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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 11-12
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Original Articles

One-Pot Synthesis Op N-Alkyl (Aryl) N-(α-Alkoxybenzyl) and N-(α-Alkoxymethylene) Carboxamides

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Pages 2133-2139 | Received 10 Mar 1989, Published online: 24 Oct 2006

References

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  • Vogel , C. and Aebi , R. U. S. Pat., No . 3937750 . 1976 . C. A. 1976, 85, 142866; 1977, No 4070179; C. A. 1977, 86,72242; 1979, No 4160660; C. A. 1979, 91, 118677.
  • Riebel , H. J. , Eue , L. and Faust , W. Ger. Pat., No . 2930450 . 1901 . C. A. 1981, 94, 203843.
  • Zupancic , B. G. and Sopcic , M. 1982 . Synthesis , : 942
  • Vass , A. and Szalontai , G. 1986 . Synthesis , : 817
  • The 1H-NMR spectra were measured at 60 MHz with Perkin-Elmer R-24B spectrometer. The data, in ppm in CDC13 (TMS) are as follows: 4a 1.20(t, 3H, J=16Hz),3.45(q,2H, J=10Hz), 53.95(s,3H), 4.10(s,2H), 4.52 and 4.65(s,1H)∗, 7.40–7.69(M, 5H); 4b 2.85(t,2H, J=10Hz), 3.28(s,3H), 3.60 (t,2H, J=9Hz), 4.10(s,1H), 4.40(s,2H), 7.10(s,10H); 4c 3.32(a,3H), 3.72(s,2H), 4.05 and 4.10(s,1H)∗, 4.40(s,2H), 7.30(s,5H), 7.40(s,5H); 4d 3.60(s,3H), 3.80(s,2H), 4.20 and 4.38(s,1H)∗ 6.98–7.20(m,10H); 4e 3.70(s,3H), 5.28 (s,1H), 7.00(s,1H), 7.18(s,3H), 7.30(s,7H);4f 3.50(s,3H), 4.08(s,1H), 7.10(s,2H), 7.22(s,2H), 7.32(s,3H), 7.40(s,4H), 7.60(s,2H), 7.80(s,2H); 4g 1.82(s,3H), 3.53 (s,3H), 6.60–6.75(m,1H), 7.00(s,10H); 4h 3.70 (s,3H), 3.83(s,2H), 4.18 and 4.30(s,1h)∗, 7.05(s,2H), 7.25(s,3H), 7.35(s,2H), 7.90(s,1H), 8.05(s,1H); 4i 5.65(s,6H), 3.85 (s,3H), 4.17(s,2H), 4.41(s,1R), 6.52–7.30(m,8H); 4j 1.35 (s,3H), 2.45(s,1H), 3.60(s,3H), 3.72(s,2H), 7.00–7.32 (m,9H);4k 0.72(t,3H, J=11Hz), 1.35(t,3H, J=11Hz), 2.60 (q,2H, J=8Hz), 2.90(q,2H, J=9Hz), 5.40(s,3H), 3.70(s,2H), 4.20(s,1H), 6.80(s,2H), 7.05–7.30(m, 6H); 41 0.72(t,3H, J=12Hz), 1.31(t,3H, J=12Hz), 2.70–3.12(m,4H), 3.48(s,3H), 3.70(s,2H), 3.85(s,1H), 6.90(s,2H), 7.30(s,3H), 7.92(s,1H), 8.05(s,1H); 4m 1.10(t,3H, J=10Hz), 2.20(s,3H), 2.48 (q,2H, J=1Hz), 3.32(s,3H), 3.78(s,1H), 4.15(s,2H), 7.08 (s,5H), 7.25–7.90(m,3H); 4n 1.26(t,3H, J=10Hz), 3.60(q, 2H, J=8Hz), 3.76(s,2H}, 3.80(s,1H), 6.90(s,2H), 7.15(s, 8H); 40 1.35(t,3H, J=10Hz), 1.9O(s,3H), 3.90(q,2H, J=8Hz), 4.00(s,1H), 6.90(s,2H), 7.20(s,8H); 4p 3.45(s,3H), 3.90 (s,2H), 5.05(s,2H), 7.45(s,5H); 4g 2.20(s,3H), 2.25(S,3H), 3.62(s,3H), 4.10(s,2H), 5.35(s,2H), 7.00(s,2H), 7.10(s,1H); 4r 1.20(t,3H, J=15Hz), 2.25(s,3H), 2.50(q,2H, J=14Hz), 3.45(s,3H), 3.70(s,2H), 4.90(s,2H), 7.10(s, 3H); 4s 1.25(t,6H, J=12Hz), 2.55(q,4H, J=11Hz), 3.48(s,3H), 3.69(s,2H), 4.95(s,2H), 6.85(s,1H), 7.20(s,2H). ∗probably from conformeres
  • The IR spectra Were recorded on a Specord IR (C. Zeiss) spectrophotometer in CHCl3 and give °Co 1660–1680 cm−1

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