484 Mittapelly et al.
Asian J. Chem.
OH
N
R1
N
R2
N
R1
Nano CuO
TMSN3
Toluene/H2O
rt, 5 h
N
N
OH
R2
R2
R1
N
R1
Scheme-I
(d, 2H, J = 7.9 Hz), 7.26-7.37 (m, 5H), 7.5 ( s,1H), 7.61 (d,
2H, J = 7.9 Hz). 13C NMR (75 MHz, CDCl3) δ (ppm) 21.26,
21.34, 60.19, 117.97, 125.54, 126.59, 127.93, 128.52, 128.95,
129.43, 137.88, 139.92, 147.78. ESI MS (m/z): 264 (M+H)+.
4-Phenyl-1-(1-phenyl-propyl)-1H-[1,2,3]triazole
(Table-1, entry 4): 1H NMR (300 MHz, CDCl3) δ (ppm) 0.98
(t, 3H, J = 7.6 Hz), 2.27-2.42 (m, 1H), 2.48 - 2.63 (m, 1H),
5.46 (t, 1H, J = 6.798 Hz), 7.302-7.38 (m, 8H), 7.59 (s, 1H),
7.75 (d, 2H, J = 7.6 Hz). 13C NMR (75 MHz, CDCl3) δ (ppm)
11.0, 28.36, 66.85, 118.52, 125.59, 127.02, 128.50, 128.70,
128.94, 130.68, 138.83, 147.64. ESI MS (m/z): 264.1 (M+H)+.
1-Benzhydryl-4-phenyl-1H-[1,2,3]triazole (Table-1,
entry 5): 1H NMR (300 MHz, CDCl3) δ (ppm) 6.73 (s, 1H)
7.28-7.50 (m, 12H) 7.80 (d, 2H), 7.95 (s, 1H). 13C NMR (75
MHz, CDCl3) δ (ppm) 68.09, 76.57, 77.00, 77.42, 119.57,
125.66, 128.53, 128.71, 128.88, 130.51, 138.09, 147.49. ESI
MS (m/z): 312.1 (M+H)+.
EXPERIMENTAL
All chemicals were purchased from Sigma-Aldrich and
S.D. Fine Chemicals, Pvt. Ltd. India and used as received.
ACME silica gel (100-200 mesh) was used for column
chromatography. All the other chemicals and solvents were
obtained from commercial sources and purified using standard
methods. The IR spectra of all compounds were recorded on a
Perkin-Elmer, Spectrum GX FTIR spectrometer. The 1H, 13C
NMR spectra were recorded on a Varian-400 MHz, Bruker-
Avance 300 MHz spectrometer. Chemical shifts (δ) are
reported in ppm, using TMS (δ = 0) as an internal standard in
CDCl3. ESI mass spectra were recorded on a Finnigan LCQ
Advantagemax spectrometer.
General experimental procedure:A mixture of alcohol
(1 mmol), trimethylsilyl azide (2 mmol) and CuO nanoparticles
(3 mol %) in toluene (3 mL) was stirred at 60 ºC for 3 h. After
complete consumption of the alcohol as indicated by TLC,
alkyne (1.2 mmol) and water (2 mL) was added and contin-
ued the reaction. After completion of the reaction, the reac-
tion mixture was diluted with water and extracted with ethyl
acetate (2 × 10 mL). The combined organic layers were dried
over anhydrous Na2SO4, concentrated in vacuo and purified
by column chromatography on silica gel to afford the pure
product. The product was well characterized by 1H NMR, 13C
NMR and mass spectroscopic analysis.
(E)-4-Phenyl-1-(4-phenylbut-3-en-2-yl)-1H-1,2,3-
triazole (Table-1, entry 6): 1H NMR (300 MHz, CDCl3): δ
1.85 (d, 3H, J = 6.8 Hz), 5.37-5.46 (m, 1H), 6.40 (dd, 1H, J =
6.8 Hz, 15.8 Hz), 6.60 (d, 1H, J = 15.8 Hz), 7.24-7.40 (m,
8H), 7.74 (s, 1H), 7.79 (d, 2H, J = 8.3 Hz). 13C NMR (75
MHz, CDCl3): δ 20.7, 58.4, 117.8, 125.6, 127.6, 127.9, 128.3,
128.6, 129.7, 130.6, 132.6, 135.5, 147.6. ESI MS (m/z): 276
(M+H), 298 (M + Na).
(E)-1-(4-(4-bromophenyl)but-3-en-2-yl)-4-phenyl-1H-
1,2,3-triazole (Table-1, entry 7): 1H NMR (300 MHz, CDCl3):
δ 1.86 (d, 3H, J = 6.8 Hz), 5.38-5.45 (m, 1H), 6.40 (dd, 1H,
J = 6.5 Hz, 16.1 Hz), 6.51 (d, 1H, J = 16.1 Hz), 7.22-7.30 (m,
3H), 7.36-7.40 (m, 2H), 7.44 (d, 2H, J = 8.5 Hz), 7.93 (s, 1H),
7.80 (d, 2H, J = 7.6 Hz). 13C NMR (75 MHz, CDCl3): δ 20.7,
58.3, 117.8, 122.2, 125.6, 128.1, 128.5, 128.7, 130.5, 131.4,
131.7, 134.5, 147.7. ESI MS (m/z): 354 (M)+, 256 (M + 2).
(E)-4-phenyl-1-(4-p-tolylbut-3-en-2-yl)-1H-1,2,3-
triazole (Table-1, entry 8): 1H NMR (300 MHz, CDCl3): δ
1.85 (d, 3H, J = 6.8 Hz), 2.35 (s, 3H), 5.37-5.43 (m, 1H), 6.34
(dd, 1H, J = 6.8 Hz, 15.6 Hz), 6.57 (d, 1H, J = 16.5 Hz), 7.09
(d, 2H, J = 7.8 Hz), 7.23-7.29 (m, 3H), 7.35-7.39 (m, 2H),
7.74 (s, 1H), 7.79 (d, 2H, J = 7.8 Hz). 13C NMR (75 MHz,
CDCl3): δ 20.8, 21.1, 58.4, 117.7, 125.6, 126.5, 126.6, 127.9,
128.7, 129.3, 130.6, 132.6, 132.7, 138.3, 147.6. ESI MS
(m/z): 290 (M + H).
4-Phenyl-1-(1-phenyl-ethyl)-1H-(1,2,3)triazole (Table-
1
1, entry 1): H NMR (300 MHz, CDCl3): δ (ppm) 2.03 (d,
3H, J = 7.554 Hz), 5.79-5.86 (q, 1H, J = 7.6 Hz), 7.23-7.39
(m, 8H), 7.55 (s, 1H), 7.75 (d, 2H, J = 8.309 Hz). 13C NMR
(75 MHz, CDCl3): δ (ppm) 21.23, 60.25, 118.20, 125.62,
126.52, 128.0, 128.56, 128.73, 128.99, 130.68, 139.90, 147.76.
ESI MS (m/z): 250 (M+H)+.
1-[1-(4-Bromo-phenyl)-ethyl]4-phenyl-1H-(1,2,3)
1
triazole (Table-1, entry 2): H NMR (300 MHz, CDCl3) δ
(ppm) 2.01 (d, 3H, J = 7.6 Hz) 5.75-5.82 (q, 1H, J = 7.6 Hz),
7.17 (d, 2H, J = 8.309 Hz), 7.27-7.39 (m, 3H), 7.48 (d, 2H,
J = 8.309 Hz) 7.56 (s, 1 H), 7.74 (d, 2H). 13C NMR (75 MHz,
CDCl3) δ (ppm) 21.24, 59.70, 118.21, 120.19, 125.71, 127.98,
128.18, 128.65, 128.77, 132.26, 139.80, 147.75. ESI MS
(m/z): 329 (M+2)+.
4-Phenyl-1-(1-p-tolyl-ethyl)-1H-[1,2,3]triazole (Table-
1, entry 3): 1H NMR (300 MHz, CDCl3) δ (ppm) 2.01 (d, 3H,
J = 7.2 Hz), 2.35 (s, 3H) 5.76-5.86 (q, 1H, J = 7.2 Hz), 7.12
(E)-1-(4-(4-Methoxyphenyl) but-3-en-2-yl)-4-phenyl-
1
1H-1,2,3-triazole (Table-1, entry 9): H NMR (300 MHz,