Synthesis of 1-Phenyl-2-acyl-tetrahydroisoquinolines by Intermolecular α-Amidoalkylation Reaction

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• The 1H-NMR spectra were measured at 60 MHz with Perkin-Elmer R-24B spectrometer. The data in δppm in CDCI3(TMS) are as follows: 5 1.30(t,3H, J=10), 2.70–2.90(m,2H),3.18(t, 2H, J=10),4.15(q, 2H, J=10), 6.21(s,1H), 6.57(s,1H),6.72(s,1H),6.90(s,2H),7.20(s,5H); 6a 2.72–3.05(m,2H),3.20–3.50 (m,2H),4.45 (s,2H),6.30(s,1H),6.55(s,1H),6.70(s,2H),6.85(s,1H), 7.05(s,1H),7.12(s,4H); 6b 3.00(t,2H, J=10),3.40–3.60 (m,2H),4.10(s,2H),6.55(s,1H),6.60(s,1H),6.68(s,1H), 6.95(s,2H),7.15(s,4H),9.22(s,1H)*7a 2.78–3.00 (m,2H),3.36(t,2H, J=9),5.90(s,1H),6.58(s,1H),6.69 (s,2H),6.90(s,2H),7.10(s,2H),7.18(s,2H),7.30(s,5H); 7b 2.60–2.88(m,2H),3.20(t,2H, J=9),6.22(s,1H),6.28 (s,1H),6.50(s,1H),6.69(s,2H),6.90(s,2H),7.00(s,4H), 7.20(s,1H), 7.60(s,1H),7.90(s,1H),9.70(s,1H)*8a 2.17(s,3H),2.88(t,2H, J=8),3.55(t,2H, J=9),5.85 (s, 1H),6.60(s,1H).6.80(s,2H),6.90 (s,2H),7.10 (s,4H); 8b 2.15(s,3H),3.00(t,2H, J=11),3.65(t,2H, J=10),6.55(s,1H),6.61(s,1H),6.78(s,2H),6.98 (s,1H), 7.18(s,4H), 9.60(s,1H)*9 1.29(t, 3H, J=11),2.84 (t,2H, J=9),3.32(t,2H, J=10),3.70(s,3H),3.82(s,3H), 4.15(q,2H, J=11),6.20(s,1H),6.40(s,1H),6.58(s,2H), 6.70(s,2H),6.90(s,1H),7.04(s,1H); 10 1.24(t,3H, J=11),2.75 (t,2H, J=10),3.20–3.50(m, 2H),4.08(q, 2H, J=12),6.12(s,1H),6.40(s,1H),6.58(s, 1H),6.70(s, 1H),7.00(s,4H),7.10(s,2H); 11a 1.25(t,3H, J=11),2.85 (t,2H, J=9),3.65(t,2H, J=10),4.15(q,2H, J=11),6.19 (s,1H),6.30(s,2H),6.42(s,1H),6.82(s,1H),7.02(s,2H), 7.10(s,2H),9.30 (s,1H)*11b 1.22(t,3H, J=11), 2.55–2.80 (m,2H),3.76 (t,2H, J=10),4.14 (q,2H, J =12),5.49 (d,1H, J=14),6.18(s,2H),6.48(s,1H),6.73–7.00(m,4H), 7.15(s,1H),9.10 (d, 1H, J=14)*12 1.25 (t,3H, J=12), 2.80–3.02 (m,2H), 3.60(t,2H, J=9),4.14(q, 2H, J=12), 6.02(s,1H),6.30(s,1H),6.68(s,1H),7.00(s,2H),7.10 (s,4H), 9.30(s,1H)*13 1.30(t,3H, J=12),2.86–3.04 (m,2H),3.20–3.52(m,2H),4.17(q,2H, J=11),6.40(s, 1H), 6.90(s,1H),6.99(s,1H),7.18(s,4H),7.57(d,1H, J=6), 7.95 (s, 1H); 14 2.80–3.02(m,2H),3.80–4.15(m, 2H), 6.28(s,1H),6.79(s,1H),6.99(s,2H),7.15(s,4H),7.34 (s,5H),7.50(s,1H),7.70(s,1H),8.02(s,1H),8.02(s,1H),8.80(s,1H); 15 1.28(t,3H, J=12),2.70–2.95(m,2H),3.08–3.229m,2H), 3.70(s,3H),4.15(q,2H, J=10),6.30(s,1H),6.62(s,1H), 6.78(s,1H),7.00(s,2H),7.05(s,2H),7.11(s,2H); 16 1.30(t,3H, J=10),2.60–2.80 (m,2H),3.40(t, 2H, J=8), 3.80(s,6H),4.20(q,2H, J=8),6.34(s,1H),6.69(s,1H), 6.82(d,2H, J=6),7.00–7.20(m,4H); 17 2.60–2.90(m,2H), 3.25(t,2H, J=7),3.80(s, 6H),6.35(s,1H),6.35(s,1H),6.68(s,2H), 6.80(s,1H),7.15(s,2H),7.22(s,2H),7.35(s,4H),7.90 (s,1H); 18 2.85–3.10(m,2H),3.28(t,2H, J=7),3.80 (s,6H),4.15(s,2H),6.10(s,1H),6.64(d,2H, J=8),7.18 (s,2H),7.22(s,2H),7.95(s,1H); 19 2.10(s,3H),2.50–3.00(m,2H),3.20–3.60(m,2H),3.80(s,6H),6.08(s,1H), 6.61(s,2H),6.85(s,1H),7.12(s,2H),7.21(s,1H),7.50 (s,1H); 20 2.70–3.00(m,2H),3.25–3.53(m,2H),6.55 (s,1H),6.68(s,1H),7.08(s,2H),7.18(s,5H),7.28(s,5H), 7.90(s,1H), * For the proton of phenolic hydroxyl group at ortho position
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• The M.S. spectra were recorded on a JMS-D300 spectrometer and m/e (M+) are as follows: 5 297 (C18H19NO3, 297.3); 6a 6b 301 (C17H16NO2Cl, 301.8); 7a 7b 329 (C22H19NO2, 329.4); 8a 8b 267 (C17H17NO2, 267.3); 9 357 (C20H23NO5, 357.4); 10 313 (C18H19NO4, 313.3); 11a 11b 313 (C18H19NO4, 313.3); 12 313 (C18H19NO4, 313.3); 13 358 (C18H18N2O6, 358.3); 14 395 (C26H21NO3, 395.3); 15 311 (C19H21NO3, 311.4); 16 341 (C20H23NO4, 341.4); 17 389 (C24H23NO4, 389.4); 18 346 (C19H20NO3Cl, 345.8); 19 311 (C19H21NO3, 311.4); 20 313 (C22H19NO3, 313.4)
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