Metabolites 2021, 11, 225
8 of 13
6-(4-((p-tolylamino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
(6a) Yield: 55%; Yel-
◦
low solid; m.p: 150–152 C; 1H NMR (500 MHz, DMSO-d6)
δ 8.68 (s, 1H), 8.31 (d, J = 2.3 Hz,
1H), 8.15 (d, J = 9.6 Hz, 1H), 8.11 (dd, J = 8.9, 2.5 Hz, 1H), 7.62 (d, J = 8.9 Hz, 1H), 6.91 (d,
J = 8.1 Hz, 2H), 6.63 (d, J = 9.6 Hz, 1H), 6.61 (d, J = 7.2 Hz, 2H), 5.91 (t, J = 5.7 Hz, 1H), 4.37
(d, J = 5.8 Hz, 2H), 2.15 (s, 3H); 13C NMR (125 MHz, DMSO-d6)
δ 159.9, 153.3, 147.8, 146.5,
144.0, 133.4, 129.7, 125.0, 123.8, 121.6, 119.9, 119.9, 118.3, 118.1, 113.0, 39.3, 20.5; HRMS (ESI):
m/z calcd for [M+H]+ C19H17N4O2 333.1352; found 333.1444.
6-(4-((phenylamino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
(
6b) Yield: 51%;
◦
1
Yellow solid; m.p: 159–161 C; H NMR (500 MHz, DMSO-d6)
δ 8.71 (s, 1H), 8.32 (d,
J = 2.5 Hz, 1H), 8.15 (d, J = 9.7 Hz, 1H), 8.11 (dd, J = 8.9, 2.5 Hz, 1H), 7.62 (d, J = 8.9 Hz, 1H),
7.09 (t, J = 7.8 Hz, 2H), 6.69 (d, J = 7.9 Hz, 2H), 6.63 (d, J = 9.6 Hz, 1H), 6.57 (t, J = 7.2 Hz,
1H), 6.14 (t, J = 5.7 Hz, 1H), 4.40 (d, J = 5.8 Hz, 2H); 13C NMR (125 MHz, DMSO-d6)
δ 159.9,
153.3, 148.8, 147.6, 144.0, 133.3, 129.3, 123.8, 121.6, 120.0, 119.9, 118.3, 118.1, 116.6, 112.8,
39.0; HRMS (ESI): m/z calcd for [M+H]+ C18H15N4O2 319.1195; found 319.1201.
6-(4-(((4-methoxyphenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
(
6c
)
◦
Yield: 67%; Yellow solid; m.p: 140–142 C; 1H NMR (500 MHz, DMSO-d6)
δ 8.69 (s, 1H),8.32
(d, J = 2.6 Hz, 1H), 8.15 (d, J = 9.6 Hz, 1H), 8.11 (dd, J = 8.9, 2.6 Hz, 1H), 7.62 (d, J = 8.9 Hz,
1H), 6.73 (d, J = 8.9 Hz, 2H), 6.64 (dd, J = 9.2, 4.9 Hz, 3H), 5.72 (t, J = 5.6 Hz, 1H), 4.35 (d,
J = 5.6 Hz, 2H), 3.64 (s, 3H); 13C NMR (125 MHz, DMSO-d6)
δ 159.9, 153.3, 151.5, 147.9,
144.0, 143.0, 133.4, 123.8, 121.6, 120.0, 119.9, 118.3, 118.1, 115.0, 113.9, 55.7; HRMS (ESI): m/z
calcd for [M+H]+ C19H17N4O3 349.1301; found 349.1328.
6-(4-(((4-chlorophenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
(6d) Yield:
74%; Yellow solid; m.p: 136–138 ◦C; 1H NMR (500 MHz, DMSO-d6)
δ
8.72 (s, 1H), 8.32 (d,
J = 2.5 Hz, 1H), 8.15 (d, J = 9.6 Hz, 1H), 8.11 (dd, J = 8.9, 2.6 Hz, 1H), 7.62 (d, J = 8.9 Hz, 1H),
7.11 (d, J = 8.8 Hz, 2H), 6.69 (d, J = 8.8 Hz, 2H), 6.64 (d, J = 9.6 Hz, 1H), 6.41 (t, J = 5.7 Hz,
1H), 4.39 (d, J = 5.8 Hz, 2H); 13C NMR (125 MHz, DMSO-d6)
δ 160.0, 153.3, 147.6, 147.2,
144.0, 133.3, 129.0, 123.9, 121.7, 119.9, 119.9, 118.3, 118.1, 114.2, 38.9; HRMS (ESI): m/z calcd
for [M+H]+ C18H14ClN4O2 353.0805; found 353.0823.
6-(4-(((4-bromophenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
(6e) Yield:
70%; Yellow solid; m.p: 207–209 ◦C; 1H NMR (500 MHz, DMSO-d6)
δ
8.72(s, 1H), 8.32 (d,
J = 2.4 Hz, 1H), 8.15 (d, J = 9.6 Hz, 1H), 8.11 (dd, J = 8.9, 2.5 Hz, 1H), 7.62 (d, J = 8.9 Hz,
1H), 7.22 (d, J = 8.8 Hz, 2H), 6.64 (dd, J = 9.2, 4.3 Hz, 3H), 6.44 (t, J = 5.6 Hz, 1H), 4.39 (d,
J = 5.7 Hz, 2H); 13C NMR (125 MHz, DMSO-d6)
δ 159.9, 153.3, 148.0, 147.2, 144.0, 133.3,
131.8, 123.8, 121.7, 119.9, 119.9, 118.3, 118.1, 114.7, 107.3, 38.9; HRMS (ESI): m/z calcd for
[M+H]+ C18H14BrN4O2 397.0300; found 397.1072.
6-(4-(((4-isopropylphenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
(6f)
Yield: 80%; Yellow solid; m.p: 152–155 ◦C; 1H NMR (500 MHz, DMSO-d6)
δ
8.71 (s, 1H),
8.33 (d, J = 2.5 Hz, 1H), 8.15 (d, J = 9.6 Hz, 1H), 8.12 (dd, J = 8.9, 2.6 Hz, 1H), 7.62 (d,
J = 8.9 Hz, 1H), 6.97 (d, J = 8.4 Hz, 2H), 6.62 (dd, J = 11.1, 9.1 Hz, 2H), 5.97 (t, J = 5.8 Hz,
1H), 4.37 (d, J = 5.8 Hz, 2H), 2.77–2.67 (m, 1H), 1.14 (s, J = 6.9 Hz, 6H); 13C NMR (125 MHz,
DMSO-d6)
δ 159.9, 150.4, 147.1, 144.0, 136.5, 131.1, 127.0, 123.8, 122.7, 121.7, 119.9, 118.3,
115.0, 112.8, 111.6, 38.7, 32.9, 24.7; HRMS (ESI): m/z calcd for [M+H]+ C21H20N4O2 361.1665;
found 361.1681.
6-(4-((mesitylamino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
Yellow solid; m.p: 157–159 ◦C; 1H NMR (500 MHz, DMSO-d6)
8.67 (s, 1H), 8.32 (s, 1H),
8.16 (d, J = 9.5 Hz, 1H), 8.12–8.08 (m, 1H), 7.63 (d, J = 8.8 Hz, 1H), 6.75 (s, 2H), 6.64 (d,
J = 9.6 Hz, 1H), 4.19 (s, 2H), 2.22 (s, 6H), 2.15 (s, 3H); 13C NMR (125 MHz, DMSO-d6)
159.9,
(6g) Yield: 82%;
δ
δ
153.3, 148.1, 144.0, 143.2, 133.3, 130.7, 130.3, 129.4, 123.7, 121.5, 120.0, 119.8, 118.3, 118.1,
43.3, 20.7, 18.6; HRMS (ESI): m/z calcd for [M+H]+ C21H20N4O2 361.1665; found 361.1681.
6-(4-(((4-phenoxyphenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-2H-chromen-2-one
(6h)
Yield: 71%; Yellow solid; m.p: 172–174 ◦C; 1H NMR (500 MHz, DMSO-d6)
δ
8.75 (s, 1H),
8.34 (d, J = 2.6 Hz, 1H), 8.16 (d, J = 9.6 Hz, 1H), 8.13 (dd, J = 8.9, 2.6 Hz, 1H), 7.63 (d,
J = 8.9 Hz, 1H), 7.32–7.27 (m, 2H), 7.00 (t, J = 7.3 Hz, 1H), 6.86 (d, J = 8.7 Hz, 3H), 6.73 (d,