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T. T. Kucherenko et al. / Tetrahedron 60 (2004) 211–217
isoquinolone 4a and benzyl chloride; (1.74 g, yield 78%);
mp 340 8C; [Found: C, 78.14; H, 5.11; N, 9.39. C29H23N3O2
requires C, 78.18; H, 5.20;N, 9.43%]; nmax (KBr): 3490,
3140, 3060, 2950 (N–H), 1645, 1620 (CvO), 1580, 1525,
1495, 1435, 1405 cm21; dH: 11.65 (1H, s, NH-4), 8.30 (1H,
d, J¼7.6 Hz, H-9), 7.99 (1H, d, J¼7.6 Hz, H-6), 7.64 (1H, t,
J¼7.6 Hz, H-8), 7.22 (1H, t, J¼7.6 Hz, H-7), 7.19 (2H,00d,
J¼8.0 Hz, H-300, H-500), 7.09 (2H, d, J¼8.0 Hz, H-200, H-6 ),
6.83–7.21 (5H, m, Ph), 6.50 (2H, d, J¼7.8 Hz, H-20, H-60),
4.43 (2H, d, J¼7.8 Hz, H-30, H-50), 4.41 (2H, s, NCH2), 2.38
(3H, s, 400-CH3); dC,: 96.8 (C-20.60), 88.7 (spiro-C), 79.0
(C-30.50).
291 8C; [Found: C, 61.59; H, 4.01, Br 17.73; N, 9.32.
C23H18BrN3O2: requires C, 61.62; H, 4.05; Br 17.82; N,
9.37%]; nmax (KBr): 3505, 3150, 3060, 3000 (N–H), 1670
infl., 1650, 1620 (CvO), 1580, 1505, 1435, 1405 cm21; dH:
11.73 (1H, s, NH-4), 8.29 (1H, d, J¼8.0 Hz, H-9), 7.99 (1H,
d, J¼8.0 Hz, H-6), 7.59 (1H, t, J¼8.0 Hz, H-8), 7.49 (2H, d,
J¼8.2 Hz, H-300, H-500), 7.20 (1H, t, J¼8.0 Hz, H-7), 7.11
(2H, d, J¼8.2 Hz, H-200, H-600), 6.43 (2H,0d, J¼7.2 Hz, H-20,
H-60), 4.35 (2H, d, J¼7.2 Hz, H-30, H-5 ), 3.23 (2H, q, J¼
7.8 Hz, NCH2), 0.97 (3H, t, J¼7.8 Hz, CH3).
1.4.8. 3-(4-Nitrophenyl)-2,3,4,5-tetrahydro-1H-pyrrolo-
[2,3-c]isoquinoline-1,5-dione-2-spiro-40-(10-methyl-10,40-
dihydropyridine) (7h). Obtained by Method B from
isoquinolone 4d and dimethyl sulfate as an ocher-colored
solid; (1.38 g, yield 69%); mp 319 8C; [Found: C, 65.97; H,
3.99; N, 13.92. C22H16N4O4 requires C, 66.00; H, 4.03; N,
13.99%]; nmax (KBr): 3500, 3420, 3120 (N–H), 1670 infl.,
1645, 1620 (CvO), 1575, 1485, 1415 cm21; dH: 11.96
(1H, s, NH-4),008.30 (1H, d, J¼8.2 Hz, H-9), 8.18 (2H, d,
J¼8.2 Hz, H-3 , H-500), 8.04 (1H, d, J¼8.2 Hz, H-6), 7.61
(1H, t, J¼8.2 Hz, H-8), 7.46 (2H, d, J¼8.2 Hz, 0H-200,0H-600),
7.25 (1H, t, J¼0 8.2 Hz, H-7), 6.55 (2H, br.s, H-2 , H-6 ), 4.52
(2H, br.s, H-3 , H-50), 3.06 (3H, s, NCH3).
1.4.4. 3-(4-Tolyl)-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]-
isoquinoline-l,5-dione-2-spiro-40-(10-benzoyl-10,40-di-
hydropyridine) (7d). Obtained by Method C; (1.68 g, yield
73%); mp 250 8C; [Found: C, 75.75; H, 4.58; N, 9.10.
C29H21N3O3 requires C, 75.80; H, 4.61; N, 9.14%]; nmax
(KBr): 3130, 3060, 2950 (N–H), 1670 infl., 1660, 1625
(CvO), 1585, 1525, 1455 cm21; dH: 11.88 (1H, s, NH-4),
8.28 (1H, d, J¼8.2 Hz, H-9), 8.02 (1H, d, J¼8.0 Hz, H-6),
7.63 (1H, t, J¼8.0 Hz0, H-8), 7.37–7.56 (5H, m, Ph), 7.24
(2H, d, J¼7.2 Hz, H-2 , H-60), 7.23 (2H, d, J¼8.0 Hz, H-300,
00
H-5 ), 7.19 (1H, t, J¼8.0 Hz, H-7), 7.16 (2H, d, J¼8.0 Hz,
00
H-2 , H-600), 5.03 (2H, d, J¼7.2 Hz, H-30, H-50), 2.38 (3H, s,
400-CH3).
1.4.9. 3-(4-Nitrophenyl)-2,3,4,5-tetrahydro-1H-pyrrolo-
[2,3-c]isoquinoline-l,5-dione-2-spiro-40-(10-ethyl-10,40-
dihydropyridine) (7i). Obtained by Method B from
isoquinolone 4d and ethyl iodide; (1.76 g, yield 85%); mp
291 8C; [Found: C, 66.58; H, 4.31; N, 13.47. C23H18N4O4
requires C, 66.66; H, 4.38; N, 13.52%]; nmax (KBr): 3500,
3140, 3040 (N–H), 1670 infl., 1655, 1625 (CvO), 1585,
1535, 1510, 1440, 1405 cm21; dH: 11.96 (1H, s, NH-4), 8.31
(1H, d, J¼8.2 Hz, H-9), 8.15 (2H, d, J¼8.2 Hz, H-300, H-500),
8.04 (1H, d, J¼8.2 Hz, H-6), 7.62 (1H, t, J¼8.2 Hz, H-8),
7.46 (2H, d, J¼8.2 Hz, H-200, H-600), 7.26 (1H, t, J¼08.2 Hz,
H-7), 6.59 (2H, br.s, H-2, H-6(0), 4.51 (2H, br.s, H-3 , H-50),
3.35 (2H, q, J¼7.8 Hz, NCH2), 1.08 (3H, t, J¼7.8 Hz, CH3).
1.4.5. 3-(4-Ethoxycarbonylphenyl)-2,3,4,5-tetrahydro-
1H-pyrrolo[2,3-c]isoquinoline-1,5-dione-2-spiro-40-(10-
ethyl-10,40-dihydropyridine) (7e). Obtained by Method A
from salt 5c; (1.74 g, yield 79%); mp 238 8C; [Found: C,
70.70; H, 5.21; N, 9.47. C26H23N3O4 requires C, 70.74; H,
5.25; N, 9.52%]; nmax (KBr): 3510, 3130, 3010 (N–H),
1730, 1670 infl., 1650, 1620 (CvO), 1588, 1550, 1520,
1500, 1405 cm21; dH: 11.94 (1H, s, NH-4), 8.32 (1H, d,
J¼8.0 Hz, H-9), 8.0200(1H, d, J¼8.0 Hz, H-6), 7.91 (2H, d,
J¼8.0 Hz, H-300, H-5 ), 7.60 (1H, t, J¼8.0 Hz, H-8), 7.28
(2H, d, J¼8.0 Hz, H-200, H-600), 7.22 (1H, t, J¼8.0 Hz, H-7),
6.44 (2H, 0d, J¼7.2 Hz, H-20, H-60), 4.39 (2H, d, J¼7.2 Hz,
H-30, H-5 ), 4.34 (2H, q, J¼7.8 Hz, OCH2), 3.24 (2H, q,
J¼7.8 Hz, NCH2), 1.37 (3H, t, J¼7.8 Hz, OCH2CH3), 1.03
(3H, t, J¼7.8 Hz, NCH2CH3).
References and notes
1.4.6. 3-(4-Ethoxycarbonylphenyl)-2,3,4,5-tetrahydro-
1H-pyrrolo[2,3-c]isoquinoline-1,5-dione-2-spiro-40-(10-
benzyl-10,40-dihydropyridine) (7f). Obtained by Method B
from isoquinolone 4b and benzyl chloride; (1.79 g, yield
71%); mp 301 8C; [Found: C, 73.91; H, 4.96; N, 8.29.
C31H25N3O4: requires C, 73.94; H, 5.00; N, 8.34%]; nmax
(KBr): 3500, 3140, 3020 (N–H), 1728, 1670 infl., 1650,
1620 (CvO), 1580, 1540, 1520, 1405 cm21; dH 11.85 (1H,
s, NH-4), 8.33 (1H, d, J¼8.2 Hz, H-9), 8.0200(1H, d, J¼
8.2 Hz, H-6), 7.90 (2H, d, J¼8.2 Hz, H-300, H-5 ), 7.63 (1H,
t, J¼8.2 Hz, H-8), 7.28 (2H, d, J¼8.2 Hz, H-200, H-600), 7.23
(1H, 1, J¼8.2 Hz, H-07), 6.907.21 (5H, m, Ph), 6.53 (2H, d,
J¼7.2 Hz, H-20, H-6 ), 4.43 (2H, s, NCH2), 4.39 (2H, d,
J¼7.2 Hz, H-30, H-50), 4.37 (2H, q, J¼7.8 Hz, OCH2), 1.42
(3H, t, J¼7.8 Hz, CH3).
¨
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133.
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1.4.7. 3-(4-Bromopbenyl)-2,3,4,5-tetrahydro-1H-pyrrolo-
[2,3-c]isoquinoline-1,5-dione-2-spiro-40-(10-ethyl-10,40-
dihydropyridine) (7g). Obtained by Method B from
isoquinolone 4c and ethyl iodide; (1.91 g, yield 85%); mp
10. Tolmachev, V. N. Electronic Absorption Spectra of Organic
Compounds and Running the Spectra; Vyshcha Shkola:
Khar’koy, 1974; p 85.