HETEROCYCLES, Vol. 60, No. 8, 2003
1785
13 C NMR (DMSO-d6): d 13.7, 19.5, 31.2, 38.7, 41.9, 55.2, 55.3 (2C), 55.5, 111.2, 111.8, 113.0,
113.1, 121.2, 122.7, 126.7, 127.7, 128.0, 128.2, 147.6, 148.2, 148.5, 149.1, 164.9, 169.9. Anal.
Calcd for C25H32N2O6: C, 65.77; H, 7.06; N, 6.14. Found: C, 65.91; H, 7.03; N, 6.35.
For (E)-N-butyl-3-(3,4-dimethoxyphenyl)-2-(3,4-dimethoxyphenylacetylamino)-2-propenamide [(E)-
1
1a]: mp 139.0–140.0 °C (EtOH-hexane); IR (KBr): 3310, 2956, 1641 cm–1; H NMR (500 MHz,
DMSO-d6): d 0.79 (3H, t, J= 7.3 Hz), 1.13 (2H, tq, J= 7.3, 7.3 Hz), 1.30 (2H, tt, J= 6.7, 7.3 Hz), 3.02
(2H, dt, J= 6.1, 6.7 Hz), 3.47 (2H, s), 3.69 (3H, s), 3.72 (3H, s), 3.73 (3H, s), 3.75 (3H, s), 6.76 (1H,
dd, J= 1.8, 8.5 Hz), 6.80 (1H, s), 6.81 (1H, dd, J= 1.8, 8.5 Hz), 6.84 (1H, d, J= 8.5 Hz), 6.86 (1H, d,
J= 1.8 Hz), 6.88 (1H, d, J= 8.5 Hz), 6.92 (1H, d, J= 1.8 Hz), 7.99 (1H, t, J= 6.1 Hz), 9.63 (1H, s);
13 C NMR (DMSO-d6): d 13.6, 19.5, 30.4, 38.6, 42.2, 55.2, 55.4 (2C), 55.5, 111.5, 111.6, 111.8,
113.1, 115.5, 120.8, 121.1, 128.0, 128.3, 132.2, 147.6, 147.8, 148.2, 148.5, 164.8, 169.1. Anal.
Calcd for C25H32N2O6: C, 65.77; H, 7.06; N, 6.14. Found: C, 65.46; H, 6.84; N, 5.99.
For
3-butylaminocarbonyl-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline
(2a):
mp
1
140.0–140.5 °C (EtOAc); IR (KBr): 3388, 2932, 1743, 1665 cm–1; H NMR (500 MHz, DMSO-d6): d
0.92 (3H, t, J= 7.3 Hz), 1.33 (2H, tq, J= 7.3, 7.3 Hz), 1.54 (2H, tt, J= 6.7, 7.3 Hz), 3.36 (2H, dt, J=
6.1, 6.7 Hz), 3.67 (3H, s), 3.69 (3H, s), 3.92 (6H, s), 4.56 (2H, s), 6.82 (1H, d, J= 7.9 Hz),
6.83–6.85 (1H, m), 7.12 (1H, br s), 7.56 (1H, s), 7.60 (1H, s), 8.25 (1H, s), 8.68 (1H, t, J= 6.1 Hz);
13C NMR (DMSO-d6): d 13.7, 19.6, 31.5, 38.3, 40.4, 55.3, 55.4, 55.77, 55.82, 104.5, 107.1, 111.8,
112.9, 117.2, 120.7, 123.3, 131.6, 133.0, 141.4, 147.2, 148.6, 150.7, 152.5, 157.0, 164.3. Anal.
Calcd for C25H30N2O5: C, 68.47; H, 6.90; N, 6.39. Found: C, 68.14; H, 6.82; N, 6.19.
8. The photocyclization of (Z)-1a in methanol gave the same product distribution as that derived from the
cyclization of substituted N-acetyl-a-dehydrophenylalaninamides,3 thus allowing us to discuss the rate of
the isomerization relative to the rate of the cyclization on the basis of the same reaction scheme as that
previously proposed.
9. MM2 and PM5 calculations were accomplished by using CAChe 5.0 for Windows available from Fujitsu
Ltd, 2002. N. L. Allinger, J. Am. Chem. Soc., 1977, 99, 8127; N. L. Allinger, Y. H. Yuh, and J.-
H. Lii, J. Am. Chem. Soc., 1989, 111, 8551.
10. J. A. Riddick, W. B. Bunger, and T. K. Sakano, ‘Organic Solvents,’ 4th edn., Wiley, Chichester,
1986.
11. W. E. Kreighbaum, W. F. Kavanaugh, W. T. Comer, and D. Deitchman, J. Med. Chem., 1972, 15,
1131; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1972, 94, 2874; M. P. Cava, I. Noguchi, and
K. T. Buck, J. Org. Chem., 1973, 38, 2394; E. C. Taylor and S. F. Martin, J. Am. Chem. Soc., 1974,
96, 8095; E. Prudhommeaux, G. Ernouf, O. Foussard-Blanpin, and C. Viel, Eur. J. Med. Chem., 1975,
10, 19; S. Kano, Y. Tanaka, and S. Hibino, Heterocycles, 1980, 14, 39; D. Bhattacharjee and F. D.
Popp, J. Pharm. Sci., 1980, 69, 120; A. Brossi, K. C. Rice, C. P. Mak, J. Reden, A. E. Jacobson, Y.
Nimitkitpaisan, P. Skolnick, and J. Daly, J. Med. Chem., 1980, 23, 648; A. P. Kozikowski and A.
Ames, J. Org. Chem., 1980, 45, 2548; J. R. Falck, S. Manna, and C. Mioskowski, J. Org. Chem.,
1981, 46, 3742; K. A. Walker, M. R. Boots, J. F. Stubbins, M. E. Rogers, and C. W. Davis, J. Med.
Chem., 1983, 26, 174; J. B. Hendrickson and C. Rodriguez, J. Org. Chem., 1983, 48, 3344; L. S.