop-2-en-1-yloxy)propyl]-1H-1,2,3-triazol-4-yl}methyl)-
oxime (7k). Purified by CC (SiO2; AcOEt/hexane 1:1). Yield 0.63 g (81%). Colorless oil. Rf (AcOEt/
hexane 8 :1) 0.62. IR (film): 3400 (br.), 3080m, 2947m, 1660s, 1500m, 1456m, 1209s. 1H-NMR (CDCl3):
3.31 – 3.33 (m, OCH2CHOH); 3.85 – 3.87 (m, CH2CH ¼ C); 4.13 (s, OH, exchangeable with D2O); 4.23
(dd, J ¼ 6.7, 13.8, 1 H, NCH2); 4.38 (dd, J ¼ 3.6, 13.8, 1 H, NCH2); 4.75 – 4.77 (m, CHOH); 5.04 – 5.11 (m,
¼CH2); 5.20 (s, NOCH2); 5.71 – 5.82 (m, ¼CH); 7.20 – 7.42 (m, 10 arom. H); 7.70 (s, HꢀC(5) of triazole).
13C-NMR (CDCl3): 53.10; 67.62; 68.81; 71.18; 72.17; 117.24; 125.02; 127.96; 128.06; 128.23; 128.89; 129.24;
129.46; 132.98; 134.35; 136.20; 144.10; 157.45. MS: 392.18 (2.1, Mþ). Anal. calc. for C22H24N4O3 (392.45):
C 67.33, H 6.16, N 14.28; found: C 67.46, H 6.28, N 14.20.
Diphenylmethanone O-{[1-(3-Butoxy-2-hydroxypropyl)-1H-1,2,3-triazol-4-yl]methyl}oxime (7l).
Purified by CC (SiO2; AcOEt/hexane 1:1). Yield 0.71 g (87%). Yellow oil. Rf (AcOEt/hexane 8 :1)
0.57. IR (film): 3380 (br.), 3040s, 2956m, 1678m, 1505m, 1430m, 1242s. 1H-NMR (CDCl3): 0.87 (t, J ¼ 7.3,
Me); 1.32 – 1.38 (m, CH2 Me); 1.50 – 1.55 (m, OCH2CH2); 2.93 (s, OH, exchangeable with D2O); 3.33 –
3.46 (m, CH2OCH2); 4.14 – 4.18 (m, CHOH); 4.34 (dd, J ¼ 6.7, 14.0, 1 H, NCH2); 4.48 (dd, J ¼ 3.8, 13.9,
1 H, NCH2); 5.32 (s, NOCH2); 7.26 – 7.48 (m, 10 arom. H); 7.67 (s, HꢀC(5) of triazole). 13C-NMR
(CDCl3): 13.70; 18.72; 31.13; 52.84; 68.17; 68.71; 70.27; 72.03; 121.30; 125.60; 128.18; 128.49; 128.80;