JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Synthesis of Octahydroquinazolinones/thiones
min. The catalyst was separated by filtration. The solvent
was removed by distillation, then washed with cold water
and recrystallized from methanol to afford the pure prod-
uct.
Found: C, 69.22; H, 5.92; N, 11.41%.
Compound 4n
IR (KBr): 3302 (s), 3190 (s), 1688 (s), 1667 (s), 1636
(s) cm-1; 1H NMR (DMSO-d6, 400 MHz) d: 1.35-1.61 (2H,
m, CH2), 1.74-1.91 (2H, m, CH2), 1.96-2.18 (2H, m, CH2),
3.50 (1H, s, OCH3), 4.39 (1H, s, CH), 6.56-6.65 (4H, m,
Arom), 6.96 (1H, s, NH), 8.11 (1H, s, NH) ppm; 13C NMR
(DMSO-d6, 100 MHz) d: 20.99 (CH2), 29.00 (CH2), 37.27
(CH2), 55.02 (CH), 101.62 (C), 110.42 (CH), 111.48 (CH),
119.84 (CH), 126.56 (CH), 129.25 (CH), 131.70 (CH),
156.55 (C), 169.11 (CO), 196.02 (CO) ppm; Anal. Calcd.
for C15H16N2O3: C, 66.16; H, 5.92; N, 10.29%. Found: C,
66.40; H, 5.752; N, 10.11%.
Compound 4b
IR (KBr): 3285 (s), 3200 (s), 1640 (s), 1605 (s) cm-1;
1H NMR (DMSO-d6, 400 MHz) d: 0.911 (3H, s, CH3),
1.041 (3H, s, CH3), 1.97-2.19 (2H, m, CH2), 2.30-2.51 (2H,
m, CH2), 3.66 (3H, s, OCH3), 4.76 (1H, s, CH), 7.07-6 (m,
4H, Arom), 7.76 (1H, s, NH), 9.27 (1H, s, NH) ppm; 13C
NMR (DMSO-d6, 100 MHz) d: 27.34 (CH3), 29.16 (CH3),
31.56 (C), 32.75 (CH2), 50.52 (CH2), 51.84 (CH), 55.29
(OCH3), 107.84 (C), 113.39 (CH), 128.99 (CH), 135.15
(C), 149.52 (C), 153.61 (C), 157.55 (CO), 194.86 (CO)
ppm; Anal. Calcd. for C17H20N2O3: C, 67.98; H, 6.71; N,
9.33%. Found: C, 68.228; H, 6.41; N, 9.25%.
Compound 4c
Compound 4q
IR (KBr): 3437 (s), 3305 (s), 1664 (s), 1613 (s), 1589
(s) cm-1; 1H NMR (DMSO-d6, 400 MHz) d: 0.679 (3H, s,
CH3), 0.803 (3H, s, CH3), 1.82-2.01 (2H, m, CH2), 2.06-
2.22 (2H, m, CH2), 4.94 (1H, s, CH), 7.06-7.16 (4H, m,
Arom), 7.61 (1H, s, NH), 9.35 (1H, s, NH) ppm; 13C NMR
(DMSO-d6, 100 MHz) d: 27.28 (CH3), 29.12 (C), 32.78
(CH2), 50.21 (CH2), 52.08 (CH), 107.25 (C),125.32 (CH),
126.25 (CH), 127.35 (CH), 130.48 (CH), 133.26 (CH),
145.90 (CH), 147.42 (C), 158.11 (CO), 193.03 (CO) ppm;
Anal. Calcd. for C16H17ClN2O2: C, 63.05; H, 5.62; N,
9.19%. Found: C, 63.22; H, 5.55; N, 9.08%.
IR (KBr): 3443 (s), 3192 (s), 1681 (s), 1665 (s), 1624
1
(s) cm-1; H NMR (DMSO-d6, 400 MHz) d: 0.74 (3H, s,
CH3), 0.81 (3H, s, CH3), 1.75-1.93 (2H, m, CH2), 2.09-2.24
(2H, m, CH2), 5.34 (1H, s, CH), 7.05-7.18 (4H, m, Arom),
7.50 (1H, s, NH), 9.33 (1H, s, NH) ppm; 13C NMR (DMSO-
d6, 100 MHz) d: 28.64 (CH3), 30.33 (C), 33.85 (CH2),
51.38 (CH), 107.41 (C), 128.99 (CH), 130.55 (CH), 131.01
(CH), 133.46 (CH), 142.79 (CH), 154.66 (C), 161.84 (CO),
194.24 (CO) ppm; Anal. Calcd. for C16H17ClN2O2: C,
63.05; H, 5.62; N, 9.19%. Found: C, 63.26; H, 5.37; N,
9.12%.
Compound 4r
IR (KBr): 3278 (s), 3162 (s), 1642 (s), 1572 (s) cm-1;
1H NMR (DMSO-d6, 400 MHz) d: 0.903 (3H, s, CH3), 1.04
(3H, s, CH3), 2.09-2.05 (2H, m, CH2), 2.21 (2H, s, CH2),
2.24 (3H, s, CH3), 5.13 (1H, s, CH), 7.09-7.15 (m, 4H,
Arom), 9.65 (1H, s, NH), 10.55 (1H, s, NH) ppm; 13C NMR
(DMSO-d6, 100 MHz) d: 20.33 (CH3), 27.34 (CH3), 29.60
(CH3), 32.75 (C), 37.84 (CH2), 50.75 (CH2), 51.51 (CH),
105.84 (C), 123.29 (CH), 129.00 (CH), 137.37 (C), 140.00
(C), 149.47 (C), 174.61 (CS), 195.06 (CO) ppm; Anal.
Calcd. for C17H20N2OS: C, 67.97; H, 6.71; N, 9.32; S,
10.67%. Found: C, 68.18; H, 6.50; N, 9.21; S, 10.45%.
Compound 4t
Compound 4h
IR (KBr): 3285 (s), 3190 (s), 1646 (s), 1605 (s) cm-1;
1H NMR (DMSO-d6, 400 MHz) d: 0.79 (3H, s, CH3), 0.879
(3H, s, CH3), 1.93-1.97 (2H, d, J = 16 Hz, CH2), 2.00-2.04
(2H, d, J = 16 Hz, CH2), 2.26 (1H, s, CH3), 4.50 (1H, s,
CH), 6.80-6.98 (4H, m, Arom), 7.06 (2H, br, NH) ppm;
Anal. Calcd. for C17H20N2O2: C, 71.81; H, 7.09; N, 9.85%.
Found: C, 72.03; H, 6.90; N, 9.72%.
Compound 4j
IR (KBr): 3228 (s), 2962 (s), 1649 (s), 1620 (s) cm-1;
1H NMR (DMSO-d6, 400 MHz) d: 1.89-1.83 (2H, m, CH2),
1.94-2.00 (2H, m, CH2), 2.30-2.34 (2H, m, CH2), 4.594
(1H, s, CH), 7.09-7.24 (5H, m, Arom), 7.51 (1H, s, NH),
9.34 (1H, s, NH) ppm; 13C NMR (DMSO-d6, 100 MHz) d:
21.00 (CH2), 27.77 (CH2), 36.75 (CH2), 50.94 (CH),
107.69 (C), 113.39 (CH), 129.03 (CH), 136.07 (C), 149.51
(C), 154.81 (C), 158.74 (CO), 191.82 (CO) ppm; Anal.
Calcd. for C14H14N2O2: C, 69.41; H, 5.82; N, 11.56%.
IR (KBr): 3262 (s), 3165 (s), 1666 (s), 1641 (s), 1584
1
(s) cm-1; H NMR (DMSO-d6, 400 MHz) d: 0.90 (3H, s,
CH3), 1.03 (3H, s, CH3), 2.08-2.21 (2H, m, CH2), 2.35-2.47
(2H, q, J = 16 Hz, CH2), 3.72 (3H, s, OCH3), 5.12 (1H, s,
CH), 6.88-6.91 (2H, m, Arom), 7.14-7.12 (2H, m, Arom),
9.64 (1H, s, NH), 10.54 (1H, s, NH) ppm; 13C NMR
(DMSO-d6, 100 MHz) d: 27.25 (CH3), 29.29 (CH3), 32.73
(C), 38.93 (CH2), 50.31 (CH2), 52.09 (CH), 55.56 (OCH3),
J. Chin. Chem. Soc. 2013, 60, 22-26
© 2013 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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