January 2012 Synthesis of 10-Amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine-1,8-dione Derivatives
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4h: Yield: 61%; 1H-NMR (CDCl3, 300 MHz) d: 2.56–2.80
(m, 4H, C4þC5-H), 2.86–3.00 (m, 4H, C2þC7-H), 3.30–3.53
(m, 2H, C3þC6-H), 4.06 (br s, 2H, NAH), 4.96 and 4.98 (each
s, 1H, C9-H), 7.17–7.98 (m, 14H, Ph-H); IR (KBr) m: 3255
(NH), 1593 (C¼¼O); MS (70 eV) m/z (%): 506.2 (Mþ1, 100);
Anal. calcd for C31H27N3O4: C, 73.65; H, 5.38; N, 8.31.
MS (70 eV) m/z (%): 555.2 (Mþ1, 100); Anal. calcd for
C33H31ClN2O4: C, 71.41; H, 5.63; N, 5.05. Found: C, 71.35;
H, 5.69; N, 5.13.Y 4o: Yield: 50%; 1H-NMR (CDCl3, 300
MHz) d: 2.25–2.40 (m, 4H, C4þC5-H), 2.62–2.90 (m, 4H,
C2þC7-H), 3.14–3.38 (m, 2H, C3þC6-H), 3.75 (s, 3H, OCH3),
3.76 (s, 3H, OCH3), 3.79 (s, 3H, OCH3), 3.81 (s, 3H, OCH3),
4.55 (br s, 2H, NAH), 5.61 and 5.62 (each s, 1H, C9-H), 6.78–
7.43 (m, 12H, Ph-H); IR (KBr) m: 3347 (NH), 1598 (C¼¼O);
MS (70 eV) m/z (%): 581.3 (Mþ1, 100); Anal. calcd for
C35H36N2O6: C, 72.39; H, 6.25; N, 4.82. Found: C, 72.35; H,
6.33; N, 4.75.
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Found: C, 73.58; H, 5.45; N, 8.25.Y 4i: Yield: 71%; H-NMR
(CDCl3, 300 MHz) d: 2.52–2.71 (m, 4H, C4þC5-H), 3.14–3.41
(m, 4H, C2þC7-H), 3.43–3.58 (m, 2H, C3þC6-H), 3.77 (s, 3H,
OCH3), 3.82 (s, 3H, OCH3), 4.06 (br s, 2H, NAH), 5.30 and
5.34 (each s, 1H, C9-H), 7.07–7.46 (m, 13H, Ph-H); IR (KBr)
m: 3325 (NH), 1653 (C¼¼O); MS (70 eV) m/z (%): 521.3
(Mþ1, 100); Anal. calcd for C33H32N2O4: C, 76.13; H, 6.20;
N, 5.38. Found: C, 76.23; H, 6.13; N, 5.42.
4j: Yield: 82%; 1H-NMR (CDCl3, 300 MHz) d: 2.22–2.39
and 2.58–2.87 (m, 8H, C4þC5þC2þC7-H), 3.13–3.35 (m, 2H,
C3þC6-H), 5.18 (br s, 1H, NAH), 5.55 and 5.60 (each s, 1H,
C9-H), 6.87–7.64 (m, 20H, Ph-H); IR (KBr) m: 3212 (NH),
1650 (C¼¼O); MS (70 eV) m/z (%): 537.3 (Mþ1, 100); Anal.
calcd for C37H32N2O2: C, 82.81; H, 6.01; N, 5.22. Found: C,
82.75; H, 6.09; N, 5.30.
4k: Yield: 80%; 1H-NMR (CDCl3, 300 MHz) d: 2.25–2.40
and 2.62–2.92 (m, 8H, C4þC5þC2þ C7-H), 3.10–3.36 (m, 2H,
C3þC6-H), 5.09 (br s, 1H, NAH), 5.69 and 5.70 (each s, 1H,
C9-H), 6.86–7.41 (m, 19H, Ph-H); IR (KBr) m: 3306 (NH),
1642 (C¼¼O); MS (70 eV) m/z (%): 571.3 (Mþ1, 100); Anal.
calcd for C37H31ClN2O2: C, 77.81; H, 5.47; N, 4.91. Found:
C, 77.75; H, 5.53; N, 4.98.
REFERENCES AND NOTES
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B. J Med Chem 2001, 44, 3606; (b) Dzierzbicka, K.; Kolodziejczyk, A.
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J Med Chem 2003, 46, 183.
4l: Yield: 76%; 1H-NMR (CDCl3, 300 MHz) d: 2.13–2.38
(m, 4H, C4þC5-H), 2.60–2.89 (m, 4H, C2þC7-H), 3.12–3.36
(m, 2H, C3þC6-H), 3.73 (s, 6H, 2ꢂOCH3), 4.99 (br s, 2H,
NAH), 5.55 and 5.57 (each s, 1H, C9-H), 6.69–7.31 (m, 12H,
Ph-H); IR (KBr) m: 3403 (NH), 1663 (C¼¼O); MS (70 eV) m/z
(%): 555.2 (Mþ1, 100); Anal. calcd for C33H31ClN2O4: C,
71.41; H, 5.63; N, 5.05. Found: C, 71.35; H, 5.66; N, 5.15.
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1
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4m: Yield: 83%; H-NMR (CDCl3, 300 MHz) d: 2.20–2.38
(m, 4H, C4þC5-H), 2.58–2.88 (m, 4H, C2þC7-H), 3.12–3.30
(m, 2H, C3þC6-H), 3.75 (s, 3H, OCH3), 3.77 (s, 3H, OCH3),
5.01 (br s, 2H, NAH), 5.58 and 5.60 (each s, 1H, C9-H), 6.69–
7.50 (m, 12H, Ph-H); IR (KBr) m: 3340 (NH), 1639 (C¼¼O);
MS (70 eV) m/z (%): 566.3 (Mþ1, 100); Anal. calcd for
C33H31N3O6: C, 70.07; H, 5.52; N, 7.43. Found: C, 70.03; H,
5.58; N, 7.35.
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ˇ ´
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4n: Yield: 74%; 1H-NMR (CDCl3, 300 MHz) d: 2.25–2.42
(m, 4H, C4þC5-H), 2.65–2.93 (m, 4H, C2þC7-H), 3.11–3.35
(m, 2H, C3þC6-H), 3.81 (s, 3H, OCH3), 3.82 (s, 3H, OCH3),
4.55 (br s, 2H, NAH), 5.63 and 5.65 (each s, 1H, C9-H), 6.78–
7.43 (m, 12H, Ph-H); IR (KBr) m: 3484 (NH), 1656 (C¼¼O);
´
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79, 201.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet