Month 2017
Microwave-accelerated Conjugate Addition of 2-Arylindoles to Substituted Β-
Nitrostyrenes in the Presence of Ammonium Trifluoroacetate
J = 8.5 Hz, 7.5 Hz, 1.0 Hz, 1H), 6.93 (br d, J = 8.0 Hz, 1H),
6.88 (t, J = 2.0 Hz, 1H), 6.77 (dd, J = 8.5 Hz, 2.5 Hz, 1H),
5.28 (dd as br t, J = 8.0 Hz, 1H), 5.16 (dd, J = 12.5 Hz,
7.0 Hz, 1H), 5.12 (dd, J = 12.5 Hz, 8.5 Hz, 1H), 3.71 (s,
3H). MS (ESI) (m/z): 373 [M + H]+. HRMS m/z calculated
for C23H20N2O3 [M]+ 372.1474, found 342.1477.
3-(1-(Naphthalen-2-yl)-2-nitroethyl)-2-phenyl-1H-indole
(10). 1H NMR (CDCl3, 500 MHz) δ 8.19 (br s, 1H, NH),
7.82–7.73 (m, 4H), 7.55 (dd, J = 8.0 Hz, 0.5 Hz, 1H),
7.50–7.40 (m, 9H), 7.23 (ddd, J = 8.0 Hz, 7.0 Hz,
1.0 Hz, 1H), 7.10 (ddd, J = 8.0 Hz, 7.0 Hz, 1.0 Hz, 1H),
5.48 (dd as t, J = 7.0 Hz, 1H), 5.32 (dd, J = 12.5 Hz,
7.0 Hz, 1H), 5.22 (dd, J = 12.5 Hz, 8.5 Hz, 1H); MS
(ESI) (m/z): 393 [M + H]+. HRMS m/z calculated for
3-(2-Nitro-1-(2-(trifluoromethyl)phenyl)ethyl)-2-phenyl-1H-
indole (5). 1H NMR (CDCl3, 500 MHz) δ 8.16 (br s, 1H,
C26H20N2O2 [M]+ 392.1525, found 392.1530.
NH), 7.83 (br d, J = 8.0 Hz, 1H), 7.76 (dd, J = 8.0 Hz,
1.0 Hz, 1H), 7.68 (dd, J = 7.5 Hz, 1.0 Hz, 1H), 7.44–7.39
(m, 5H), 7.38–7.33 (m, 3H), 7.27–7.23 (m, 1H), 7.21 (ddd,
J = 8.5 Hz, 7.5 Hz, 1.5 Hz, 1H), 5.76 (dd, J = 10.5 Hz,
5.5 Hz, 1H), 5.34 (dd, J = 13.5 Hz, 10.5 Hz, 1H), 4.89 (dd,
J = 13.5, 5.5 Hz, 1H); MS (ESI) (m/z): 410.12 [M + H]+.
MS (ESI) (m/z): 411 [M + H]+. HRMS m/z calculated for
C23H17F3N2O2 [M]+ 410.1242, found 410.1248.
3-(2-Nitro-1-(4-(piperidin-1-yl)phenyl)ethyl)-2-phenyl-1H-
indole (11). 1H NMR (DMSO-d6, 500 MHz) δ 11.41 (br
s, 1H, NH), 7.64 (d, J = 8.0 Hz, 1H), 7.59–7.41 (m, 5H),
7.37 (d, J = 8.0 Hz, 1H), 7.18–7.04 (m, 3H), 6.98 (t,
J = 7.5 Hz, 1H), 6.83 (d, J = 8.5 Hz, 2H), 5.52–5.27 (m,
2H), 5.09 (dd as t, J = 8.5, 1H), 3.17–2.95 (m, 4H),
1.67–1.36 (m, 6H); MS (ESI) (m/z): 426 [M + H]+.
HRMS m/z calculated for C27H27N3O2 [M + H]+
3-(1-(2,6-Dichlorophenyl)-2-nitroethyl)-2-phenyl-1H-indole
(6). 1H NMR (CDCl3, 500 MHz) δ 8.02 (br s, 1H, NH),
426.2103, found 426.2120.
2-(Naphthalen-2-yl)-3-(2-nitro-1-phenylethyl)-1H–indole
7.41–7.27 (m, 7H), 7.19 (d, J = 8.0 Hz, 2H), 7.17 (dd,
J = 8.0 Hz, 1.0 Hz, 1H), 7.08–7.03 (m, 2H), 6.20 (dd,
J = 8.5 Hz, 7.0 Hz, 1H), 5.27 (dd, J = 13.5 Hz, 6.5 Hz, 1H),
5.24 (dd, J = 13.0 Hz, 9.0 Hz, 1H); MS (ESI) (m/z): 411
[M + H]+. HRMS m/z calculated for C22H16Cl2N2O2 [M]+
410.0589, found 410.0585.
4-(2-Nitro-1-(2-phenyl-1H-indol-3-yl)ethyl)benzonitrile (7).
1H NMR (CDCl3, 500 MHz) δ 8.22 (br s, 1H, NH), 7.58 (d,
J = 8.5 Hz, 2H), 7.52–7.46 (m, 3H), 7.46–7.39 (m, 6H),
7.25 (ddd, J = 8.0 Hz, 7.0 Hz, 1.0 Hz, 1H), 7.14 (ddd,
J = 8.0 Hz, 7.0 Hz, 1.0 Hz, 1H), 5.36 (dd as br t,
J = 8.0 Hz, 1H), 5.23 (dd, J = 12.5 Hz, 8.0 Hz, 1H), 5.11
(dd, J = 12.5 Hz, 7.5 Hz, 1H); MS (ESI) (m/z): 368
[M + H]+. HRMS m/z calculated for C23H17N3O2 [M]+
367.1321, found 367.1323.
(12). 1H NMR (CDCl3, 500 MHz) δ 8.27 (br s, 1H, NH),
7.94 (d, J = 8.5 Hz, 1H), 7.91–7.87 (m, 2H), 7.86–7.81 (m,
1H), 7.61–7.51 (m, 4H), 7.44 (d, J = 8.0 Hz, 1H), 7.40–
7.35 (m, 2H), 7.35–7.29 (m, 2H), 7.28–7.22 (m, 2H),
7.15 (ddd, J = 8.0 Hz, 7.0 Hz, 1.0 Hz, 1H), 5.41 (dd as t,
J = 8.0 Hz, 1H), 5.21 (dd, J = 12.5 Hz, 7.5 Hz, 1H), 5.18
(dd, J = 12.5 Hz, 8.5 Hz, 1H); MS (ESI) (m/z): 393
[M + H]+. HRMS m/z calculated for C26H20N2O2 [M]+
392.1525, found 392.1530.
2-Methyl-3-(2-nitro-1-phenylethyl)-1H–indole (13).
1H
NMR (CDCl3, 500 MHz) δ 7.85 (br s, 1H, NH), 7.36
(dd, J = 8.0 Hz, 0.5 Hz, 1H), 7.34–7.25 (m, 5H), 7.24–
7.20 (m, 1H), 7.11 (ddd, J = 8.5 Hz, 7.5 Hz, 1.0 Hz, 1H),
7.02 (ddd, J = 8.0 Hz, 7.0 Hz, 1.0 Hz, 1H), 5.26–5.16
(m, 2H), 5.11 (dd, J = 10.5 Hz, 7.5 Hz, 1H), 2.40 (s,
3H); MS (ESI) (m/z): 281 [M + H]+. HRMS m/z
calculated for C17H16N2O2 [M]+ 280.1212, found
3-(2-Nitro-1-(2-nitrophenyl)ethyl)-2-phenyl-1H-indole (8). 1H
NMR (CDCl3, 500 MHz) δ 8.18 (br s, 1H, NH), 7.84 (dd,
J = 8.0 Hz, 1.5 Hz, 1H), 7.77 (dd, J = 8.0 Hz, 1.0 Hz, 1H),
7.64 (dd, J = 8.0 Hz, 0.5 Hz, 1H), 7.49 (td, J = 7.5 Hz,
1.5 Hz, 2H), 7.45–7.37 (m, 5H), 7.33–7.28 (m, 2H), 7.27–
7.22 (m, 1H), 7.18 (ddd, J = 8.0 Hz, 7.0 Hz, 1.0 Hz, 1H),
5.93 (dd, J = 9.0 Hz, 7.0 Hz, 1H), 5.30 (dd, J = 13.5 Hz,
9.0 Hz, 1H), 5.16 (dd, J = 13.5 Hz, 7.0 Hz, 1H); MS (ESI)
(m/z): 388 [M + H]+. HRMS m/z calculated for C22H17N3O4
[M + H]+ 388.1219, found 388.1223.
280.1220.
5-Nitro-3-(2-nitro-1-phenylethyl)-2-phenyl-1H-indole
(14). 1HNMR (DMSO-d6, 500MHz) δ12.27 (brs, 1H,
NH), 8.46(d, J=2.0Hz, 1H), 8.03(dd, J=9.0Hz, 2.0Hz,
1H), 7.63–7.49 (m, 6H), 7.37–7.30 (m, 4H), 7.27–7.22
(m, 1H), 5.64 (dd, J = 13.5 Hz, 7.5 Hz, 1H), 5.44 (dd,
J=13.0Hz, 9.0Hz, 1H), 5.27(ddast,J=8.0Hz,1H);MS
(ESI) (m/z): 388 [M + H]+. HRMS m/z calculated for
1H
C22H17N3O4 [M + H]+ 388.1219, found 388.1300.
2-(4-Chlorophenyl)-3-(2-nitro-1-phenylethyl)-1H–indole
(15). 1H NMR (DMSO-d6, 500 MHz): δ 11.50 (br s, 1H,
3-(1-(Furan-2-yl)-2-nitroethyl)-2-phenyl-1H-indole (9).
NMR (CDCl3, 500 MHz) δ 8.17 (br s, 1H, NH), 7.56 (dd,
J = 8.0 Hz, 0.5 Hz, 1H), 7.54–7.47 (m, 4H), 7.47–7.42 (m,
1H), 7.39 (br d, J = 8.0 Hz, 1H), 7.37 (d, J = 2.0 Hz, 1H),
7.22 (ddd, J = 8.5 Hz, 7.5 Hz, 1.5 Hz, 1H), 7.12 (ddd,
J = 8.0 Hz, 7.0 Hz, 1.0 Hz, 1H), 6.30 (dd, J = 3.5 Hz,
2.0 Hz, 1H), 6.14 (dt, J = 3.5 Hz, 1.0 Hz, 1H), 5.36 (td,
J = 7.5 Hz, 0.5 Hz, 1H), 5.24 (dd, J = 12.5 Hz, 7.5 Hz, 1H),
4.92 (dd, J = 12.5 Hz, 7.5 Hz, 1H); MS (ESI) (m/z): 333
[M + H]+. HRMS m/z calculated for C20H16N2O3 [M]+
332.1161, found 332.1168.
NH), 7.68–7.59 (m, 3H, esp. 7.63 (d, J = 8.5 Hz, 2H), 7.54
(d, J = 8.0 Hz, 2H), 7.38 (d, J = 8.0 Hz, 1H), 7.34–7.27 (m,
4H), 7.21 (tt, J = 7.0 Hz, 1.5 Hz, 1H), 7.12 (br t, J = 8.0 Hz,
1H), 6.98 (br t, J = 8.0 Hz, 1H), 5.56 (dd, J = 13.5 Hz,
7.5 Hz,1H), 5.44 (dd, J = 13.5 Hz, 9.5 Hz, 1H), 5.17 (dd
as br t, J = 8.0 Hz, 1H); MS (ESI) (m/z): 377 [M + H]+.
HRMS m/z calculated for C22H17ClN2O2 [M]+ 376.0979,
found 376.0959.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet