G Model
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References
CH3), 1.36 (s, 3H, CH3), 2.47–2.65 (m, 4H, 2 Â CH2), 2.85 (s,
3H, CH3), 3.84 (s, 3H, OCH3), 5.06 (s, 1H, CH), 6.30 (s, 1H,
NH), 7.54 (t, J = 8.0 Hz, 2H, Ar-H), 7.79 (d, J = 8.0 Hz, 2H, Ar-
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107.66, 111.28, 121.32, 131.09, 132.56, 134.89, 134.33 (q,
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d
: À110.5. MS (EI), m/z (%) = 393 (M+, 7),
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C
C
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4.3.6. Methyl 4-(biphenyl-4-yl)-2,7,7-trimethyl-5-oxo-
1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (5m)
0.360 g (90%); pale yellow solid; mp 267–269 8C; IR
(KBr) (
y
max/cmÀ1): 3531, 3079, 2976, 2881, 1731, 1710,
1536, 1443, 776, 734; 1H NMR (CDCl3, 500 MHz)
d
: 1.07 (s,
3H, CH3), 1.12 (s, 3H, CH3), 2.34–2.56 (m, 4H, 2 Â CH2), 2.67
(s, 3H, CH3), 3.87 (s, 3H, OCH3), 5.23 (s, 1H, CH), 6.35 (s, 1H,
NH), 7.17 (d, J = 7.5 Hz, 2H, Ar-H), 7.24 (d, J = 8.0 Hz, 2H, Ar-
H), 7.14 (d, J = 7.5 Hz, 2H, Ar-H), 7.54 (d, J = 8.0 Hz, 2H, Ar-
H), 8.02 (m, 1H, Ar-H); 13C NMR (CDCl3, 125 MHz)
d: 19.45,
26.30, 26.33, 26.60, 27.11, 29.33, 32.12, 36.25, 41.13, 50.44,
51.04, 106.06, 112.18, 114.23, 116.65, 116.98, 118.76,
119.98, 121.65, 124.65, 129.09, 127.78, 127.99, 143.58,
146.63, 167.79, 195.38; MS (EI), m/z (%) = 401 (M+, 12), 274
(5), 215 (32); HRMS (EI) Found: M+, 401.2102, C26H27NO3
requires M+, 401.2014; Anal Calcd for C26H27NO3: C, 77.78;
H, 6.78; N, 3.49. Found: C, 77.85; H, 6.84; N, 3.56.
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4.3.7. Methyl 2,7,7-trimethyl-4-(naphthalen-1-yl)-5-oxo-
1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (5n)
0.337 g (89%); pale yellow solid; mp 263–265 8C; IR
(KBr) (
1539, 1438, 789, 747; 1H NMR (CDCl3, 500 MHz)
y
max/cmÀ1): 3523, 3080, 2979, 2879, 1736, 1712,
d
: 0.93 (s,
3H, CH3), 1.12 (s, 3H, CH3), 2.31–2.45 (m, 4H, 2 Â CH2), 2.54
(s, 3H, CH3), 3.72 (s, 3H, OCH3), 5.12 (s, 1H, CH), 6.17 (s, 1H,
NH), 7.38–7.67 (m, 7H, Ar-H); 13C NMR (CDCl3, 125 MHz)
d
: 19.06, 23.32, 25.34, 25.66, 27.67, 28.93, 33.14, 38.28,
47.13, 55.44, 58.98, 108.76, 119.98, 120.76, 121.67, 123.65,
126.89, 128.09, 129.78, 129.99, 139.57, 143.33, 162.72,
192.28; MS (EI), m/z (%) = 326 (M+, 25), 327 (5), 248 (37);
HRMS (EI) Found: M+, 375.1903, C24H25NO3 requires M+,
375.1812; Anal Calcd for C24H25NO3: C, 76.77; H, 6.71; N,
3.73. Found: C, 77.04; H, 6.68; N, 3.80.
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Acknowledgment
The authors are grateful to Payame Noor University for
supporting this work.
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Please cite this article in press as: Poor Heravi MR, et al. One-pot multicomponent synthesis hexahydroquinoline