788
B. MOHTAT ET AL.
(1 H, t, 3J 8.1 Hz, CH), 7.48 (1 H, d, 3J 7.8 Hz, CH), 7.62 (1 H, t, 3J 7.8 Hz, CH), 7.97
3
3
(1 H, d, J 7.9 Hz, CH), 8.32 (1 H, d, J 8.2 Hz, CH). 13C NMR: d ¼ 30.8 (Me3C),
=
=
=
52.6 (MeO), 53.3 (MeO), 57.6 (CꢀN), 106.8 (CH ), 125.1 (CH ), 126.2 (CH ),
=
126.8 (C ), 127.1 (CH ), 128.6 (CH ), 130.3 (CH ), 133.3 (CH ), 137.6 (C ),
=
=
=
=
=
=
143.5 (C ), 152.6 (C N), 162.5 (C O), 164.6 (C O), 165.1 (C O). NMR data
=
=
=
=
1
for 5c (15%): H NMR: d ¼ 1.48 (9 H, s, Me3C), 3.70 (3 H, s, MeO), 3.76 (3 H, s,
3
MeO), 5.85 (1 H, s, CH), 6.52 (1 H, d, J 7.5 Hz, CH), 7.32 (1 H, d, J 7.5 Hz,
3
3
3
3
CH), 7.44 (1 H, t, J 7.8 Hz, CH), 7.52 (1 H, d, J 7.8 Hz, CH), 7.63 (1 H, t, J
7.7 Hz, CH), 8.38 (1 H, d, 3J 7.9 Hz, CH). 13C NMR: d ¼ 30.5 (CMe3), 52.2
=
=
(OMe), 53.3 (OMe), 59.9 (CN), 61.1 (CH), 62.9 (C C N), 106.3 (CH ), 126.3
=
=
(CH ), 126.8 (CH ), 128.2 (CH ), 131.7 (CH ), 132.7 (CH ), 133.3 (C ), 137.6
=
=
=
=
=
=
(C ), 162.2 (C O), 165.9 (C O), 168.8 (C O), 170.6 (C C N).
=
=
=
= =
Di-t-butyl 2-{(t-butylimino)[1-oxoisoquinolin-1(2H)-yl]methyl}but-2-
enedioate (4d) and di-t-butyl 2-{(t-butylimino-methylene)-3-[2-oxoisoquino-
lin-1(2H)-yl]}succinate (5d). Yellow oil. IR (KBr) (tmax=cmꢀ1): 2061 (C C N),
=
=
=
=
=
=
=
1742 (C O), 1709 (C O), 1658 (C O), 1654 (C O), 1626 (C N). MS (EI, 70 eV):
m=z (%): 454 (Mþ, 2), 310 (24), 254 (23), 198 (35), 145 (82), 57 (100), 41 (30). Anal.
calcd. for C26H34N2O5 (454.57): C, 68.70; H, 7.54; N, 6.16. Found: C, 68.73; H, 7.50;
1
N, 6.12. NMR data for 4d (63%): H NMR: d ¼ 1.32 (9 H, s, Me3C), 1.35 (9 H, s,
3
Me3C), 1.59 (9 H, s, Me3C), 6.50 (1 H, d, J 7.8 Hz, CH), 6.71 (1 H, s, CH), 7.41
3
(1 H, t, J 7.9 Hz, CH), 7.47 (1 H, d, J 7.6 Hz, CH), 7.60 (1 H, t, J 7.8 Hz, CH),
3
3
8.04 (1 H, d, J 7.9 Hz, CH), 8.35 (1 H, d, J 8.1 Hz, CH). 13C NMR: d ¼ 28.2
3
3
(Me3C), 28.4 (Me3C), 30.9 (Me3C), 57.2 (C-N), 81.9 (CꢀO), 82.9 (CꢀO), 106.3
=
(CH ), 126.0 (CH ), 126.9 (CH ), 127.0 (CH ), 127.1 (C ), 128.8 (CH ), 130.3
=
=
=
=
=
=
(CH ), 133.0 (CH ), 137.6 (C ), 143.5 (C ), 143.9 (C N), 162.3 (C O), 163.2
=
=
=
=
=
1
=
=
(C O), 164.2 (C O). NMR data for 5d (24%): H NMR: d ¼ 1.23 (9 H, s, Me3C),
3
1.43 (9 H, s, Me3C), 1.56 (9 H, s, Me3C), 5.66 (1 H, s, CH), 6.48 (1 H, d, J
3
7.5 Hz, CH), 7.43 (1 H, d, J 7.5 Hz, CH), 7.45 (1 H, t, J 7.8 Hz, CH), 7.50 (1 H,
3
d, J 7.8 Hz, CH), 7.62 (1 H, t, J 7.8 Hz, CH), 8.41 (1 H, d, 3J 7.9 Hz, CH).
3
3
13C-NMR: d ¼ 28.3 (Me3C), 28.7 (Me3C), 30.6 (Me3C), 60.1 (CꢀN), 62.5 (CH),
=
=
=
=
64.2 (C C N), 81.0 (CꢀO), 82.8 (CꢀO), 105.8 (CH ), 126.1 (CH ), 126.3
=
=
(CH ), 126.7 (CH ), 128.4 (CH ), 131.5 (CH ), 132.5 (C ), 137.6 (C ), 162.1
=
=
=
=
=
(C O), 167.5 (C O), 167.6 (C O), 169.0 (C C N).
=
=
= =
Dimethyl
2-{(cyclohexylimino)[2-oxopyridin-1(2H)-yl]methyl}but-2-
enedioate (4e). Yellow powder; yield: 0.54 g (78%), mp 164–168 ꢁC. IR (KBr)
(tmax=cmꢀ1): 1725 (C O), 1664 (C O), 1595 (C N). MS (EI, 70 eV): m=z (%):
346 (Mþ, 11), 252 (100), 170 (92), 138 (20), 83 (48), 55 (38), 41 (26). Anal. calcd.
for C18H22N2O5 (346.38): C, 62.42; H, 6.40; N, 8.09. Found: C, 62.39; H, 6.44;
N, 8.01. H NMR: d ¼ 1.26–1.88 (10 H, m, 5 CH2), 3.27 (1 H, m, HC-N), 3.65
=
=
=
3
3
(3 H, s, MeO), 3.89 (3 H, s, MeO), 6.24 (1 H, t, J 7.1, CH), 6.40 (1 H, d, J
3
3
9.2 Hz, CH), 6.79 (1 H, s, CH), 7.32 (1 H, t, J 9.2 Hz, CH), 8.01 (1 H, d, J
7.1 Hz, CH). 13C NMR: d ¼ 23.9 (CH2), 24.0 (CH2), 25.5 (CH2), 32.8 (2 CH2),
=
=
52.2 (MeO), 52.9 (MeO), 60.4 (CꢀN), 106.0 (CH ), 121.3 (CH ), 124.7
=
(CH ), 135.7 (CH ), 140.7 (CH ), 140.8 (C ), 147.5 (C N), 162.2 (C O),
=
=
=
=
=
=
=
163.3 C O), 164.4 (C O).