Aminoclay-Supported Copper Nanoparticles for 1,3-Dipolar Cycloaddition of Azides with Alkynes
Kumar et al.
Table II. Reusability of catalysta for triazole synthesis of 3b.
CDCl3ꢃ: ꢄ 29.5, 55.8, 56.2, 61.0, 110.1, 113.4, 115.9,
125.4, 129.4, 139.6, 144.5, 153.6, 160.7.
Cycle
Yieldb (%)
1
86
2
85
3
82
4
80
2.4.8. 2-(4-Benzyl-1 H-1,2,3-Triazol-1-yl)-
2-Phenylethanol (3l, Table I):
Notes: aThe reaction was performed on 1 mmol of substrate dissolved in 4 mL of
water with 5 mg of Cu-aminoclay at 60 ꢀC; bIsolated yield.
Solid, m.p. 110–112 ꢀC; IR (KBr): ꢂmax 3384, 3064, 3032,
1H NMR (300 MHz, CDCl3ꢃ: ꢄ = 2ꢅ78, (t, 2 H, J = 6 Hz),
3.65 (t, 2 H, J = 6 Hz), 5.47 (s, 2 H), 7.26-7.35 (m, 6 H);
13C NMR (300 MHz, CDCl3ꢃ: ꢄ 54.04, 61.29, 120.01,
122.27, 126.90, 128.07, 129.67, 130.2, 134.65, 139.46,
148.02; ESI–MS m/z: 203.
2926, 2855, 2361, 1605, 1547, 1492, 1453, 1358, 1224,
1
1053, 728, 699, 535 cm−1; H NMR (300 MHz, CDCl3ꢃ:
ꢄ 7.12–7.34 (m, 11 H), 5.47 (dd, J = 8ꢅ3, 3.0 Hz, 1 H),
4.48 (dd, J = 12ꢅ0, 9.0 Hz, 1 H), 3.93–4.08 (m, 4 H).
13C NMR (75 MHz, CDCl3ꢃ: ꢄ 156.0, 147.5, 130.2, 129.9,
128.8, 128.1, 125.6, 121.3, 114.4, 69.1, 68.9, 53.1, 20.4.
MS (ESI): m/z = 280 (M+H)+.
2.4.4. Ethyl 1-o-Tolyl-1 H-1,2,3-Triazole-
4-Carboxylate (3f, Table I)
Acknowledgments: A. Sravanth Kumar and T. Srinivasa
Rao thank CSIR, New Delhi for the award of fellowships.
Brown color liquid; IR (KBr): ꢂmax 3134, 2983, 2931,
1736, 1543, 1503, 1036 cm−1 1H NMR (500 MHz,
;
CDCl3ꢃ: ꢄ 1.46 (t, J= 6.8 Hz, 3 H), 2.26 (s, 3 H), 4.45
(q, J = 6ꢅ8 Hz, 2 H), 7.33–7.35 (m, 2 H), 7.37–7.39
(m, 1 H), 7.41–7.44 (m, 1 H), 8.22 (s, 1 H). 13C NMR
(75 MHz, CDCl3ꢃ: ꢄ 14.2, 17.7, 61.3, 125.9, 126.9, 128.8,
130.4, 131.5, 133.5, 135.6, 140.1, 160.6 ppm. ESI-MS:
m/z = 232 (M+H)+.
References and Notes
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1,2,3-Triazole (3g, Table I)
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Copyright: American Scientific Publishers
2862, 2808, 1494, 1453, 1096 cm−1; H NMR (500 MHz,
CDCl3ꢃ: ꢄ 1.95 (s, 3 H), 2.35 (s, 3 H), 4.62 (s, 3 H),4.75
(s, 2 H), 6.95 (s, 2 H), 7.25–7.34 (m, 5 H), 7.53 (s, 1 H);
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124.3, 127.7, 127.8, 128.3, 128.9, 133,4, 134.9, 137.7,
39.9, 145. MS (ESI): m/z = 308 (M+H)+.
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2929,2839, 1603, 1512, 1475, 1388, 1309, 1227, 1159
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3.79 (s, 3 H), 6.81–6.92 (m, 2 H), 7.21–7.40 (m, 4 H),
7.8 (d, J = 8ꢅ3, 2 H), 8.28 (s, 1 H);13C NMR (75 MHz,
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126.6, 128.0, 128.8, 130.6, 144, 8, 147.3, 153.9. MS (ESI):
m/z = 282 (M+H)+.
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H-1,2,3-Triazole-4-Carboxylate (3j, Table I)
Solid, m.p. 73–74 ꢀC; IR (KBr): ꢂmax 3164, 2996,
2924, 1739, 1625, 1519, 1476, 1217, 1040 cm−1
;
1H NMR (500 MHz, CDCl3ꢃ: ꢄ 8.86 (s, 1 H), 7.49–6.92
(m, 3 H),4.46 (q, J = 7ꢅ8 Hz, 2 H), 3.89 (s, 3 H), 3.85
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3140
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