Hashem Sharghi et al.
FULL PAPERS
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J2 =3.9 Hz), 4.36 (dd, 1H, J1 =12.3, J2 =8.4 Hz), 4.94 (s,
2H), 5.44 (dd, 1H, J1 =8.2, J2 =3.9 Hz), 6.72–6.76 (m, 3H),
6.99–7.16 (m, 7H), 7.40 (s, 1H); 13C NMR (CDCl3,
62.9 MHz): d=61.9, 64.2, 65.8, 114.8, 116.2, 121.4, 123.9,
127.6, 128.8, 129.0, 130.1, 136.2, 143.6, 158.0; MS: m/z (%)=
297 (M+ +2, 1.0), 296 (M+ +1, 3.2), 295 (M+, 10.6), 236
(4.5), 202 (42.3), 174 (23.4), 144 (48.0), 121 (100.0) base
peak, 103 (84.6), 77 (75.9), 54 (73.2); anal. calcd. for
C17H17N3O2 (295.34): C 69.14, H 5.80, N 14.23%; found: C
69.17, H 5.82, N 14.21%.
(w), 3059 (w), 3418 (br) cmÀ1; H NMR (CDCl3, 250 MHz):
d=2.81 (s, 1H), 4.13 (dd, 1H, J1 =12.4, J2 =3.8 Hz), 4.49
(dd, 1H, J1 =12.4, J2 =8.4 Hz), 5.20 (s, 2H), 5.54 (dd, 1H,
J1 =8.2, J2 =3.7 Hz), 6.74 (d, 2H, J=8.0 Hz), 6.88 (t, 2H, J=
7.4 Hz), 6.99–7.10 (m, 5H), 7.09 (dd, 2H, J1 =7.5, J2 =
1.5 Hz), 7.28 (dd, 2H, J1 =5.4, J2 =1.7 Hz), 7.29 (s, 1H);
13C NMR (CDCl3, 62.9 MHz): d=44.9, 64.9, 67.1, 115.3,
122.8, 123.5, 124.0, 126.7, 127.2, 128.8, 128.9, 136.0, 144.2,
144.9; MS: m/z (%)=402 (M+ +2, 0.7), 401 (M+ +1, 6.0),
400 (M+, 13.1), 280 (1.1), 236 (8.5), 198 (100.0) base peak,
121 (14.5), 103 (17.9), 83 (29.1), 55 (55.4); anal. calcd. for
C23H20N4OS (400.50): C 68.98, H 5.03, N 13.99%; found: C
68.96, H 5.05, N 13.97%.
1-Phenyl-2-[4-(p-tolyloxymethyl)-1H-1,2,3-triazol-1-yl]-
ethanol (3c): Colourless solid; yield: 86%; mp 94–958C. IR
(KBr): n=517 (m), 705 (s), 822 (s), 957 (m), 860 (m), 1007
(s), 1176 (m), 1234 (s), 1292 (w), 1458 (m), 1508 (s), 1608
2-[4-(Hydroxymethyl)-1H-1,2,3-triazol-1-yl]-1-phenyletha-
nol (3g): Colourless solid; yield: 86%; mp 110–1118C. IR
(KBr): n=702 (s), 795 (m), 849 (m), 1011 (s), 1084 (s), 1119
(s), 1234 (m), 1454 (s), 2893 (w), 2932 (w), 3167 (s), 3340
1
(w), 2870 (w), 3418 (br) cmÀ1; H NMR (CDCl3, 250 MHz):
d=2.15 (s, 3H), 4.04 (dd, 1H, J1 =12.1, J2 =4.0 Hz), 4.39
(dd, 1H, J1 =11.9, J2 =8.4 Hz), 4.95 (s, 2H), 5.55 (dd, 1H,
J1 =8.2, J2 =3.8 Hz), 6.71 (d, 2H, J=8.5 Hz), 6.93 (d, 2H,
J=8.3 Hz), 7.08–7.21 (m, 5H), 7.53 (s, 1H); 13C NMR
(CDCl3, 62.9 MHz): d=20.5, 61.9, 64.5, 67.2, 114.7, 123.7,
125.9, 128.8, 130.0, 130.5, 136.1, 143.9, 156.1; MS: m/z (%)=
311 (M+ +2, 1.2), 310 (M+ +1, 3.2), 309 (M+, 10.8), 250
(4.2), 202 (23.4), 174 (42.3), 144 (42.4), 121 (100.0) base
peak, 103 (80.7), 77 (73.9), 54 (88.5); anal. calcd. for
C18H19N3O2 (309.15): C 69.88, H 6.19, N 13.58%; found: C
69.86, H 6.16, N 13.56%.
(br) cmÀ1 1H NMR (CDCl3, 250 MHz): d=4.03 (dd, 1H,
;
J1 =12.3, J2 =3.6 Hz), 4.33–4.46 (m, 3H), 4.52 (s, 2H), 5.58
(dd, 1H, J1 =8.8, J2 =3.8 Hz), 7.13–7.30 (m, 5H), 7.52 (s,
1H); 13C NMR (CDCl3, 62.9 MHz): d=53.1, 64.5, 67.1,
122.9, 125.9, 127.1, 128.9, 136.0, 147.3; anal. calcd. for
C11H13N3O2 (219.240): C 60.26, H 5.98, N 19.17%; found: C
60.22, H 6.04, N 19.22%.
2-[1-(2-Hydroxy-2-phenylethyl)-1H-1,2,3-triazol-4-yl]pro-
pan-2-ol (3h): Colourless solid; yield: 82%; mp 119.5–
120.58C. IR (KBr): n=698 (m), 721 (m), 860 (m), 957 (m),
1076 (s), 1165 (s), 1358 (w), 1458 (w), 2970 (m), 3128 (m),
2-{4-[(4-Chlorophenoxy)methyl]-1H-1,2,3-triazol-1-yl}-1-
phenylethanol (3d): Colourless solid; yield: 89%; mp 83–
848C. IR (KBr): n=698 (m), 748 (w), 829 (m), 1053 (s),
1250 (s), 1493 (s), 1593 (w), 1716 (w), 2854 (w), 2928 (w),
3356 (br) cmÀ1 1H NMR (CDCl3, 250 MHz): d=1.53 (s,
;
6H), 2.99 (s, 2H), 4.09 (dd, 1H, J1 =12.7, J2 =3.7 Hz), 4.50
(dd, 1H, J1 =12.3, J2 =8.4 Hz), 5.54 (dd, 1H, J1 =8.3, J2 =
3.6 Hz), 7.15–7.31 (m, 5H), 7.43 (s, 1H); 13C NMR (CDCl3,
62.9 MHz): d=30.1, 64.7, 67.2, 68.2, 120.3, 127.2, 128.9,
136.1, 155.2; MS: m/z (%)=247 (M+, 0.8), 246 (3.3), 232
(36.8), 216 (20.8), 188 (28.7), 170 (41.3), 149 (14.2), 130
(42.5), 103 (100.0) base peak, 84 (70.7), 55 (47.8); anal.
calcd. for C13H17N3O2 (247.293): C 63.14, H 6.93, N 16.99%;
found: C 63.09, H 6.98, N 16.90%.
3105 (br) cmÀ1 1H NMR (CDCl3, 250 MHz): d=3.94 (dd,
;
1H, J1 =12.1, J2 =4.2 Hz), 4.28 (dd, 1H, J1 =12.1, J2 =
8.4 Hz), 4.32 (s, 1H), 4.83 (s, 2H), 5.47 (dd, 1H, J1 =8.3, J2 =
4.1 Hz), 6.62 (dd, 2H, J1 =6.9, J2 =2.1 Hz), 6.96 (dd, 2H,
J1 =6.8, J2 =2.2 Hz), 6.99–7.10 (m, 5H), 7.48 (s, 1H);
13C NMR (CDCl3, 62.9 MHz): d=61.9, 64.2, 67.4, 116.1,
123.9, 126.0, 127.3, 128.8, 128.9, 129.4, 129.6, 129.9, 136.1,
143.2, 156.8; MS: m/z (%)=331 (M+ +2, 0.3), 330 (M+ +1,
0.7), 329 (M+, 1.4), 271 (0.3), 270 (1.1), 209 (1.1), 210 (0.6),
144 (22.0), 121 (37.6), 103 (42), 83 (100.0) base peak, 54
(44.4); anal. calcd. for C17H16ClN3O2 (329.78): C 61.91, H
4.89, N 12.74%; found: C 61.90, H 4.87, N 12.72%.
2-(4-Butyl-1H-1,2,3-triazol-1-yl)-1-phenylethanol (3i): Oily
compound; yield: 80%. IR (neat): n=702 (s), 756 (m), 1072
(m), 1229 (m), 1454 (s), 1551 (w), 2932 (m), 3093 (m), 3302
(br) cmÀ1; H NMR (CDCl3, 250 MHz): d=0.89 (t, 3H, J=
1
2-{4-[(4-Nitrophenoxy)methyl]-1H-1,2,3-triazol-1-yl}-1-
phenylethanol (3e): Brown solid; yield: 88%; mp 108–
1098C. IR (KBr): n=690 (s), 752 (s), 841 (s), 868 (s), 1003
(s), 1061 (m), 1111 (s), 1176 (w), 1254 (s), 1384 (s), 1504 (s),
7.3 Hz), 1.24–1.41 (m, 2H), 1.53–1.65 (m, 2H), 2.65 (t, 2H,
J=7.5 Hz), 3.73 (s, 1H), 4.15 (dd, 1H, J1 =12.3, J2 =3.9 Hz),
4.53 (dd, 1H, J1 =12.3, J2 =8.4 Hz), 5.60 (dd, 1H, J1 =8.2,
J2 =3.8 Hz), 7.18–7.37 (m, 6H); 13C NMR (CDCl3,
62.9 MHz): d=13.8, 22.3, 25.1, 31.3, 64.7, 68.1, 121.5, 127.6,
128.6 128.8, 136.5, 148.1; anal. calcd. for C14H19N3O
(245.320): C 68.54, H 7.81, N 17.13%; found: C 68.44, H
7.69, N 17.08%.
7-{[1-(2-Hydroxy-2-phenylethyl)-1H-1,2,3-triazol-4-yl]-
methyl}-5,6,7,8,9,10-hexahydro-2H-1,13,4,7,10-benzodioxa-
triazacyclopentadecine-3,11ACTHNUGRTNEUNG(4H,12H)-dione (3j): Yellow
powder; yield: 84% yield; mp 05–1068C. IR (KBr): n=756
(m), 1053 (m), 1126 (m), 1219 (w), 1257 (s), 1439 (w), 1504
1593 (s), 2835 (w), 3151 (w), 3333 (br) cmÀ1 1H NMR
;
(CDCl3, 250 MHz): d=3.62 (s, 1H), 4.19 (dd, 1H, J1 =12.2,
J2 =3.9 Hz), 4.56 (dd, 1H, J1 =12.2, J2 =8.4 Hz), 5.24 (s,
2H), 5.68 (dd, 1H, J1 =8.2, J2 =3.8 Hz), 7.02 (d, 2H, J=
9.2 Hz), 7.21–7.35 (m, 5H), 7.69 (s, 1H), 8.15 (d, 2H, J=
9.2 Hz); 13C NMR (CDCl3, 62.9 MHz): d=62.3, 64.7, 67.3,
114.8, 124.0, 125.9, 127.1, 129.1, 129.2, 135.7, 141.8, 142.6,
163.1; MS: m/z (%)=310 (2.4), 281 (2.3), 228 (2.6), 202
(55.9), 156 (31.5), 144 (92.9), 129 (48.5), 121 (100.0) base
peak, 103 (78.9), 91 (54.6), 77 (39.9), 54 (32.5); anal. calcd.
for C17H16N4O4 (340.33): C 59.99, H 4.74, N 16.46%; found:
C 59.97, H 4.72, N 16.45%.
(s), 1535 (s), 1682 (vs), 2854 (w), 2932 (w), 3398 (s) cmÀ1
;
1H NMR (CDCl3, 250 MHz): d=2.77 (t, 4H, J=5.3 Hz),
3.48 (t, 4H, J=5.3 Hz), 3.77 (s, 2H), 4.07 (dd, 1H, J1 =12.3,
J2 =3.9 Hz), 4.36 (s, 4H), 4.44 (dd, 1H, J1 =12.3, J2 =
8.5 Hz), 4.50 (s, 1H), 5.54 (dd, 1H, J1 =8.3, J2 =3.8 Hz),
6.81–7.01 (m, 4H), 7.08–7.11 (m, 2H), 7.26–7.29 (m, 3H),
7.49 (s, 1H), 7.59 (s, 2H); 13C NMR (CDCl3, 62.9 MHz): d=
2-{4-[(10H-Phenothiazin-10-yl)methyl]-1H-1,2,3-triazol-1-
yl}-1-phenylethanol (3f): Colourless solid; yield: 78%; mp
151–1528C. IR (KBr): n=702 (m), 748 (s), 1053 (m), 1130
(m), 1223 (m), 1284 (w), 1335 (m), 1458 (s), 1589 (w), 2870
2406
ꢀ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2009, 351, 2391 – 2410