A. H. Sandtorv, H.-R. Bjørsvik
FULL PAPER
29.3, 29.2, 29.0, 28.5, 22.8, 21.9, 19.5, 14.2 ppm. FTIR (neat): ν =
N-Tosyl-4-(3-methoxyprop-1-ynyl)imidazole (7l): [new compd.]. Iso-
lated as yellowish crystals in a yield of 16%. The product was un-
stable and degraded rapidly; m.p. 94.0–98.9 °C. Rf = 0.62 [EtOAc/
hexane (4:6)]. 1H NMR (CDCl3): δ = 7.92 (s, 1 H), 7.81 (d, J =
8.1 Hz, 2 H), 7.40 (s, 1 H), 7.36 (d, J = 8.5 Hz, 2 H), 4.27 (s, 2 H),
3.40 (s, 3 H), 2.45 (s, 3 H) ppm. 13C NMR (CDCl3): δ = 147.1,
136.7, 134.7, 130.8, 127.8, 126.6, 120.0, 87.3, 78.3, 60.4, 58.0,
˜
3143 (w), 3066 (w), 2916 (s), 2840 (w), 1594 (w), 1479 (w), 1373
(m), 1168 (s), 1090 (s), 819 (m), 684 (s), 600 (s), 574 (s) cm–1. MS
(EI) m/z (%) = 358.2 (4, MM+), 261.1 (12), 203.2 (34), 155.0 (31),
133.1 (19), 105.0 (16), 91.0 (100), 81.0 (21), 65.0 (27). HRMS
(DART): m/z calcd. for C20H27N2O2S [MH]+ 359.1793; found
359.1791.
22.0 ppm. FTIR (neat): ν = 3134 (w), 2930 (w), 2822 (w), 1594 (w),
˜
N-Tosyl-4-(2-cyclopentylethynyl)imidazole (7e): [new compd.]. Iso-
1476 (w), 1374 (m), 1266 (m), 1166 (s), 1085 (s), 1010 (m), 680 (s),
815 (m), 585 (s) cm–1. MS (EI) m/z (%) = 290.1 (MM+, 6), 259.1
(1), 155.0 (19), 91.0 (100), 65.0 (44). HRMS (DART): m/z calcd.
for C14H15N2O3S [MH]+ 291.0803; found 291.0806.
lated as pale yellow crystals in a yield of 93%; m.p. 97.7–103.0 °C.
1
Rf = 0.45 [EtOAc/hexane (4:6)]. H NMR (CDCl3): δ = 7.90 (s, 1
H), 7.80 (d, J = 9.2 Hz, 2 H), 7.35 (d, J = 8.6 Hz, 2 H), 7.30 (s, 1
H), 2.77 (m, 1 H), 2.44 (s, 3 H), 1.94 (m, 2 H), 1.68 (m, 6 H) ppm.
13C NMR (CDCl3): δ = 146.7, 136.3, 134.8, 130.7, 127.8, 127.6,
N-Tosyl-4-(3,3-diethoxyprop-1-ynyl)imidazole (7m): [new compd.].
Isolated as a dark brown oil in a yield of 59%. The compound was
119.4, 96.9, 71.8, 33.7, 30.7, 25.2, 21.9 ppm. FTIR (neat): ν = 3141
˜
1
unstable and degraded rapidly. Rf = 0.43 [EtOAc/hexane (3:7)]. H
(w), 2960 (w), 2868 (w), 1594 (w), 1479 (w), 1374 (s), 1167 (s), 1093
(s), 814 (m), 703 (m), 675 (s), 585 (s) cm–1. MS (EI) m/z (%) = 314.2
(16, MM+), 159.1 (22), 155.0 (27), 132.1 (22), 91.0 (100), 77.0 (14),
65.0 (29). HRMS (DART): m/z calcd. for C17H19N2O2S [MH]+
315.1167; found 315.1166.
NMR (CDCl3): δ = 7.92 (s, 1 H), 7.79 (d, J = 8.4 Hz, 2 H), 7.42
(s, 1 H), 7.35 (d, J = 8.3 Hz, 2 H), 5.40 (s, 1 H), 3.68 (m, 4 H),
2.43 (s, 3 H), 1.21 (t, J = 7.0 Hz, 6 H) ppm. 13C NMR (CDCl3): δ
= 147.0, 136.5, 134.5, 130.7, 127.6, 126.0, 121.4, 91.7, 86.5, 77.1,
61.3, 21.9, 15.2 ppm. FTIR (neat): ν = 3139 (w), 2975 (m), 2930
˜
N-Tosyl-4-(2-[4-tert-butylphenyl]ethynyl)imidazole
(7f):
[new
(w), 2242 (w), 1594 (m), 1482 (m), 1375 (s), 1332 (s), 1169 (s), 1081–
1006 (s, br.), 681 (s), 585 (s) cm–1. MS (EI) m/z (%) = 303.2 (12),
155.1 (35), 91.1 (100), 65.1 (36). HRMS (DART): m/z calcd. for
C17H21N2O4S [MH]+ 349.1217; found 349.1225.
compd.]. Isolated as pale crystals in a yield of 43%; m.p. 126.5–
1
132.3 °C. Rf = 0.58 [EtOAc/hexane (4:6)]. H NMR (CDCl3): δ =
7.99 (s, 1 H), 7.84 (d, J = 7.7 Hz, 2 H), 7.46 (s, 1 H), 7.42 (d, J =
6.6 Hz, 2 H), 7.37–7.33 (m, 6 H), 2.45 (s, 3 H), 1.30 (s, 9 H) ppm.
13C NMR (150 MHz, CDCl3): δ = 152.2, 146.9, 136.8, 134.6, 131.6,
130.8, 127.7, 127.4, 125.6, 120.2, 119.4, 91.6, 80.4, 35.0, 31.3,
N-Tosyl-4-(10-hydroxydec-1-ynyl)imidazole (7q): [new compd.] Iso-
lated as a white solid in a yield of 73% over two steps. Rf = 0.42
[EtOAc/hexane (1:1)]. 1H NMR (CDCl3): δ = 7.90 (s, 1 H), 7.80
(d, J = 8.4 Hz, 2 H), 7.35 (d, J = 8.3 Hz, 2 H), 7.31 (s, 1 H), 3.63
(t, J = 6.5 Hz, 2 H), 2.44 (s, 3 H), 2.36 (t, J = 7.0 Hz, 2 H), 1.55
(m, 4 H), 1.40 (m, 2 H), 1.31 (m, 7 H) ppm. 13C NMR (CDCl3): δ
= 146.7, 136.2, 134.7, 130.6, 127.6, 127.4, 119.5, 92.7, 72.4, 63.2,
32.9, 29.3, 29.0, 29.7, 28.3, 25.7, 21.8, 19.4 ppm. HRMS (DART):
m/z calcd. for C20H27N2O3S [MH]+ 375.17424; found 375.17444.
22.0 ppm. FTIR (neat): ν = 3105 (w), 2955 (w), 2923 (w), 1592 (w),
˜
1478 (w), 1378 (m), 1334 (m), 1169 (s), 1079 (s), 813 (m), 669 (s),
585 (s) cm–1. MS (EI) m/z (%) = 378.2 (32, MM+), 363.2 (36), 223.2
(23), 208.2 (38), 155.1 (24), 91.1 (100), 65.0 (47). HRMS (DART):
m/z calcd. for C22H23N2O2S [MH]+ 379.1480; found 379.1482.
N-Tosyl-4-(2-[4-pentyl]phenyl)ethynylimidazole (7g): [new compd.].
Isolated as pale crystals in a yield of 74%; m.p. 103.6–105.2 °C. Rf
N-Tosyl-4-(3-hydroxy-3,4,4-trimethylpent-1-ynyl)imidazole
(7r):
1
= 0.13 EtOAc/hexane (2.5:7.5). H NMR (CDCl3): δ = 7.97 (s, 1
[new compd.]. Isolated as pale crystals in a yield of 82%; m.p.
164.1–166.3 °C. Rf = 0.42 [EtOAc/hexane (4:6)]. 1H NMR (CDCl3):
δ = 7.94 (s, 1 H), 7.81 (d, J = 8.3 Hz, 2 H), 7.36 (m, 3 H), 2.43 (s,
3 H), 1.48 (s, 3 H), 1.04 (s, 9 H) ppm. 13C NMR (CDCl3): δ =
146.9, 136.4, 134.6, 130.7, 127.7, 126.8, 120.2, 95.1, 75.8, 74.4, 38.4,
H), 7.84 (d, J = 8.2 Hz, 2 H), 7.45 (s, 1 H), 7.39 (dd, J1 = 8.2, J2
= 6.1 Hz, 4 H), 7.13 (d, J = 8.1 Hz, 2 H), 2.59 (t, J n = 7.6 Hz, 2
H), 2.43 (s, 3 H), 1.59 (qv, J = 7.3 Hz, 2 H), 1.31 (m, J = 3.3 Hz,
4 H), 0.88 (t, J = 6.7 Hz, 3 H) ppm. 13C NMR (CDCl3): δ = 146.8,
144.1, 136.5, 134.6, 131.7, 130.7, 128.6, 127.7, 127.4, 120.1, 119.5,
25.3, 24.7, 21.8 ppm. FTIR (neat): ν = 3400–3150 (br., m), 3145
˜
91.4, 80.4, 36.0, 31.6, 31.0, 22.6, 21.9, 14.2 ppm. FTIR (neat): ν =
˜
(m), 3140 (m), 2956 (m), 1594 (m), 1483 (s), 1372 (s), 1329 (s), 1258
(w), 1174 (s), 1080 (s), 1005 (w), 848 (m), 812 (s), 670 (s) cm–1. MS
(EI) m/z (%) = 289.1 (20), 281.1 (3), 247.1 (14), 155.0 (36), 135.0
(37), 91.0 (100), 65.0 (24). HRMS (DART): m/z calcd. for
C18H23N2O3S [MH]+ 347.1429; found 347.1426.
3143 (w), 2917 (w), 1285 (w), 1594 (w), 1478 (m), 1373 (s), 1333
(m), 1165 (s), 1082 (s), 813 (m), 679 (s), 600 (s), 582 (s) cm–1. MS
(EI) m/z (%) = 392.2 (51, MM+), 335.2 (9), 237.2 (100), 183.2 (34),
155.0 (19), 126.1 (33), 91.0 (84), 65.0 (24). HRMS (DART): m/z
calcd. for C23H25N2O2S [MH]+ 393.1637; found 393.1635.
N-Tosyl-4-(2-[trimethylsilyl]ethyn-1-yl)imidazole (7s): [new compd.].
Isolated as dark brown crystals in a yield of 85%; m.p. 91.0–
95.0 °C. Rf = 0.67 [EtOAc/hexane (3:7)]. 1H NMR (CDCl3): δ =
7.90 (s, 1 H), 7.79 (d, J = 8.0 Hz, 2 H), 7.40 (s, 1 H), 7.33 (d, J =
8.8 Hz, 2 H), 2.41 (s, 3 H), 0.18 (s, 9 H) ppm. 13C NMR (CDCl3):
δ = 146.8, 136.1, 134.4, 130.5, 127.5, 127.0, 120.8, 97.2, 96.0, 21.8,
N-Tosyl-4-(3-hydroxyprop-1-ynyl)imidazole (7i): [new compd.]. Iso-
lated as a white solid in a yield of 91% over two steps. Rf = 0.59
[EtOAc/hexane (1:1)]. 1H NMR (CDCl3): δ = 7.93 (s, 1 H), 7.82
(d, J = 8.5 Hz, 2 H), 7.39 (d, J = 8.4 Hz), 7.36 (s, 1 H), 4.44 (br. s,
2 H), 2.46 (s, 3 H), 2.04 (br. s, 1 H) ppm. 13C NMR (CDCl3): δ =
147.0, 136.5, 134.5, 130.8, 127.8, 126.5, 120.7, 89.7, 51.6, 21.9 ppm.
HRMS (DART): m/z calcd. for C13H13N2O3S [MH]+ 277.06469;
found 277.06477.
0.18 ppm. FTIR (neat): ν = 3140 (w), 2959 (w), 2166 (m), 1592 (w),
˜
1479 (w), 1377 (m), 1326 (m), 1243 (m), 1171 (m), 1089 (m), 971
(m), 840 (s), 704 (m), 672 (s), 587 (s) cm–1. MS (EI) m/z (%) = 318.2
(70, MM+), 303.1 (80), 155.0 (73), 91.0 (100), 65.0 (74). HRMS
(DART): m/z calcd. for C15H19N2O2SSi [MH]+ 319.0937; found
319.0935.
N-Tosyl-4-(4-hydroxybut-1-ynyl)imidazole (7k): [new compd.]. Iso-
lated as a white solid in a yield of 81% over two steps. Rf = 0.43
1
[EtOAc]. H NMR (CDCl3): δ = 7.92 (s, 1 H), 7.81 (d, J = 7.2 Hz,
2 H), 7.36 (m, 3 H), 3.78 (br. s, 2 H), 2.65 (t, J = 6.2 Hz, 2 H), N-Tosyl-4-(3-methylbut-3-en-1-ynyl)imidazole (7t): [new compd.].
2.45 (s, 3 H), 2.20 (br. s, 1 H) ppm. 13C NMR (CDCl3): δ = 146.9,
The title compound was isolated as yellow crystals in a yield of
136.4, 134.7, 130.7, 127.7, 127.1, 120.0, 89.2, 74.2, 61.0, 24.0,
67%; m.p. 98.3–99.9 °C. Rf = 0.74 [EtOAc/hexane (1:1)]. 1H NMR
22.0 ppm. HRMS (DART): m/z calcd. for C14H15N2O3S [MH]+ (CDCl3): δ = 7.93 (s, 1 H), 7.80 (d, J = 8.3 Hz, 2 H), 7.39 (s, 1 H),
291.08034; found 191.08066.
7.35 (d, J = 8.0 Hz, 2 H), 5.37 (s, 1 H), 5.29 (s, 1 H), 2.42 (s, 3 H),
4664
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Eur. J. Org. Chem. 2015, 4658–4666