Facile Construction of Fused Triazoles
Compound 29: Yield 0.117 g (75%); m.p. 106–108 °C. IR (KBr): ν Compound 35: Yield 0.105 g (68%); m.p. 157–159 °C. IR (KBr): ν
˜
˜
= 2934, 2852, 1734, 1601, 1574, 1435, 1235, 1101, 912, 766 cm–1.
= 3065, 2919, 1555, 1514, 1439, 1221, 1101, 999, 826, 772 cm–1. 1H
1H NMR (400 MHz, CDCl3): δ = 7.30–7.35 (m, 6 H, Ar-H), 7.19 NMR (400 MHz, CDCl3): δ = 7.33–7.35 (m, 1 H, Ar-H), 7.19–7.25
(s, 1 H, Ar-H), 7.06 (br., 1 H, Ar-H), 5.73 (s, 2 H, NCH2), 4.56 (m, 3 H, Ar-H), 6.93–6.97 (m, 1 H, Ar-H), 6.89 (dd, J = 6.8, 2.4 Hz,
and 5.21 (2s, 4 H, 2 OCH2) ppm. 13C NMR (100 MHz, CDCl3): δ =
145.1, 139.6, 137.6, 135.2, 132.5, 130.5, 129.9, 129.1, 128.64, 128.58,
126.8, 126.7, 125.7, 124.7, 70.9, 67.5, 52.0 ppm. LC–MS: m/z = 312
[M]+. C17H14ClN3O (311.77): calcd. C 65.49, H 4.53, N 13.48;
found C 65.56, H 4.47, N 13.36.
2 H, Ar-H), 6.78 (dd, J = 7.6, 1.6 Hz, 1 H, Ar-H), 4.31 (br. s, 2 H,
OCH2), 3.83 (s, 3 H, OCH3), 3.08 (br. s, 2 H, CH2), 1.91–1.96 (m,
2 H, CH2) ppm. 13C NMR (100 MHz, CDCl3): δ = 159.9, 157.4,
146.0, 131.0, 130.4, 130.2, 130.0, 126.6, 124.0, 123.4, 121.9, 114.4,
76.8, 55.6, 25.4, 25.3 ppm. LC–MS: m/z = 308 [M + 1]+.
C18H17N3O2 (307.35): calcd. C 70.34, H 5.58, N 13.67; found C
70.19, H 5.49, N 13.81.
Compound 30: Yield 0.099 g (75%); m.p. 164–166 °C. IR (KBr): ν
˜
= 2928, 2845, 1593, 1501, 1451, 1235, 1113, 1090, 995, 924, 760
cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.51–7.53 (m, 3 H, Ar-H),
7.40–7.42 (m, 2 H, Ar-H), 7.28–7.36 (m, 2 H, Ar-H), 7.11 (t, J =
7.6 Hz, 1 H, Ar-H), 6.90 (d, J = 7.6 Hz, 1 H, Ar-H), 4.72 and 5.28
(2s, 4 H, 2 OCH2) ppm. 13C NMR (100 MHz, CDCl3): δ = 144.9,
139.3, 137.3, 131.8, 129.8, 129.7, 129.5, 128.8, 128.3, 128.0, 126.0,
125.5, 71.5, 67.8 ppm. LC–MS: m/z = 264 [M + 1]+. C16H13N3O
(263.30): calcd. C 72.99, H 4.98, N 15.96; found C 73.12, H 4.92,
N 16.07.
Compound 36: Yield 0.096 g (66%); m.p. 176–178 °C. IR (KBr): ν
˜
= 3057, 2920, 1514, 1435, 1221, 1101, 999, 826, 772 cm–1. 1H NMR
(400 MHz, CDCl3): δ = 7.32–7.36 (m, 1 H, Ar-H), 7.18–7.21 (m, 5
H, Ar-H), 6.94 (t, J = 7.6 Hz, 1 H, Ar-H), 6.76 (dd, J ≈ 7.6, 1.6 Hz,
1 H, Ar-H), 4.31 (br., 2 H, OCH2), 3.07 (br., 2 H, CH2), 2.37 (s, 3
H, CH3), 1.91–1.95 (m, 2 H, CH2) ppm. 13C NMR (100 MHz,
CDCl3): δ = 157.3, 146.0, 139.0, 134.4, 131.0, 130.3, 130.2, 129.8,
125.0, 123.9, 123.3, 121.9, 76.8, 25.4, 25.3, 21.2 ppm. LC–MS: m/z
= 292 [M + 1]+. C18H17N3O (291.35): calcd. C 74.21, H 5.88, N
14.42; found C 74.35, H 5.82, N 14.31.
Compound 31: Yield 0.112 g (77%); m.p. 160–162 °C. IR (KBr): ν
˜
= 2917, 2855, 1607, 1514, 1451, 1300, 1258, 1115, 1090, 993, 835,
765 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.25–7.34 (m, 4 H, Ar-
H), 7.12 (t, J ≈ 7.6 Hz, 1 H, Ar-H), 6.99–7.02 (m, 2 H, Ar-H), 6.94
(d, J = 8.0 Hz, 1 H, Ar-H), 4.70 and 5.26 (2s, 4 H, 2 OCH2), 3.86
(s, 3 H, OCH3) ppm. 13C NMR (100 MHz, CDCl3): δ = 160.4,
144.7, 139.3, 131.7, 130.2, 129.5, 128.6, 128.0, 127.9, 127.3, 125.6,
114.8, 71.5, 67.8, 55.6 ppm. LC–MS: m/z = 294 [M + 1]+.
C17H15N3O2 (293.32): calcd. C 69.61, H 5.15, N 14.33; found C
69.55, H 5.21, N 14.28. This compound was crystallized from a
dichloromethane/hexane (2:1) mixture at 25 °C and its X-ray struc-
ture was determined.
Compound 37: Yield 0.110 g (62%); m.p. 156–158 °C. IR (KBr): ν
˜
= 3090, 2922, 1497, 1439, 1321, 1223, 1152, 997, 843 cm–1. 1H
NMR (400 MHz, CDCl3): δ = 7.53 (d, J = 8.8 Hz, 2 H, Ar-H),
7.39 (t, J ≈ 7.6 Hz, 1 H, Ar-H), 7.20–7.27 (m, 3 H, Ar-H), 7.00 (t,
J ≈ 7.6 Hz, 1 H, Ar-H), 6.77 (d, J = 7.6 Hz, 1 H, Ar-H), 4.32 (br.,
2 H, OCH2), 3.08 (br. s, 2 H, CH2), 1.93–1.95 (m, 2 H, CH2) ppm.
13C NMR (100 MHz, CDCl3): δ = 157.4, 146.5, 135.8, 132.5, 131.4,
130.4, 130.1, 126.6, 124.2, 123.6, 122.9, 121.5, 76.9, 25.3, 25.2 ppm.
LC–MS: m/z = 356, 358 [M]+. C17H14BrN3O (356.22): calcd. C
57.32, H 3.96, N 11.80; found C 57.48, H 3.85, N 11.69. This com-
pound was crystallized from a dichloromethane/hexane (2:1) mix-
ture at 25 °C and its X-ray structure was determined.
Compound 32: Yield 0.110 g (80%); m.p. 169–171 °C. IR (KBr): ν
˜
= 2926, 2857, 1717, 1516, 1453, 1238, 1115, 1088, 995, 922, 766
cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.28–7.34 (m, 6 H, Ar-H),
7.11 (t, J = 7.6 Hz, 1 H, Ar-H), 6.93 (d, J = 8.0 Hz, 1 H, Ar-H),
4.71 and 5.26 (2s, 4 H, 2 OCH2), 2.45 (s, 3 H, CH3) ppm. 13C
NMR (100 MHz, CDCl3): δ = 144.8, 140.0, 139.2, 134.8, 131.7,
130.3, 129.5, 128.7, 128.2, 128.0, 125.8, 125.6, 71.5, 67.8, 21.4 ppm.
LC–MS: m/z = 278 [M + 1]+. C17H15N3O (277.32): calcd. C 73.63,
H 5.45, N 15.15; found C 73.55, H 5.41, N 15.27.
Compound 38: Yield 0.101 g (61%); m.p. 172–175 °C. IR (KBr): ν
˜
= 3057, 2920, 1597, 1493, 1429, 1223, 993, 770 cm–1. 1H NMR
(400 MHz, CDCl3): δ = 7.96 (d, J = 8.8 Hz, 1 H, Ar-H), 7.90 (d,
J = 8.0 Hz, 1 H, Ar-H), 7.42–7.53 (m, 5 H, Ar-H), 7.19–7.23. (m,
1 H, Ar-H), 7.12–7.14 (m, 1 H, Ar-H), 6.67–6.71 (m, 1 H, Ar-H),
6.60 (dd, J = 8.0, 1.6 Hz, 1 H, Ar-H), 4.35 (br., 2 H, OCH2), 3.19
(br., 2 H, CH2), 1.98–2.03 (m, 2 H, CH2) ppm. 13C NMR
(100 MHz, CDCl3): δ = 157.1, 145.6, 134.1, 133.3, 132.5, 131.1,
130.3, 129.8, 129.0, 128.2, 127.8, 126.9, 125.5, 125.0, 123.9, 123.2,
122.7, 122.0, 77.3, 25.6, 25.2 ppm. LC–MS: m/z = 328 [M + 1]+.
C21H17N3O (327.38): calcd. C 77.04, H 5.23, N 12.83; found C
77.22, H 5.18, N 12.75.
Compound 33: Yield 0.113 g (64%); m.p. 178–180 °C. IR (KBr): ν
˜
= 2957, 2859, 1599, 1485, 1447, 1233, 1092, 1030, 916, 768 cm–1.
1H NMR (400 MHz, CDCl3): δ = 7.64 (d, J ≈ 8.2 Hz, 1 H, Ar-H),
7.30–7.38 (m, 3 H, Ar-H), 7.17 (t, J ≈ 7.6 Hz, 1 H, Ar-H), 7.02 (dd,
J = 7.6 Hz, J ≈ 2.2 Hz, 1 H, Ar-H), 6.94 (d, J ≈ 8.2 Hz, 1 H, Ar-
H), 5.26 (s, 2 H, OCH2), 4.72 (s, 2 H, OCH2), 2.46 (s, 3 H, CH3)
ppm. 13C NMR (100 MHz, CDCl3): δ = 145.0, 140.1, 139.3, 136.4,
133.5, 131.7, 129.7, 128.9, 128.2, 128.1, 127.9, 126.2, 125.3, 124.6,
71.5, 67.8, 23.1 ppm. LC–MS: m/z = 356, 358 [M]+. C17H14BrN3O
(356.22): calcd. C 57.32, H 3.96, N 11.80; found C 57.25, H 3.88,
N 11.91.
Compound 39: Yield 0.075 g (46%); gummy solid. IR (neat): ν =
˜
3059, 2932, 1516, 1445, 1254, 1113, 1030, 993, 835 cm–1. 1H NMR
(400 MHz, CDCl3): δ = 7.37 (t, J ≈ 7.6 Hz, 1 H, Ar-H), 7.19–7.27
(m, 3 H, Ar-H), 6.94 (t, J ≈ 7.6 Hz, 1 H, Ar-H), 6.82–6.86 (m, 3
H, Ar-H), 4.26 (t, J = 5.2 Hz, 2 H, OCH2), 3.79 (s, 3 H, OCH3),
2.70–2.73 (m, 2 H, CH2), 1.93–1.96 (m, 2 H, CH2), 1.80–1.84 (m,
2 H, CH2) ppm. 13C NMR (100 MHz, CDCl3): δ = 159.7, 157.4,
147.2, 131.7, 130.9, 130.8, 130.0, 126.0, 122.8, 121.3, 118.8, 114.2,
72.7, 55.5, 30.2, 26.7, 26.0 ppm. LC–MS: m/z = 322 [M + 1]+.
C19H19N3O2 (321.38): calcd. C 71.01, H 5.96, N 13.07; found C
71.15, H 5.88, N 13.12.
Compound 34: Yield 0.106 g (66%); m.p. 201–204 °C. IR (KBr): ν
˜
= 2978, 2868, 1595, 1512, 1458, 1285, 1252, 1086, 1063, 895, 762
cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.25–7.33 (m, 2 H, Ar-H),
7.15 (t, J ≈ 7.6 Hz, 1 H, Ar-H), 6.93–7.01 (m, 3 H, Ar-H), 6.80 (d,
J = 8.8 Hz, 1 H, Ar-H), 5.24 (s, 2 H, OCH2), 4.69 (s, 2 H, OCH2),
4.31 (m, 4 H, OCH2CH2O) ppm. 13C NMR (100 MHz, CDCl3): δ
= 144.8, 144.6, 144.1, 139.2, 131.7, 130.5, 129.4, 128.7, 128.1, 128.0,
125.6, 119.2, 118.0, 115.4, 71.5, 67.8, 64.4, 64.3 ppm. LC–MS: m/z
Compound 40: Yield 0.065 g (43%); m.p. 100–102 °C. IR (KBr): ν
˜
= 3052, 2924, 1580, 1489, 1443, 1285, 1225, 1101, 993 cm–1. 1H
NMR (400 MHz, CDCl3): δ = 7.36–7.40 (m, 1 H, Ar-H), 7.21–7.23
(m, 3 H, Ar-H), 7.13–7.15 (m, 2 H, Ar-H), 6.95 (t, J = 7.6 Hz, 1
= 322 [M + 1]+. C18H15N3O3 (321.33): calcd. C 67.28, H 4.71, N H, Ar-H), 6.83 (d, J = 7.6 Hz, 1 H, Ar-H), 4.27 (t, J ≈ 5.2 Hz, 2
13.08; found C 67.21, H 4.75, N 13.18.
H, OCH2), 2.71–2.74 (m, 2 H, CH2), 2.34 (s, 3 H, CH3), 1.94–1.95
Eur. J. Org. Chem. 2012, 2013–2022
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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2019