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N. Yu. Gorobets et al. / Tetrahedron 60 (2004) 8633–8644
analytical sample). Anal. Calcd (C15H13N3O3): C, 63.60; H,
4.63; N, 14.83. Found: C, 63.72; H, 4.26; N, 14.60; 1H NMR
(DMSO-d6) d 2.06 (quintet, J¼6.1 Hz, 2H), 2.51 (t,
J¼6.6 Hz 2H), 2.93 (t, J¼5.8 Hz, 2H), 7.15 (t, J¼6.1 Hz,
1H), 7.83 (t, J¼7.8 Hz, 1H), 8.26 (d, J¼8.3 Hz, 2H), 8.34
(d, J¼4.6 Hz, 1H), 8.77 (s, 1H), 12.04 (s, 1H), 13.12 (br s,
1H); MS (pos. APCI) m/z 284 (Mþ1); IR (KBr), cm21: n
1433, 1530, 1633, 1680, 3245.
2H), 7.20–7.44 (m, 5H), 8.66 (s, 1H), 9.72 (t, J¼5.8 Hz,
1H), 12.90 (s, 1H); 13C NMR (DMSO-d6) d 28.1, 33.1, 42.8,
50.5, 113.0, 118.8, 127.4, 127.8, 128.9, 139.7, 140.3, 159.1,
163.1, 163.6, 193.7; MS (pos. APCI) m/z 325 (Mþ1); IR
(KBr), cm21: n 1398, 1570, 1667, 2958, 2958, 3091.
4.4.12. N3-(4-Fluorophenethyl)-7,7-dimethyl-2,5-dioxo-
1,2,4a,5,6,7,8,8a-octahydro-3-quinolinecarboxamide
(15dF). Mp 251 8C. Anal. Calcd (C20H21FN2O3) C, 67.40;
H, 5.94; N, 7.86. Found: C, 67.47; H, 5.86; N, 7.90;
1H NMR (DMSO-d6) d 1.01 (s, 6H), 2.39 (s, 2H), 2.77
(s, 2H), 2.80 (t, J¼7.2 Hz 2H), 3.52 (q, J¼7.2 Hz, 2H),
7.07–7.12 (m, 2H), 7.25–7.29 (m, 2H), 8.61 (s, 1H), 9.36
(s, 1H), 12.80 (s, 1H); 13C NMR (DMSO-d6) d 28.1, 33.0,
34.7, 39.2, 40.7, 50.5, 112.9, 115.4 (d, J¼20.8 Hz), 118.9,
130.9 (d, J¼7.6 Hz), 135.9, 140.0, 158.9, 161.3 (d,
J¼239.9 Hz), 162.9, 163.5, 193.7; MS (pos. APCI) m/z
357 (Mþ1); IR (KBr), cm21: n 1508, 1557, 1618, 1678,
2361, 3057.
4.4.7. 7,7-Dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-
quinolinecarbonitrile (15dA). The product was obtained
by decomposition of salt 22dA (100 mg, 0.38 mmol) in
DMF (0.5 mL) with conc. HCl (0.5 mL) at room tempera-
ture. After addition of 1 mL water the mixture was filtered
and the product washed with Et2O (2£1 mL). Yield: 85%,
mp 310–311 8C (lit.45 298 8C); 1H NMR (CDCl3) d 1.19 (s,
6H), 2.50 (s, 2H), 2.90 (s, 2H), 8.51 (s, 1H), 12.60 (b s, 1H);
IR (KBr), cm21: n 955, 1154, 1407, 1597, 1669, 2218, 2785,
2947, 3000, 3055.
4.4.8. Methyl-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexa-
hydro-3-quinolinecarboxylate (15dB). The compound
was obtained as white solid by a solvent free protocol
under microwave conditions at 100 8C for 5 min (yield
53%), mp 232 8C. Anal. Calcd (C13H15NO4): C, 62.64; H,
4.4.13. N3-Phenyl-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-
hexahydro-3-quinolinecarboxamide
(15dG).
Mp
332 8C. Anal. Calcd (C18H18N2O3): C, 69.66; H, 5.85;
N, 9.03. Found: C, 69.87; H, 5.74; N, 9.19; 1H
NMR (DMSO-d6) d 1.04 (s, 6H), 2.44 (s, 2H), 2.85
(s, 2H), 7.12 (t, J¼7.5 Hz, 1H), 7.37 (t, J¼7.7 Hz, 2H), 7.69
(d, J¼7.9 Hz, 2H), 8.73 (s, 1H), 11.64 (s, 1H); MS (pos.
APCI) m/z 311 (Mþ1); IR (KBr), cm21: n 1392, 1484,
1599, 1626, 1683, 2751, 2799, 2876, 2920, 2965, 3012,
3027, 3081.
1
6.07; N, 5.62. Found: C, 62.86; H, 6.07; N 5.56; H NMR
(CDCl3) d 1.16 (s, 6H), 2.48 (s, 2H), 2.92 (s, 2H), 3.92 (s,
3H), 8.80 (s, 1H); MS (pos. APCI) m/z 250 (Mþ1); IR
(KBr), cm21: n 1395, 1641, 1690, 1744, 2962, 3069, 3213,
3146. The same compound was obtained by a solvent free
protocol under microwave conditions at 100 8C for 5 min
(yield 53%).
4.4.14. N3-(4-Methoxyphenyl)-7,7-dimethyl-2,5-dioxo-
1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide (15dH).
Mp 300 8C dec. Anal. Calcd (C19H20N2O4) C, 67.05; H,
4.4.9. 7,7-Dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-
quinolinecarboxamide (15dC). The compound was
obtained by irradiation of 200 mg (0.7 mmol) of salt 19dC
in i-PrOH (1 mL) under microwave conditions at 150 8C for
5 min, yielding 78 mg (48%) of product, mp 346 8C dec.
1
5.92; N, 8.23. Found: C, 66.99; H, 5.95; N, 8.43; H NMR
(DMSO-d6) d 1.04 (s, 6H), 2.43 (s, 2H), 2.84 (s, 2H), 3.74 (s,
3H), 6.93 (d, J¼9.0 Hz, 2H), 7.61 (d, J¼9.0 Hz, 2H), 8.71
(s, 1H), 11.47 (s, 1H), 13.09 (s, 1H); 13C NMR (DMSO-d6)
27.2 (2Me), 37.4 (CH2-6), 41.3 (CH2-8), 50.1 (C-7), 54.4
(OMe), 111.5 (C-4a), 0114.2 (CH-30,50), 120.3 (C-3), 122.5
(CH-20,60), 131.2 (C-1 ), 139.1 (CH-4), 154.3 (C-40), 158.6
(C-8a), 160.4 (CONHAr), 161.7 (CO-2), 180.2 (CO-5); MS
(pos. APCI) m/z 341 (Mþ1); IR (KBr), cm21: n 1511, 1556,
1596, 1630, 1675, 2966.
1
(lit.45a 340 8C dec.); H NMR (DMSO-d6) d 2.39 (s, 2H),
2.79 (s, 2H), 7.67 (s, 1H), 8.62 (s, 1H), 8.66 (s, 1H), 12.74 (s,
1H); 13C NMR (DMSO-d6) d 28.1, 33.1, 50.5, 112.8, 119.4,
140.4, 159.2, 163.5, 164.5, 193.7; MS (pos. APCI) m/z 235
(Mþ1); IR (KBr), cm21: n 1407, 1598, 1669, 2874, 2958,
3350. The same compound was obtained as white solid by a
solvent free protocol under microwave conditions at 100 8C
for 5 min (yield 43%).
4.4.15. N3-(2-Pyridyl)-7,7-dimethyl-2,5-dioxo-
1,2,5,6,7,8-hexahydro-3-quinolinecarbox-amide (15dI).
The compound was obtained by irradiation of 356 mg
(1 mmol) of salt 19dI in i-PrOH (2 mL) under microwave
conditions at 150 8C for 5 min, yielding 178 mg (57%)
of product; mp 328 8C dec. Anal. Calcd (C17H17N3O3):
C, 65.58; H, 5.50; N, 13.50. Found: C, 65.71; H, 5.26;
N, 13.69. 1H NMR (DMSO-d6) d 1.04 (s, 6H), 2.44
(s, 2H), 2.85 (s, 2H), 7.16 (t, J¼6.0 Hz, 1H), 7.65 (d,
J¼7.7 Hz, 1H), 7.84 (t, J¼6.7 Hz, 1H), 8.26 (d, J¼7.8 Hz,
1H), 8.76 (s, 1H), 12.02 (s, 1H), 13.32 (br s, 1H); MS (pos.
APCI) m/z 312 (Mþ1); IR (KBr), cm21: n. 1492, 1540,
1573, 1633, 1681, 2756, 2792, 2839, 2869, 2896, 2935,
2955, 3018.
4.4.10. N3-Propyl-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-
hexahydro-3-quinolinecarboxamide (15dD). Mp 325 8C
dec. (recrystallized analytical sample). Anal. Calcd
(C15H20N2O3): C, 65.20; H, 7.30; N, 10.14. Found: C,
1
65.15; H, 7.47; N, 10.28. H NMR (DMSO-d6) d 0.88 (t,
J¼7.4 Hz, 3H), 1.01 (s, 6H), 1.49 (hextet, J¼7.2 Hz, 2H),
2.39 (s, 2H), 2.77 (s, 2H), 3.25 (quartet, J¼6.4 Hz, 2H), 8.61
(s, 1H), 9.38 (t, 1H), 12.65 (br s, 1H); MS (pos. APCI) m/z
277 (Mþ1); IR (KBr), cm21: n 1312, 1430, 1551, 1615,
1663, 2795, 2834, 2940, 2963, 3115, 3324.
4.4.11. N3-Benzyl-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-
hexahydro-3-quinolinecarboxamide (15dE). Mp 271–
273 8C. Anal. Calcd (C19H20N2O3) C, 70.35; H, 6.21; N,
8.64. Found: C, 70.55 H, 6.20 N, 8.60; 1H NMR (DMSO-d6)
d 1.02 (s, 6H), 2.41 (s, 2H), 2.80 (s, 2H), 4.53 (d, J¼5.8 Hz,
4.4.16. Methyl 3-(4-methoxyphenylcarbamoyl)-6-
methyl-2-oxo-1,2-dihydro-5-pyridinecarboxylate
(15eH). Mp 326 8C dec. Anal. Calcd (C16H16N2O5) C,