Full Paper
N,1-Dibenzyl-4-butyl-1H-1,2,3-triazole-5-carboxamide (3ga):
1.31 (m, 6H), 1.27–1.21 (m, 1H), 1.17–0.95 (m, 9H), 0.92 (s, 2H), 0.90
Yield: 86 %; Pale Yellow Solid; Column Chromatography: (hexane/ (s, 2H), 0.87 (d, J = 1.8 Hz, 3H), 0.86–0.84 (m, 6H), 0.66 (s, 3H) ppm.
AcOEt – 8:2); m.p. 90.0–91.4 °C. 1H NMR (400 MHz, CDCl3) δ = 7.25–
7.18 (m, 8H), 7.10–7.08 (m, 2H), 6.00 (t, J = 5.1 Hz, 1H), 5.75 (s, 2H),
4.48 (d, J = 5.8 Hz, 2H), 2.67 (t, J = 7.8 Hz, 2H), 1.64–1.56 (m, 2H),
1.25 (sext, J = 14.7, 7.4 Hz, 2H), 0.81 (t, J = 7.3 Hz, 3H) ppm. 13C
13C NMR (101 MHz, CDCl3) δ = 158.20, 143.94, 139.78, 137.57,
135.68, 129.72, 128.91, 128.79, 128.49, 128.33, 127.93, 127.86,
122.56, 79.43, 61.91, 56.80, 56.25, 53.57, 50.13, 43.69, 42.42, 39.83,
39.64, 38.65, 37.00, 36.77, 36.30, 35.91, 31.98, 31.92, 28.35, 28.15,
NMR (101 MHz, CDCl3) δ = 159.19, 147.21, 137.17, 135.59, 129.01, 27.96, 24.40, 23.95, 22.96, 22.70, 21.14, 19.41, 18.85, 11.98 ppm.
128.88, 128.38, 128.22, 128.02, 127.81, 127.59, 53.35, 43.88, 31.53, HRMS (ESI-TOF) m/z [M + H]+ for C45H62N4O2 calculated: 691.4946,
26.14, 22.52, 13.80 ppm. HRMS (ESI-TOF) m/z [M + H]+ for C21H24N4O
found 691.4942.
calculated: 349.2023, found 349.2022.
N,1-Dibenzyl-4-(trimethylsilyl)-1H-1,2,3-triazole-5-carboxamide
(3ha): Yield: 47 %; Pale Green Solid; Column Chromatography: (hex-
ane/AcOEt – 8:2); m.p. 66.5–68.0 °C. H NMR (400 MHz, CDCl3) δ =
Acknowledgments
1
The authors gratefully acknowledge Fundação de Amparo à
Pesquisa do Estado de São Paulo (FAPESP, grants 2013/06558-
3 and 2014/50249-8), GlaxoSmithKline (GSK), Coordenação de
7.35–7.27 (m, 7H), 7.22–7.19 (m, 2H), 7.13–7.10 (m, 2H), 5.35 (s, 2H),
3.99 (d, J = 6.6 Hz, 2H), 0.31 (s, 9H) ppm. 13C NMR (101 MHz, CDCl3)
δ = 148.39, 138.27, 135.39, 133.98, 129.08, 129.03, 128.94, 128.30, Aperfeiçoamento de Pessoal de Nível Superior (CAPES) for fi-
128.06, 127.92, 127.41, 53.96, 50.17, –0.45 ppm. HRMS (ESI-TOF) m/z
nancial support and fellowships (Finance Code 001).
[M + H]+ for C20H24N4OSi calculated: 365.1792, found 365.1803.
N,1-Dibenzyl-1H-1,2,3-triazole-5-carboxamide (3ia): Yield: 98 %;
Keywords: Carbon monoxide · Aminocarbonylation ·
1,2,3-Triazoles · Pd-catalysis · Dimethyl carbonate
Pale Green Solid; Column Chromatography: (hexane/AcOEt – 8:2);
1
m.p. 83.1–85.5 °C. H NMR (400 MHz, CDCl3) δ = 7.89 (s, 1H), 7.32–
7.28 (m, 8H), 7.22–7.18 (m, 2H), 6.87–6.84 (m, 1H), 5.92 (s, 2H), 4.53
(d, J = 5.7 Hz, 2H) ppm. 13C NMR (101 MHz, CDCl3) δ = 157.95,
137.31, 135.42, 128.93, 128.85, 128.75, 128.45, 128.41, 127.94,
127.51, 127.45, 53.30, 43.73 ppm. HRMS (ESI-TOF) m/z [M + H]+ for
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C17H16N4O calculated: 293.1397, found 293.1391.
N,1-Dibenzyl-4-((4-cinnamoylphenoxy)methyl)-1H-1,2,3-tri-
azole-5-carboxamide (3ja): Yield: 73 %; Beige Solid; Column Chro-
matography: (hexane/AcOEt – 8:2); m.p. 132.8–133.7 °C. 1H NMR
(400 MHz, CDCl3) δ = 7.95–7.92 (m, 2H), 7.81 (d, J = 15.7 Hz, 1H),
7.66–7.63 (m, 2H), 7.56 (t, J = 5.4 Hz, 1H), 7.50 (d, J = 15.7 Hz, 1H),
7.44–7.41 (m, 3H), 7.40–7.37 (m, 2H), 7.34–7.30 (m, 3H), 7.25–7.21
(m, 3H), 7.16–7.13 (m, 2H), 6.86–6.82 (m, 2H), 5.95 (s, 2H), 5.35 (s,
2H), 4.53 (d, J = 5.3 Hz, 2H) ppm. 13C NMR (101 MHz, CDCl3) δ =
188.71, 160.33, 157.65, 144.67, 141.45, 136.83, 135.21, 134.99,
132.59, 130.97, 130.66, 130.44, 129.09, 129.02, 128.89, 128.56,
128.54, 128.09, 127.99, 121.67, 114.65, 62.41, 53.65, 44.25 ppm.
HRMS (ESI-TOF) m/z [M + H]+ for C33H28N4O3 calculated: 529.2234,
found 529.2225.
2-(Acetoxymethyl)-6-((1-benzyl-5-(benzylcarbamoyl)-1H-1,2,3-
triazol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl Triacetate
(3ka): Yield: 89 %; Pale Green Solid; Column Chromatography: (hex-
1
ane/AcOEt – 1:1); m.p. 51.5–52.9 °C. H NMR (400 MHz, CDCl3) δ =
7.58 (t, J = 5.8 Hz, 1H), 7.38–7.27 (m, 10H), 5.92 (q, J = 43.6, 14.2 Hz,
2H), 5.09 (t, J = 9.5 Hz, 1H), 4.97–4.87 (m, 3H), 4.70 (dd, J = 9.6,
8.1 Hz, 1H), 4.60–4.46 (m, 3H), 4.16 (dd, J = 12.4, 5.1 Hz, 1H), 3.95
(dd, J = 12.4, 2.3 Hz, 1H), 3.64 (ddd, J = 10.1, 5.1, 2.3 Hz, 1H), 2.04
(s, 3H), 2.00 (s, 3H), 1.96 (s, 3H), 1.61 (s, 3H) ppm. 13C NMR (101 MHz,
CDCl3) δ = 170.60, 170.10, 169.56, 169.52, 157.86, 142.20, 137.49,
135.31, 130.04, 128.94, 128.89, 128.57, 127.99, 127.88, 99.83, 72.44,
72.24, 71.02, 68.03, 63.17, 61.76, 53.52, 43.82, 20.81, 20.67, 20.63,
20.27 ppm. HRMS (ESI-TOF) m/z [M + H]+ for C32H36N4O11 calcu-
lated: 653.2453, found 653.2455.
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9203.
N,1-Dibenzyl-4-((cholesterol)methyl)-1H-1,2,3-triazole-5-carb-
oxamide (3la): Yield: 95 %; Brown Solid; Column Chromatography:
(hexane/AcOEt – 8:2); m.p. 125.0–126.7 °C. 1H NMR (400 MHz, CDCl3)
δ = 8.67 (t, J = 5.6 Hz, 1H), 7.39–7.35 (m, 2H), 7.34–7.27 (m, 6H),
7.24–7.21 (m, 2H), 5.98 (s, 2H), 5.22–5.20 (m, 1H), 4.79–4.72 (m, 2H),
4.56 (d, J = 5.5 Hz, 2H), 3.18 (tt, J = 11.3, 4.5 Hz, 1H), 2.10 (ddd, J =
13.1, 5.0, 2.3 Hz, 1H), 2.04–1.88 (m, 3H), 1.82 (dtd, J = 13.1, 9.4,
5.9 Hz, 1H), 1.71 (dt, J = 13.2, 3.6 Hz, 1H), 1.65–1.48 (m, 5H), 1.45–
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Eur. J. Org. Chem. 2019, 6673–6681
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