(2H, m), 3.24–3.39 (2H, m), 3.4 (2H, t, J 8.4, CH2OH), 4.54 (2H,
d, J 5.6, HOCH2), 4.68 (1H, virtual q, J 8.4, 4-H), 4.71 (1H, t, J
5.3, D2O exch., OH), 5.13 (1H, virtual q, J 8.6, 3-H), 5.24 (1H,
t, J 5.7, D2O exch., OH), 7.42 (2H, d, J 8.2), 7.82 (2H, d, J 7.9)
ppm; 13C NMR (75.47 MHz, DMSO-d6) d 24.4 (CH), 33.9 (CH2),
39.5 (CH), 39.6 (CH2), 63.6 (CH2), 64.7 (CH2), 71.4 (CH), 126.9
(CH), 127.7 (CH), 129.2 (C), 142.4 (C), 148.8 (C), 149.7 (C) ppm;
m/z (EI 70 eV) 273 (12%), 272 (4), 207 (21), 146 (28), 135 (12),
117 (15), 116 (24), 97(22), 91 (22), 90 (14), 89 (20), 80 (56), 79 (93),
77 (22), 69(24), 67 (64), 65 (21), 58 (100), 57 (38), 55 (30), 53 (11);
C15H17I2N3O2 (525.1233): calcd. C, 34.31; H, 3.26; N, 8.00; found
C, 34.69; H, 3.57; N, 8.34%
m), 7.86 (1H, s, 5-Htriazole) ppm; 13C NMR (75.47 MHz, CDCl3) d
26.6 (CH), 33.6 (CH2), 39.2 (CH), 40.0 (CH2), 65.1 (CH2), 71.4
(CH), 112.2 (CH), 115.1 (CH), 116.1 (CH), 119.6 (CH), 129.8
(CH), 131.2 (C), 146.9 (C), 147.6 (C) ppm; m/z (EI 70 eV) 384 (M,
15%), 256 (16), 160 (16), 132 (44), 131 (100), 117 (38), 104 (26),
85(14), 80 (18), 79 (28), 77 (20), 71 (19), 69 (20), 67 (28), 57 (24);
HRMS m/z calcd for C14H17IN4O, 384.2154; found, 384.2172.
( )-{t-3-Iodo-c-4-[4-(3-thienyl)-1H-1,2,3-triazol-1-yl]-r-1-
cyclopentyl}methanol (30a) and ( )-{t-3-iodo-c-4-[5-iodo-4-
(3-thienyl)-1H-1,2,3-triazol-1-yl]-r-1-cyclopentyl}methanol (30b)
Method A: The non-void fractions eluted with hexane–EtOAc 5 :
1, 3 : 1, 2 : 1 and 1 : 1 afforded successively 30b (11%) and 30a
(57%). Method B: The non-void fractions eluting with hexane–
EtOAc 3 : 1, 2 : 1, and 1 : 1 afforded 30a (89%) as a yellowish
oil that presented identical spectroscopic features to that using
Method A.
( )-2-{1-[c-4-(Hydroxymethyl)-t-2-iodo-r-1-cyclopentyl]-1H-
1,2,3-triazol-4-yl}benzaldehyde (28a) and ( )-2-{1-[c-4-
(hydroxymethyl)-t-2-iodo-r-1-cyclopentyl]-5-iodo-1H-1,2,3-
triazol-4-yl}benzaldehyde (28b)
Method A: The non-void fractions eluted with hexane–EtOAc 2 : 1
and 3 : 2 afforded successively 28b (13%) and 28a (49%). Method
B: The non-void fractions eluted with hexane–EtOAc 1 : 1 and
2 : 3 afforded 28a (64%) as a yellow oil that presented identical
spectroscopic features to that using Method A.
30a: Yellowish oil; mmax/cm−1 3356, 3126, 2924, 2868, 1596, 1446,
1353, 1314, 1228, 1046, 856, 786, 622; 1H NMR (300 MHz, CDCl3)
d 1.85–2.06 (1H, m), 2.09–2.31 (3H, m), 2.34–2.51 (1H, m), 3.09
(1H, br s, D2O exch., OH), 3.53–3.55 (2H, m, HOCH2), 4.30 (1H,
virtual q, J 7.8, 3-H), 4.84 (1H, virtual q, J 8.1, 4-H), 7.21–7.09
(1H, m), 7.24–7.28 (1H, m), 7.49–7.51 (1H, m), 7.69 (1H, s, 5-
Htriazole) ppm; 13C NMR (75.47 MHz, CDCl3) d 26.4 (CH), 33.6
(CH2), 38.9 (CH), 39.8 (CH2), 64.7 (CH2), 71.2 (CH), 119.4 (CH),
121.3 (CH), 125.7 (CH), 126.4 (CH), 131.3 (C), 143.6 (C) ppm;
m/z (EI 70 eV) 375 (M, 43%), 220 (19), 207 (18), 202 (14), 162
(13), 123 (31), 122 (100), 108 (25), 97 (22), 80 (15), 79 (29), 67 (14);
HRMS m/z calcd for C12H14IN3OS, 375.2285; found, 375.2306.
30b: Yellowish solid, mp 95–97◦C; mmax/cm−1 3369, 2918, 1651,
28a: Yellow oil. mmax/cm−13353, 2929, 1688, 1602, 1445, 1198,
1
1044, 827, 769; H NMR (300 MHz, CDCl3) d 2.22–2.68 (6H,
m, one of them D2O exch., OH), 3.75–3.78 (2H, m, HOCH2),
4.53 (1H, virtual q, J 7.6, 2-H), 5.11 (1H, virtual q, J 7.9, 1-H),
7.48–7.53 (1H, m), 7.62–7.67 (1H, m), 7.71–7.73 (1H, m), 7.96–
8.02 (1H, m), 8.05 (1H, s, 5-Htriazole), 10.37 (1H, s, CHO) ppm; 13
C
NMR (75.47 MHz, CDCl3) d 26.5 (CH), 33.5 (CH2), 39.0 (CH),
40.0 (CH2), 65.0 (CH2), 71.5 (CH), 123.2 (CH), 128.7 (CH), 128.9
(CH), 130.1 (CH), 132.8 (C), 133.8 (CH), 144.4 (C), 192.5 (C) ppm;
m/z (EI 70 eV) 370 [(M + 2) − CHO, 16%], 369 [(M + 1) − CHO,
100], 207 (27), 146 (25), 145 (18), 128 (18), 102 (15), 89 (17), 79
(14), 59 (15); HRMS m/z calcd for C15H16IN3O2, 397.2109; found,
397.2134.
1
1585, 1429, 1148, 1030, 787; H NMR (300 MHz, CDCl3) d 2.0
(1H, br s, D2O exch., OH), 2.12–2.21 (2H, m), 2.34–2.53 (1H, m),
2.54–2.63 (1H, m), 2.66–2.79 (1H, m), 3.77–3.81 (2H, m, HOCH2),
4.69 (1H, virtual q, J 6.6, 3-H), 5.17 (1H, virtual q, J 7.2, 4-H),
7.41–7.44 (1H, m), 7.75–7.81 (1H, m), 7.97–7.98 (1H, m) ppm; 13
C
28b: Yellow solid, mp 73–74◦C; mmax/cm−1 3375, 2923, 1688,
1797, 1196, 1039, 823, 769; 1H NMR (300 MHz, CDCl3) d 2.06–
2.26 (2H, m, one of them D2O exch., OH), 2.28–2.46 (1H, m),
2.47–2.59 (1H, m), 2.62–2.75 (1H, m), 3.74–3.79 (2H, m, HOCH2),
4.70 (1H, virtual q, J 7.3, 2-H), 5.13 (1H, virtual q, J 7.5, 1-H),
7.56–7.59 (2H, m), 7.66–7.70 (1H, m), 8.06 (1H, d, J 8.4), 9.98
(1H, s, CHO) ppm; 13C NMR (75.47 MHz, CDCl3) d 25.7 (CH),
34.0 (CH2), 39.6 (CH), 39.7 (CH2), 65.3 (CH2), 71.5 (CH), 128.2
(CH), 129.6 (CH), 131.2 (CH), 132.8 (C), 133.7 (CH), 134.5 (C),
148.1 (C), 191.4 (C) ppm; m/z (ESI-TOF) 523.93 (M + 1, 100%);
C16H15I2N3O2 (522.9254): calcd. C, 34.44; H, 2.89; N, 8.03; found
C 34.68, H 3.10, N 8.34%.
NMR (75.47 MHz, CDCl3) d 25.9 (CH), 33.7 (CH2), 39.5 (CH2),
39.6 (CH), 65.2 (CH2), 70.9 (CH), 122.9 (CH), 125.9 (CH), 126.5
(CH), 130.6 (C), 146.3 (C), 146.4 (C) ppm; m/z (EI 70 eV) 501 (M,
33%), 346 (27), 248 (62), 247 (100), 218 (20), 207 (63), 123 (24),
122 (74), 121 (45), 97 (26), 95 (34), 94 (14), 80 (42), 79 (83), 67 (28);
C12H13I2N3OS (500.8869): calcd. C, 28.76; H, 2.61; N, 8.39; found
C, 29.08; H, 2.59; N, 8.54%.
( )-{t-3-Iodo-c-4-[4-(2-pyridinyl)-1H-1,2,3-triazol-1-yl]-r-1-
cyclopentyl}methanol (31a)
Method A: The non-void fractions eluted with hexane–EtOAc 1 :
1, 2 : 3, and 1 : 3 afforded 31a (29%). Method B: The non-void
fractions eluted with hexane–EtOAc 3 : 1, 2 : 1, and 1 : 1 afforded
31a (68%) as a white solid that presented identical spectroscopic
features to that using method A.
( )-{c-3-[4-(2-Aminophenyl)-1H-1,2,3-triazol-1-yl]-t-4-iodo-r-1-
cyclopentyl}methanol (29a)
Method B: The non-void fractions eluted with hexane–EtOAc 1 :
2 and 1 : 3 afforded 29a (75%).
31a: White solid, mp 151–152◦C (recrystallized from EtOAc);
mmax/cm−1 3150, 2931, 1600, 1466, 1243, 1134, 1040, 779; 1H NMR
(300 MHz, CDCl3) d 2.04–2.14 (1H, m, D2O exch., OH), 2.16–2.26
(1H, m), 2.32–2.69 (4H, m), 3.75 (2H, d, J 5.3, HOCH2), 4.55 (1H,
virtual q, J 7.6, 3-H), 5.12 (1H, virtual q, J 7.9, 4-H), 7.22–7.28
(1H, m), 7.76–7.81 (1H, m), 8.18 (1H, d, J 7.9), 8.29 (1H, s, 5-
Htriazole), 8.57–8.59 (1H, m) ppm; 13C NMR (75.47 MHz, CDCl3)
29a: Brownish oil; mmax/cm−1 3361, 2920, 1619, 1460, 1045, 908,
786, 729; 1H NMR (300 MHz, CDCl3) d 2.17–2.65 (6H, m, one of
them D2O exch., OH), 3.12 (2H, br s, D2O exch., NH2), 3.73–3.78
(2H, m, HOCH2), 4.50 (1H, virtual q, J 7.5, 4-H), 5.04 (1H, virtual
q, J 7.9, 3-H), 6.66 (1H, ddd, J 7.6, 2.3 and 1.7), 7.12–7.25 (3H,
This journal is
The Royal Society of Chemistry 2007
Org. Biomol. Chem., 2007, 5, 3805–3813 | 3811
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