10.1002/ejoc.201701316
European Journal of Organic Chemistry
FULL PAPER
42.9; IR (thin film) ν 3409, 2940, 2838, 1654, 1644, 1414, 1022 cm-1.
N-Benzyl-5-bromo-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide (3g).
Prepared according to general procedure from N-benzyl-5-bromo-2-
iodobenzamide8c (1g) and phenylacetylene (2a). Yield 158.1 mg (73%)
as white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.15 (t, J = 5.8 Hz, 1H),
8.84 (s, 1H), 7.95–7.88 (m, 4H), 7.68 (d, J = 8.4 Hz, 1H), 7.49 (t, J = 7.6
Hz, 2H), 7.40–7.35 (m, 1H), 7.22–7.18 (m, 5H), 4.33 (d, J = 5.8 Hz, 2H);
13C NMR (75 MHz, DMSO-d6) δ 165.3, 147.1, 138.9, 134.9, 134.1, 133.7,
131.9, 130.4, 129.5, 128.8, 128.7, 128.1, 127.6, 127.3, 125.8, 123.0,
122.9, 43.1; IR (thin film) ν 3790, 3090, 2879, 1599, 1128, 956 cm-1.
HRMS (ESI) [M+H]+ calcd. for C22H17BrN4O 433.0664, found 433.0664.
HRMS (ESI) [M+H]+ calcd. for C22H18N4O 355.1559, found 355.1558.
N-Benzyl-4,5-dimethoxy-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide
(3b). Prepared according to general procedure from N-benzyl-2-iodo-4,5-
dimethoxybenzamide8c (1b) and phenylacetylene (2a). Yield 124.3 mg
(60%) as light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.82 (t, J =
5.7 Hz, 1H), 8.74 (s, 1H), 7.89 (d, J = 7.7 Hz, 2H), 7.48 (t, J = 7.5 Hz, 2H),
7.39–7.34 (m, 1H), 7.25–7.20 (m, 7H), 4.31 (d, J = 5.7 Hz, 2H), 3.90 (s,
3H), 3.86 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.3, 150.3, 149.3,
146.6, 139.3, 130.8, 129.4, 128.6 (128.64), 128.6 (128.55), 128.0, 127.5,
127.2, 125.7, 125.5, 123.5, 111.7, 110.1, 56.6, 56.5, 43.0; IR (thin film) ν
3775, 3033, 2892, 2746, 1588, 1039, 956 cm-1. HRMS (ESI) [M+H]+
calcd. for C24H22N4O3 415.1770, found 415.1770.
N-Benzyl-3-methyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide (3h).
Prepared according to general procedure from N-benzyl-2-iodo-3-
methylbenzamide8c (1h) and phenylacetylene (2a). Yield 130.8 mg (71%)
as light yellow solid. 1H NMR (300 MHz, CDCl3) δ 7.96 (s, 1H), 7.89–7.86
(m, 2H), 7.62–7.60 (m, 1H), 7.53–7.45 (m, 4H), 7.42–7.37 (m, 1H), 7.15–
7.10 (m, 3H), 7.04–7.00 (m, 2H), 6.26 (brs, 1H), 4.29 (d, J = 5.8 Hz, 2H),
2.10 (s, 3H); 13C NMR (75 MHz, CDCl3) δ; 166.1, 148.1, 137.1, 136.5,
135.0, 133.0, 132.8, 130.6, 129.9, 128.9, 128.6, 128.5, 127.7, 126.9,
125.9, 122.7, 44.2, 17.4; IR (thin film) ν 3776, 3697, 2884, 1588, 1169,
957 cm-1. HRMS (ESI) [M+Na]+ calcd. for C23H20N4O 391.1535, found
391.1535.
N-Benzyl-5-methoxy-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide (3c).
Prepared according to general procedure from N-benzyl-2-iodo-5-
methoxybenzamide (1c) and phenylacetylene (2a). Yield 172.9 mg (90%)
as white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.01 (t, J = 5.8 Hz, 1H),
8.73 (s, 1H), 7.89 (d, J = 8.6 Hz, 2H), 7.61 (d, J = 8.6 Hz, 1H), 7.49 (t, J =
7.3 Hz, 2H), 7.37 (t, J = 7.3 Hz, 1H), 7.26–7.18 (m, 7H), 4.33 (d, J = 5.8
Hz, 2H), 3.90 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.2, 160.0,
146.6, 139.3, 134.8, 131.0, 129.4, 128.6, 128.5, 127.9, 127.7, 127.5,
127.2, 125.7, 123.5, 116.1, 114.4, 56.4, 42.9; IR (thin film) ν 3775, 3072,
2758, 1588, 1179, 1039, 957 cm-1. HRMS (ESI) [M+Na]+ calcd. for
C23H20N4O2 407.1484, found 407.1484.
N-Cyclohexyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide
(3i).
Prepared according to general procedure from N-cyclohexyl-2-
iodobenzamide15 (1i) and phenylacetylene (2a). Yield 155.9 mg (90%) as
yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.13 (s, 1H), 7.85 (d, J = 7.7
Hz, 2H), 7.70–7.68 (m, 1H), 7.58–7.53 (m, 3H), 7.47–7.42 (m, 2H), 7.39–
7.34 (m, 1H), 5.97 (d, J = 7.6 Hz, 1H), 3.77–3.74 (m, 1H), 1.75–1.71 (m,
2H), 1.58–1.48 (m, 2H), 1.31–1.19 (m, 3H), 1.09–0.91 (m, 3H); 13C NMR
(75 MHz, CDCl3) δ 165.4, 148.1, 133.8, 133.4, 130.8, 130.1, 130.0, 129.3,
128.9, 128.5, 126.2, 125.9, 122.1, 48.9, 32.4, 25.3, 24.6; IR (thin film) ν
3776, 3697, 3073, 2888, 1588, 1162, 956 cm-1. HRMS (ESI) [M+H]+
calcd. for C21H22N4O 347.1872, found 347.1872.
N-Benzyl-4-methoxy-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide (3d).
Prepared according to general procedure from N-benzyl-2-iodo-4-
methoxybenzamide14 (1d) and phenylacetylene (2a). 178.8 mg (93%) as
white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.90 (t, J = 5.7 Hz, 1H), 8.82
(s, 1H), 7.89 (d, J = 7.5 Hz, 2H), 7.63 (d, J = 8.5 Hz, 1H), 7.49 (t, J = 7.5
Hz, 2H), 7.40–7.35 (m, 1H), 7.26–7.22 (m, 7H), 4.31 (d, J = 5.7 Hz, 2H),
3.88 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 166.0, 161.4, 148.2, 137.2,
135.2, 130.9, 129.9, 128.9, 128.6, 128.5, 127.8, 127.5, 125.9, 124.8,
122.1, 115.9, 111.7, 55.9, 44.3; IR (thin film) ν 3288, 1638, 1612, 1277,
1165, 1031 cm-1. HRMS (ESI) [M+Na]+ calcd. for C23H20N4O2 407.1484,
found 407.1485.
tert-Butyl-2-(2-(4-phenyl-1H-1,2,3-triazol-1-
yl)benzamido)ethylcarbamate (3j). Prepared according to general
procedure from tert-butyl 2-(2-iodobenzamido)ethylcarbamate (1j) and
phenylacetylene (2a). Yield 195.6 mg (96%) as yellow solid. 1H NMR
(300 MHz, DMSO-d6) δ 8.87 (s, 1H), 8.52 (brs, 1H), 7.92 (d, J = 7.6 Hz,
2H), 7.67–7.64 (m, 4H), 7.47 (t, J = 7.6 Hz, 2H), 7.38–7.33 (m, 1H), 6.78
(brs, 1H), 3.13–3.09 (m, 2H), 3.00–2.98 (m, 2H), 1.35 (s, 9H); 13C NMR
(75 MHz, DMSO-d6) δ 166.6, 156.1, 146.9, 134.6, 133.3, 131.2, 130.9,
129.9, 129.4, 128.5, 125.9, 125.8, 123.1, 78.2, 28.8; IR (thin film) ν 3776,
3158, 2840, 1598, 1111, 964 cm-1. HRMS (ESI) [M+Na]+ calcd. for
C22H25N5O2 430.1855, found 430.2070.
N1,N4-Dimethyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)terephthalamide (3e).
Prepared according to general procedure from N1,N4-dimethyl-2-
iodoterephthalamide (1e) and phenylacetylene (2a). Yield 154.3 mg
(92%) as yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.95 (s, 1H), 8.71
(d, J = 4.4 Hz, 1H), 8.51 (d, J = 4.4 Hz, 1H), 8.11–8.04 (m, 2H), 7.94 (d, J
= 7.7 Hz, 2H), 7.73 (d, J = 7.9 Hz, 1H), 7.50 (t, J = 7.7 Hz, 2H), 7.40–7.36
(m, 1H), 2.82 (d, J = 4.4 Hz, 3H), 2.65 (d, J = 4.4 Hz, 3H); 13C NMR (75
MHz, DMSO-d6) δ 166.5, 165.2, 147.0, 136.8, 135.4, 134.5, 130.7, 129.6,
129.5, 128.7, 128.5, 125.8, 124.5, 123.0, 26.8, 26.5; IR (thin film) ν 3776,
3073, 2884, 2746, 1588, 1169, 957 cm-1. HRMS (ESI) [M+H]+ calcd.
C18H17N5O2 336.1460, found 336.1460.
N-(4-Methoxybenzyl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide
(3k). Prepared according to general procedure from 2-iodo-N-(4-
methoxybenzyl)benzamide16 (1k) and phenylacetylene (2a). Yield 155.7
1
mg (81%) as pale solid. H NMR (300 MHz, DMSO-d6) δ 8.94 (t, J = 5.7
Hz, 1H), 8.77 (s, 1H), 7.88 (d, J = 7.6 Hz, 2H), 7.68–7.65 (m, 4H), 7.48 (t,
J = 7.4 Hz, 2H), 7.39–7.36 (m, 1H), 7.09 (d, J = 8.4 Hz, 2H), 6.73 (d, J =
8.4 Hz, 2H), 4.24 (d, J = 5.7 Hz, 2H), 3.65 (s, 3H); 13C NMR (75 MHz,
CDCl3) δ 166.1, 159.0, 148.1, 133.9, 132.9, 131.1, 130.1, 130.0, 129.3,
129.1, 128.9, 128.5, 126.3, 125.9, 122.0, 114.0, 55.1, 43.7; IR (thin film)
ν 3775, 3073, 2888, 1588, 1162, 1040, 956 cm-1. HRMS (ESI) [M+H]+
calcd. For C23H20N4O2 385.1665, found 385.1664.
N-Benzyl-4-chloro-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide (3f).
Prepared according to general procedure from N-benzyl-4-chloro-2-
iodobenzamide8c (1f) and phenylacetylene (2a). Yield 136.1 mg (70%) as
light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 9.08 (t, J = 5.8 Hz, 1H),
8.91 (s, 1H), 7.91–7.88 (m, 3H), 7.77–7.69 (m, 2H), 7.50 (t, J = 7.7 Hz,
2H), 7.41–7.36 (m, 1H), 7.22–7.18 (m, 5H), 4.33 (d, J = 5.8 Hz, 2H); 13C
NMR (75 MHz, DMSO-d6) δ 166.0,147.1, 139.0, 135.5, 135.3, 132.0,
131.0, 130.5, 130.0, 128.8, 128.7, 127.6, 127.3, 125.8, 123.1, 43.0; IR
(thin film) ν 3778, 3694, 3068, 2883, 1587, 1118, 951 cm-1. HRMS (ESI)
[M+H]+ calcd. for C22H17ClN4O 389.1169, found 389.1169.
N-Phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzamide (3l). Prepared
according to general procedure from 2-iodo-N-phenylbenzamide8c (1l)
1
and phenylacetylene (2a). Yield 115.7 mg (68%) as white solid. H NMR
(300 MHz, CDCl3) δ 8.20 (brs, 1H), 8.13 (s, 1H), 7.85–7.78 (m, 3H),
7.61–7.58 (m, 2H), 7.55–7.50 (m, 1H), 7.44–7.34 (m, 5H), 7.27–7.22 (m,
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