Synthesis of 3-Oxo-2,3-Dihydroisoquinolines from Ethyl 2-Acylphenylacetates and Formamides

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• The 1H-NMR spectra were recorded on a Tesla BS 587A 80 MHz spectometer in CDCI3 or DMSO∗ (TMS). The data in ppm are as follows: 3a 1.25(t,2H,J = 7), 2.57 (s,3H), 3.82(s,2H), 3.90(s,6H), 4.12(q,2H,J = 7), 6.62(s,1H), 7.15(s,1H); 3b 0.95(d,6H,J = 6), 1.25(t,3H,J = 6), 2.12–2.43(m,1H), 2.75(d,2H,J = 8), 3.88(s,2H), 3.95(s,6H), 4.13(q,2H,J = 6), 6.73(s,1H) 7.25(s,1H); 3c 1.12(t,3H,J = 8), 3.75(s,3H), 3.80(s,2H), 3.92(s,3H), 4.12(q,2H,J = 8), 6.83(s,1H), 6.92(s,1H), 7.40–7.83(m,5H); 3d 1.16(t,3H,J = 6), 3.75(s,3H), 3.88(s,2H), 3.95(s,3H), 4.12(q,2H,J = 8), 6.85(s,2H), 7.92(q,2H,J = 10), 8.28(d,2H,J = 10), 3e 1.25(t,3H,J = 6), 3.60(t,2H,J = 10), 3.78(s,3H), 3.85(s,2H), 3.92(s,3H), 4.10 (q,2H,J = 6), 4.18(s,2H), 6.68(s,1H), 7.15(s,1H), 7.18–7.80(m,5H); 3f 1.10(t,3H,J = 6), 3.72(s,3H), 3.80(s,2H), 3.92(s,3H), 4.10(q,2H,J = 6), 4.18(s,2H), 6.75 (s,1H), 6.80(s,1H), 6.92(s,1H), 7.50(s,1H); 4a, 1.92(s,3H), 2.50(s,1H), 3.83(s,6H), 6.48(s,1H), 6.92(s,1H), 7.08(s,1H); 4b 1.02(d,6H,J = 8), 1.98–2.30(m,1H), 3.06(d,2H,J = 7), 3.93(s,3H), 3.98(s,3H), 6.63(s,2H), 6.85 (s,1H); 4c 3.68(s,3H), 3.92(s,3H), 6.78 (s,1H), 7.08 (s,1H), 7.13(s,1H), 7.40–7.70(m,5H); 4d 3.53(s,6H), 6.82(s,1H), 6.96(s,1H), 7.08(s,1H), 7.92(d,2H,J = 8), 8.38(d,2H,J = 8); 4e 1.93(s,1H), 3.78(s,3H), 3.85 (s,3H), 4.45(s,2H), 6.63(s,1H), 7.00(s,1H), 7.12 (s,1H), 7.25(s,5H); 4f 3.78(s,3H), 3.83(s,3H), 4.55(s,2H), 6.55(s,1H), 6.98(s,1H), 7.20(s,1H), 7.46(d,2H,J = 8), 8.05(d,2H,J = 8); 4g 3.62(s,3H), 3.65(s,3H), 3.80(s,3H), 3.85(s,3H), 4.50(s,2H), 6.70 (s,2H), 7.00 (s,2H), 7.15(s,1H), 7.45(s,1H); 4h 2.62(s,3H), 3.60(s,3H), 3.75 (s,6H), 6.15(s,1H), 6.48(s,1H), 6.95(s,1H); 4i 3.38(s,3H), 3.50(s,3H), 3.80(s,3H), 5.93(s,1H), 6.39(s,1H), 6.56(s,1H), 7.10–7.48(m,5H),∗spectra of 4a-g in DMSO.
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• The M.S. spectra were recorded on a JMS-D300 spectrometer and m/z (M+) are as follows: 3a 266(C14H18O5, 266.3); 3b 308 (C17H24O5, 308.4); 3c 328 (C19H20O5, 328,4); 3d 373 (C19H19NO7, 373.4); 3e 342 (C20H22O5, 342.4); 3f 402 (C22H26O7, 402); 4a 219 (C12H13NO3, 219.2); 4b 261 (C15H19NO3, 261.3) 4c 281 (C17H15NO3, 281.3); 4d 326 (C17H14N2O5, 326.3); 4e 295 (C18H17NO3, 295.3); 4f 340 (C18H16N2O5, 340.4); 4g 355 (C20H21NO5, 355.4); 4h 233 (C13H15NO3, 233.3); 4i 295 (C18H17NO3, 295.3)
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