PAPER
3-Acylindoles via a One-Pot, Regioselective Friedel–Crafts Reaction
2281
13C NMR: d = 221.9, 136.5, 132.6, 131.9, 131.5, 129.4, 128.9,
127.9, 126.4, 120.2, 118.5, 103.1, 100.2.
Anal. Calcd for C16H10F3NO: C, 66.44; H, 3.48; N, 4.84. Found: C,
66.27; H, 3.34; N, 4.57.
Anal. Calcd for C15H10ClNO: C, 70.46; H, 3.94; N, 5.48. Found: C,
70.11; H, 4.07; N, 5.69.
(1H-Indol-3-yl)-(4-trifluoromethylphenyl)methanone (3t)
Mp 202–204 °C.
(1H-Indol-2-yl)-(2-methoxyphenyl)methanone (3o)
IR (neat): 3410, 1667, 1511, 1338, 1167, 1078, 815, 752 cm–1.
Mp 242–245 °C (decomp.).
1H NMR: d = 9.27 (br s, 1 H), 8.15 (s, 1 H), 7.76 (d, J = 6 Hz, 2 H),
7.61 (d, J = 6 Hz, 2 H), 7.54 (d, J = 6 Hz, 1 H), 7.32 (d, J = 6 Hz, 1
H), 7.26 (m, 1 H), 6.99 (m, 1 H).
IR (neat): 3151, 2917, 2846, 1613, 1526, 1439, 1312, 1237, 1150,
936, 745 cm–1.
1H NMR: d = 8.99 (br s, 1 NH), 8.14 (s, 1 H), 7.71 (d, J = 6 Hz, 1
H), 7.64 (d, J = 6 Hz, 1 H), 7.41 (d, J = 6 Hz, 1 H), 7.35 (m, 1 H),
7.30 (s, 1 H), 7.19 (d, J = 6 Hz, 1 H), 7.17 (t, J = 6 Hz, 1 H), 7.15 (t,
J = 6 Hz, 1 H), 3.78 (s, 1 H).
13C NMR: d = 187.3, 159.9, 131.5, 130.6, 129.5, 130.2, 128.0,
122.6, 120.4, 119.7, 118.9, 118.1, 116.5, 114.4, 111.6, 55.4.
13C NMR: d = 191.4, 134.7, 134.1, 133.4, 130.1, 127.8, 124.7,
124.0, 123.2, 121.3, 121.2, 118.3 (q), 102.7.
Anal. Calcd for C16H10F3NO: C, 66.44; H, 3.48; N, 4.84. Found: C,
66.52; H, 3.59; N, 4.49.
(1H-Indol-3-yl)pentafluorophenylmethanone (3u)
Mp 183–186 °C.
IR (neat): 3314, 1616, 1512, 1435, 1239, 1166, 1131, 988, 742 cm–1.
Anal. Calcd for C16H13NO2: C, 76.48; H, 5.21; N, 5.57. Found: C,
76.71; H, 4.92; N, 5.39.
1H NMR: d = 9.08 (br s, 1 NH), 8.45 (s, 1 H), 7.59 (d, J = 6 Hz, 1
H), 7.47 (d, J = 6 Hz, 1 H), 7.40 (m, 1 H), 7.26 (m, 1 H).
13C NMR: d = 194.4, 137.0, 136.0, 135.3, 126.1, 124.9, 123.8,
122.3, 115.3, 111.7, 104.5, 101.6, 98.8.
(1H-Indol-3-yl)-(4-methoxyphenyl)methanone (3p)
Mp 88–89 °C (lit.31 89 °C).
IR (neat): 3389, 3060, 3009, 2937, 2842, 1605, 1498, 1447, 1300,
1257, 1169, 1106, 1031, 844, 741 cm–1.
1H NMR: d = 10.08, 8.06 (s, 1 H), 7.34 (d, J = 6 Hz, 1 H), 7.25 (d,
J = 6 Hz, 1 H), 7.21 (d, J = 6 Hz, 1 H), 7.18 (d, J = 6 Hz, 1 H), 7.07
(m, 1 H), 6.97 (m, 1 H), 6.90 (d, J = 6 Hz, 1 H), 6.73 (d, J = 6 Hz, 1
H), 3.86 (s, 3 H).
Anal. Calcd for C15H6F5NO: C, 57.89; H, 1.94; N, 4.50. Found: C,
57.54; H, 2.27; N, 4.71.
(1H-Indol-3-yl)thiophen-2-ylmethanone (3v)
Mp 180–183 °C (lit.33 181 °C).
13C NMR: d = 180.3, 136.5, 132.3, 128.8, 127.2, 126.5, 126.3,
123.1, 122.1, 121.9, 119.6, 118.6, 113.6, 112.3, 111.2, 55.6.
IR (neat): 3056, 1735, 1616, 1524, 1408, 1354, 1296, 1192 cm–1.
1H NMR: d = 9.12 (br s, 1 H), 8.41 (t, J = 6 Hz, 1 H), 7.88 (d, J = 6
Hz, 1 H), 7.70 (d, J = 4 Hz, 1 H), 7.60 (d, J = 6 Hz, 1 H), 7.30 (d,
J = 6 Hz, 1 H), 7.19 (s, 1 H), 7.18 (t, J = 6 Hz, 1 H), 7.16 (t, J = 6
Hz, 1 H).
13C NMR: d = 179.0, 165.0, 157.4, 147.9, 146.4, 131.7, 131.4,
127.6, 124.0, 123.3, 122.4, 111.4, 99.7.
(1H-Indol-3-yl)-(4-nitrophenyl)methanone (3q)
Mp 233–237 °C (decomp.).32
IR (neat): 3033, 2428, 1936, 1639, 1593, 1431, 1204 cm–1.
1H NMR: d = 8.77 (br s, 1 NH), 8.34 (d, J = 6 Hz, 1 H), 8.35 (d,
J = 6 Hz, 1 H), 8.33 (s, 1 H), 8.08 (d, J = 4 Hz, 1 H), 7.96 (d, J = 6
Hz, 1 H), 7.64 (d, J = 6 Hz, 1 H), 7.56 (d, J = 6 Hz, 1 H), 7.48 (t,
J = 6 Hz, 1 H), 7.37 (t, J = 6 Hz, 1 H).
13C NMR: d = 185.4, 158.6, 131.7, 131.3, 129.5, 128.7, 128.2,
127.6, 127.0, 126.2, 125.8, 124.5, 123.6.
(1H-Indol-3-yl)pyridin-3-ylmethanone (3w)
Mp 203–207 °C (lit.34 210–211 °C).
IR (neat): 3376, 1648, 1501, 1431, 1373, 1331, 1254, 1089, 992,
800, 746 cm–1.
Anal. Calcd for C15H10N2O3: C, 67.67; H, 3.79; N, 10.52. Found: C,
67.32; H, 3.97; N, 10.75.
1H NMR: d = 9.85 (br s, 1 NH), 8.83 (d, J = 6 Hz, 1 H), 8.71 (d,
J = 6 Hz, 1 H), 7.98 (d, J = 6 Hz, 1 H), 7.68 (d, J = 6 Hz, 1 H), 7.35
(d, J = 6 Hz, 1 H), 7.24 (d, J = 6 Hz, 1 H), 6.94 (s, 1 H), 6.55 (m, 1
H), 6.42 (m, 1 H).
13C NMR: d = 181.2, 157.9, 153.1, 136.2, 134.7, 129.4, 128.4 (over-
lapping peaks), 123.8, 121.5 (overlapping peak), 108.4, 101.9.
1-(1H-Indol-3-yl)-2-phenoxyethanone (3r)
Mp 206–208 °C.
IR (neat): 3172, 3053, 2902, 2252, 2125, 1923, 1792, 1650, 1523,
1428, 1313, 1237, 1154, 1059, 936, 797, 746, 690 cm–1.
1H NMR: d = 8.51 (s, 1 NH), 8.16 (d, J = 9 Hz, 1 H), 7.51 (d, J = 6
Hz, 1 H), 7.31–7.19 (m, 5 H), 6.99–6.91 (m, 3 H), 5.29 (s, 2 H).
Anal. Calcd for C14H10N2O: C, 75.66; H, 4.54; N, 12.60. Found: C,
75.31; H, 4.16; N, 12.29.
13C NMR: d = 189.7, 158.2, 136.4, 134.0, 129.4, 125.4, 123.1,
122.0, 121.2, 120.7, 114.5, 113.4, 112.3, 69.9.
1,6-Bis-(1H-indol-3-yl)hexane-1,6-dione (3x)
Mp 284–289 °C [decomp., lit.35 290 °C (decomp.)].
Anal. Calcd for C16H13NO2: C, 76.48; H, 5.21; N, 5.57. Found: C,
76.56; H, 5.19; N, 5.70.
IR (neat): 3168, 2929, 2422, 1621, 1407, 1125, 742, 742, 595 cm–1.
1H NMR (acetone-d6): d = 10.31 (br s, 2 H), 8.26 (s, 2 H), 7.58–7.15
(m, 8 H), 2.44 (m, 4 H), 1.56 (m, 4 H).
13C NMR (acetone-d6): d = 195.9, 135.4, 134.7, 125.0, 122.3, 121.4
(overlapping peaks), 116.1 (overlapping peaks), 111.6, 102.1, 38.7,
38.4, 23.9, 23.7.
(1H-Indol-3-yl)-(3-trifluoromethylphenyl)methanone (3s)
Mp 252–255 °C.
IR (neat): 3400, 1663, 1508, 1333, 1170, 1129, 1068, 917, 815 cm–1.
1H NMR: d = 9.08 (br s, 1 H), 8.39 (s, 1 H), 8.30 (s, 1 H), 7.88 (d,
J = 6 Hz, 1 H), 7.81 (d, J = 6 Hz, 1 H), 8.06 (d, J = 6 Hz, 1 H), 7.34
(d, J = 6 Hz, 1 H), 7.24 (m, 1 H), 6.98 (m, 1 H).
Anal. Calcd for C22H20N2O2: C, 76.74; H, 5.81; N, 8.14. Found: C,
77.13; H, 5.67; N, 7.81.
13C NMR: d = 207.3, 168.5, 141.3, 134.6, 130.6, 129.8, 129.1,
127.6, 127.0, 125.4, 124.6, 124.2, 122.8, 119.3 (q), 111.6.
1-(1H-Indol-3-yl)ethanone (3y)
Mp 192–193 °C (lit.25 191–193 °C).
Synthesis 2004, No. 14, 2277–2282 © Thieme Stuttgart · New York