Job/Unit: O43583
/KAP1
Date: 22-01-15 14:50:32
Pages: 10
J. Zhu, Y. Kong, F. Lin, B. Wang, Z. Chen, L. Liu
FULL PAPER
249.09070 (100%), 251.08775 (32%); found 249.09010 (100%), (t, J = 7.8 Hz, 1 H, Ar-H), 7.76 (d, J = 7.8 Hz, 1 H, Ar-H), 7.79
251.08696 (32%).
(s, 1 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 21.5, 48.4,
66.3, 115.0, 118.4, 121.7, 127.1, 129.0, 139.2, 139.9, 157.3 ppm. IR
2-(4-Chlorophenyl)-4-(pyrrolidin-1-yl)-2H-1,2,3-triazole (4f): Color-
less liquid. 1H NMR (400 MHz, CDCl3): δ = 2.01 (dt, J = 3.3,
6.6 Hz, 4 H, 2ϫCH2), 3.39 (dt, J = 3.3, 6.6 Hz, 4 H, 2ϫCH2),
7.13 (s, 1 H, Ar-H), 7.38 (dt, J = 2.9, 8.9 Hz, 2 H, Ar-H), 7.89 (dt,
J = 2.9, 8.9 Hz, 2 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ
= 25.4, 48.5, 118.6, 121.7, 129.1, 130.9, 138.7, 155.5 ppm. IR
(KBr): νmax = 1578, 1556, 1452, 1267, 1133, 918, 787 cm–1. HRMS
˜
(ESI): calcd. for C13H17N4O [M + H]+ 245.14024; found 245.13957
(100%).
4-[2-(4-Methoxyphenyl)-2H-1,2,3-triazol-4-yl]morpholine (4m): Col-
orless liquid. 1H NMR (400 MHz, CDCl3): δ = 3.29 (t, J = 4.8 Hz,
4 H, 2 ϫ CH2), 3.85 (s, 3 H, OCH3), 3.88 (t, J = 4.8 Hz, 4 H,
2ϫCH2), 6.96 (dt, J = 2.2, 7.0 Hz, 2 H, Ar-H), 7.22 (s, 1 H, Ar-
H), 7.86 (dt, J = 2.2, 7.0 Hz, 2 H, Ar-H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 48.5, 55.6, 66.3, 114.2, 119.3, 121.2, 133.9,
(KBr): νmax = 1539, 1493, 1088, 941, 824 cm–1. HRMS (ESI): calcd.
˜
for C12H14ClN4 [M + H]+ 249.09070 (100%), 251.08775 (32%);
found 249.09000 (100%), 251.08696 (32%).
2-(4-Fluorophenyl)-4-(pyrrolidin-1-yl)-2H-1,2,3-triazole (4g): Color-
less liquid. 1H NMR (400 MHz, CDCl3): δ = 2.01 (dt, J = 3.3,
6.6 Hz, 4 H, 2ϫCH2), 3.38 (dt, J = 3.3, 6.6 Hz, 4 H, 2ϫCH2),
7.10 (s, 1 H, Ar-H), 7.12 (dt, J = 2.2, 9.2 Hz, 2 H, Ar-H), 7.92 (dt,
J = 2.2, 9.2 Hz, 2 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ
= 25.4, 48.5, 115.7 (d, J = 23.0 Hz), 119.1 (d, J = 8.1 Hz), 136.6,
157.3, 158.1 ppm. IR (KBr): ν
= 1550, 1510, 1251, 1113,
˜
max
834 cm–1. HRMS (ESI): calcd. for C13H17N4O [M + H]+
261.13515; found 261.13465 (100%).
4-[2-(4-Fluorophenyl)-2H-1,2,3-triazol-4-yl]morpholine (4n): Color-
1
less liquid. H NMR (400 MHz, CDCl3): δ = 3.30 (t, J = 4.8 Hz,
155.5, 160.7 (d, J = 244.5 Hz) ppm. IR (KBr): ν
= 1595, 1508,
˜
4 H, 2ϫCH2), 3.87 (t, J = 4.8 Hz, 4 H, 2ϫCH2), 7.13 (dt, J = 2.2,
9.1 Hz, 2 H, Ar-H), 7.25 (s, 1 H, Ar-H), 7.92 (dt, J = 2.2, 9.1 Hz,
2 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 48.3, 66.3,
115.9 (d, J = 23.2 Hz), 116.2 (d, J = 8.1 Hz), 121.9, 136.3 (d, J =
max
1210, 943, 831, 628 cm–1. HRMS (ESI): calcd. for C12H14FN4 [M
+ H]+ 233.12025; found 233.11968 (100%).
4-(Pyrrolidin-1-yl)-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
1
2.6 Hz), 157.5, 161.0 (d, J = 245.5 Hz) ppm. IR (KBr): νmax = 1548,
˜
(4h): Colorless liquid. H NMR (400 MHz, CDCl3): δ = 2.03 (dt,
1508, 1444, 1213, 1112, 835 cm–1. MS-EI: m/z (%) = 95 (25), 109
(17), 190 (84), 217 (6), 233 (8), 248 (100). C12H13FN4O (248.26):
calcd. C 58.06, H 5.28, N 22.57; found C 57.78, H 5.51, N 22.29.
J = 3.3, 6.7 Hz, 4 H, 2ϫCH2), 3.41 (dt, J = 3.3, 6.7 Hz, 4 H,
2ϫCH2), 7.18 (s, 1 H, Ar-H), 7.67 (d, J = 8.5 Hz, 2 H, Ar-H), 8.05
(d, J = 8.5 Hz, 2 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ
= 25.4, 48.4, 117.2, 122.7, 124.4 (d, J = 271.7 Hz), 126.3 (q, J =
4-{2-[4-(Trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl}morpholine
(4o): Waxy solid. 1H NMR (400 MHz, CDCl3): δ = 3.33 (t, J =
4.8 Hz, 4 H, 2ϫCH2), 3.88 (t, J = 4.8 Hz, 4 H, 2ϫCH2), 7.32 (s,
1 H, Ar-H), 7.69 (d, J = 8.6 Hz, 2 H, Ar-H), 8.06 (d, J = 8.6 Hz,
2 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 48.1, 66.2,
117.5, 123.1, 124.0 (d, J = 271.7 Hz), 126.4 (q, J = 3.6 Hz), 127.8
3.7 Hz), 127.2 (d, J = 32.8 Hz), 142.3, 115.6 ppm. IR (KBr): ν
˜
max
= 1584, 1325, 1162, 1114, 1065, 932, 839 cm–1. MS-EI: m/z (%) =
70 (12), 145 (28), 213 (5), 226 (15), 254 (12), 263 (13), 282 (100).
C13H13F3N4 (282.2693): calcd. C 55.32, H 4.64, N 19.85; found C
55.17, H 4.93, N 19.62.
(d, J = 33.0 Hz), 142.1, 157.8 ppm. IR (KBr): ν
= 1616, 1550,
˜
max
4-(2-Phenyl-2H-1,2,3-triazol-4-yl)morpholine (4i): Colorless liquid.
1H NMR (400 MHz, CDCl3): δ = 3.31 (t, J = 4.8 Hz, 4 H,
2ϫCH2), 3.87 (t, J = 4.8 Hz, 4 H, 2ϫCH2), 7.24–7.29 (m, 2 H,
Ar-H), 7.44 (dt, J = 2.0, 8.8 Hz, 2 H, Ar-H), 7.95 (dt, J = 2.0,
8.8 Hz, 2 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 48.4,
1359, 1171, 1110, 1062, 842 cm–1. HRMS (ESI): calcd. for
C13H14F3N4O [M + H]+ 299.11197; found 299.11123 (100%).
2-Methyl-1-(2-phenyl-2H-1,2,3-triazol-4-yl)piperidine (4p): Color-
1
less liquid. H NMR (400 MHz, CDCl3): δ = 1.17 (d, J = 6.7 Hz,
66.3, 117.8, 121.9, 126.2, 129.1, 140.0, 157.4 ppm. IR (KBr): ν
˜
max
3 H, CH3), 1.62–1.78 (m, 5 H), 1.84–1.93 (m, 1 H), 3.08 (dt, J =
13.3, 3.7 Hz, 1 H), 3.55 (dt, J = 13.4, 3.7 Hz, 1 H), 4.02–4.09 (m,
1 H), 7.21–7.25 (m, 2 H, Ar-H), 7.43 (dt, J = 2.0, 8.8 Hz, 2 H, Ar-
H), 7.95 (dt, J = 2.0, 8.8 Hz, 2 H, Ar-H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 13.1, 19.0, 25.2, 30.3, 42.8, 50.0, 117.6,
= 1595, 1560, 1497, 1264, 1177, 913, 756 cm–1. HRMS (ESI): calcd.
for C12H15N4O [M + H]+ 231.12459; found 231.12380 (100%).
4-[2-(3-Chlorophenyl)-2H-1,2,3-triazol-4-yl]morpholine (4j): Color-
1
less liquid. H NMR (400 MHz, CDCl3): δ = 3.31 (t, J = 4.8 Hz,
122.4, 125.7, 129.0, 140.2, 157.0 ppm. IR (KBr): νmax = 1556, 1500,
˜
4 H, 2ϫCH2), 3.87 (t, J = 4.8 Hz, 4 H, 2ϫCH2), 7.22 (dt, J = 2.0,
8.0 Hz, 1 H, Ar-H), 7.28 (s, 1 H, Ar-H), 7.36 (t, J = 8.0 Hz, 1 H,
Ar-H),7.84 (dt, J = 2.0, 8.0 Hz, 1 H, Ar-H), 7.97 (t, J = 2.0 Hz, 1
H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 48.2, 66.2, 115.7,
1129, 952 cm–1. HRMS (ESI): calcd. for C14H19N4 [M + H]+
243.16097; found 243.16052 (100%).
1-[2-(3-Chlorophenyl)-2H-1,2,3-triazol-4-yl]-2-methylpiperidine (4q):
Colorless liquid. 1H NMR (400 MHz, CDCl3): δ = 1.16 (d, J =
5.8 Hz, 3 H, CH3), 1.57–1.69 (m, 4 H), 1.72–1.79 (m, 1 H), 1.82–
1.92 (m, 1 H), 3.05 (dt, J = 13.2, 4.1 Hz, 1 H), 3.55 (dt, J = 13.2,
4.1 Hz, 1 H), 4.01–4.10 (m, 1 H), 7.18 (ddd, J = 8.1, 2.0, 1.0 Hz, 1
H, Ar-H), 7.22 (s, 1 H, Ar-H), 7.33 (t, J = 8.1 Hz, 1 H, Ar-H), 7.83
(ddd, J = 8.1, 2.0, 1.0 Hz, 1 H, Ar-H), 7.97 (t, J = 2.0 Hz, 1 H)
ppm. 13C NMR (100 MHz, CDCl3): δ = 13.2, 18.8, 25.2, 30.2, 42.6,
49.9, 115.5, 117.7, 123.0, 125.5, 130.1, 134.9, 141.0, 157.1 ppm. IR
118.0, 122.6, 126.1, 130.2, 135.0, 140.7, 157.5 ppm. IR (KBr): ν
˜
max
= 1592, 1542, 1484, 1446, 1117, 779 cm–1. MS-EI: m/z (%) = 111
(22), 171 (2), 206 (80), 220 (4), 264 (100). C12H13ClN4O (264.71):
calcd. C 54.45, H 4.95, N 21.17; found C 54.18, H 5.09, N 20.89.
4-[2-(o-Tolyl)-2H-1,2,3-triazol-4-yl]morpholine (4k): Colorless li-
quid. 1H NMR (400 MHz, CDCl3): δ = 2.42 (s, 3 H, CH3), 3.29 (t,
J = 4.8 Hz, 4 H, 2ϫCH2), 3.88 (t, J = 4.8 Hz, 4 H, 2ϫCH2), 7.26–
7.32 (m, 4 H, Ar-H), 7.52–7.56 (m, 1 H, Ar-H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 19.2, 48.5, 66.3, 121.2, 124.7, 126.5, 128.0,
(KBr): νmax = 1592, 1550, 1485, 1449, 951, 777 cm–1. HRMS (ESI):
˜
calcd. for C14H18ClN4 [M + H]+ 277.12200 (100 %), 279.11905
(32%); found 277.12135 (100%), 279.11843 (32%).
131.7, 132.3, 139.7, 157.1 ppm. IR (KBr): νmax = 1549, 1497, 1455,
˜
1268, 1119, 762 cm–1. HRMS (ESI) calcd. for C13H17N4O
[M+ H]+ 245.14024; found 245.13967 (100%).
2-Methyl-1-[2-(m-tolyl)-2H-1,2,3-triazol-4-yl]piperidine (4r): Color-
1
4-[2-(m-Tolyl)-2H-1,2,3-triazol-4-yl]morpholine (4l): Colorless li-
less liquid. H NMR (400 MHz, CDCl3): δ = 1.16 (d, J = 6.7 Hz,
quid. 1H NMR (400 MHz, CDCl3): δ = 2.43 (s, 3 H, CH3), 3.31 3 H, CH3), 1.58–1.69 (m, 4 H), 1.72–1.78 (m, 1 H), 1.85–1.93 (m,
(dt, J = 3.4, 4.8 Hz, 4 H, 2ϫCH2), 3.87 (dt, J = 3.4, 4.8 Hz, 4 H,
2ϫCH2), 7.08 (d, J = 7.8 Hz, 1 H, Ar-H), 7.26 (s, 1 H, Ar-H), 7.32
1 H), 2.42 (s, 3 H, CH3), 3.08 (dt, J = 13.3, 4.0 Hz, 1 H), 3.57 (dt,
J = 13.3, 4.0 Hz, 1 H), 4.01–4.08 (m, 1 H), 7.06 (d, J = 7.8 Hz, 1
6
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