The Journal of Organic Chemistry
Page 16 of 31
(
1-(3,5-Dimethylphenyl)-9H-pyrrolo[1,2-a]indol-2-yl)(p-tolyl)methanone (3na): Yield: 51.5 mg, 68%;
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yellow oil; H NMR (400 MHz, CDCl ) : 7.78 (d, J = 8.0 Hz, 2H), 7.51 (s, 1H), 7.47 (t, J = 7.2 Hz,
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1H), 7.36-7.33 (m, 2H), 7.21 (d, J = 7.6 Hz, 3H), 7.05 (s, 2H), 6.85 (s, 1H), 4.05 (s, 2H), 2.41 (s, 3H),
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.29 (s, 6H); C{ H}NMR (100 MHz, CDCl ) δ: 191.2, 142.2, 139.8, 137.4, 137.3, 134.6, 134.5, 134.1,
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29.7, 128.7, 127.9, 127.8, 126.4, 126.3, 126.1, 124.7, 119.8, 117.6, 110.5, 29.4, 21.6, 21.3; HRMS
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(ESI-TOF) m/z: C H NO (M + H) calcd for 378.1852, found 378.1856.
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(1-(Naphthalen-1-yl)-9H-pyrrolo[1,2-a]indol-2-yl)(p-tolyl)methanone (3oa): Yield: 54.3 mg, 68%;
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yellow solid; mp 153.8-154.2 C (uncorrected); H NMR (400 MHz, CDCl ) : 7.88 (d, J = 8.4 Hz, 1H),
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7.83 (d, J = 7.6 Hz, 1H), 7.76 (d, J = 7.6 Hz, 1H), 7.69 (t, J = 8.4 Hz, 3H), 7.48-7.36 (m, 7H), 7.20 (t, J
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7.2 Hz, 1H), 7.07 (d, J = 8.0 Hz, 2H), 3.86-3.73 (m, 2H), 2.33 (s, 3H); C{ H}NMR (100 MHz,
CDCl ) δ: 190.9, 141.9, 140.0, 137.1, 135.6, 134.7, 133.7, 132.6, 132.0, 129.3, 128.4, 128.3, 128.0,
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127.8, 127.5, 127.2, 126.2, 125.8, 125.7, 125.4, 125.3, 124.8, 117.7, 116.9, 110.7, 29.0, 21.5; HRMS
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ESI-TOF) m/z: C H NO (M + H) calcd for 400.1700, found 400.1708.
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(1-(Thiophen-2-yl)-9H-pyrrolo[1,2-a]indol-2-yl)(p-tolyl)methanone (3pa): Yield: 45.4 mg, 64%;
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yellow oil; H NMR (400 MHz, CDCl ) : 7.82 (d, J = 8.0 Hz, 2H), 7.51 (d, J = 7.2 Hz, 1H), 7.46 (t, J =
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.2 Hz, 2H), 7.37-7.32 (m, 2H), 7.27 (s, 1H), 7.25-7.23 (m, 3H), 7.05-7.03 (m, 1H), 4.11 (s, 2H), 2.44 (s,
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H); C{ H}NMR (100 MHz, CDCl ) δ: 191.1, 142.5, 139.6, 137.4, 136.2, 134.9, 134.5, 129.8, 128.8,
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127.9, 127.2, 126.2, 125.9, 125.8, 124.9, 123.5, 118.1, 113.1, 110.7, 30.4, 21.6; HRMS (ESI-TOF) m/z:
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C H NOS (M + H) calcd for 356.1104, found 356.1110.
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(9-Methyl-1-phenyl-9H-pyrrolo[1,2-a]indol-2-yl)(p-tolyl)methanone (3sa): Yield: 55.9 mg, 77%;
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yellow oil; H NMR (400 MHz, CDCl ) : 7.78 (d, J = 8.0 Hz, 2H), 7.47-7.44 (m, 3H), 7.41 (d, J = 7.2
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Hz, 1H), 7.36-7.30 (m, 4H), 7.24-7.19 (m, 4H), 4.41-4.36 (m, 1H), 2.40 (s, 3H), 1.37 (d, J = 3H);
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C{ H}NMR (100 MHz, CDCl ) δ: 191.1, 142.2, 140.7, 139.6, 138.9, 137.2, 134.1, 129.7, 129.1, 128.7,
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27.9, 127.8, 126.4, 126.2, 125.0, 124.9, 120.1, 117.1, 110.5, 36.1, 21.5, 17.2; HRMS (ESI-TOF) m/z:
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C H NO (M + H) calcd for 364.1696, found 364.1703.
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ACS Paragon Plus Environment
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