HETEROCYCLES, Vol. 81, No. 4, 2010
941
8.4 Hz, Ar). 13C NMR (CDCl3) = 14.26 (Me), 22.79 (CH2), 23.71 (Me), 30.10, 30.14, 31.53, 31.68
(CH2), 32.96 (Me), 124.03, 125.41, 126.59, 129.57, 129.94, 135.52, 143.94, 147.49, 152.84 (Ar), 206.64
(CO). HRMS: Calcd for C18H23NO; 269.1773. Found; (M+) 269.1737.
3-Acetyl-(4-butylbenzyl)-2-methylquinoline 3d (0.086 g, 0.26 mmol, 87%). Yellow oil. 1H NMR
(CDCl3) = 0.87 (dd, 3H, J = 7.2 Hz and 7.4 Hz, Me), 1.26-1.34 (m, 2H, CH2), 1.51-1.55 (m, 2H, CH2),
2.40 (s, 3H, Me), 2.51 (t, 2H, J = 7. 6 Hz, CH2), 2.68 (s, 3H, Me), 4.32 (s, 2H, CH2), 6.96 (d, 2H, J = 7.8
Hz, Ar), 7.03 (d, 2H, J = 7.8 Hz, Ar), 7.42 (dd, 1H, J = 7.6 Hz and 8.4 Hz, Ar), 7.65 (dd, 1H, J = 7.6 Hz
and 8.4 Hz, Ar), 7.88 (d, 1H, J = 8.4 Hz, Ar), 8.02 (d, 1H, J = 8.4 Hz, Ar). 13C NMR (CDCl3) =
14.16 (Me), 22.55 (CH2), 23.89 (Me), 32.82, 33.78 (CH2), 34.55 (Me), 35.38 (CH2), 124.96, 125.90,
126.82, 128.36, 129.01, 129.57, 129.99, 135.75, 136.71, 140.95, 141.48, 147.84, 153.10 (Ar), 206.78
(CO). HRMS: Calcd for C23H25NO; 331.1936. Found; (M+) 331.1937.
3-Acetyl-4-(3-hydroxylpropyl)-2-methylquinoline 3e (0.069 g, 0.29 mmol, 95%). Pale brown oil. 1H
NMR (CDCl3) = 1.65 (br, 1H, OH), 1.93-1.99 (m, 2H, CH2), 2.62 (s, 3H, Me), 2.65 (s, 3H, Me), 3.05
(dd, 2H, J = 7.4 Hz and 7.6 Hz, CH2), 3.67 (dd, 2H, J = 5.6 Hz and 5.6 Hz, CH2), 7.54 (dd, 1H, J = 7.2
and 7.6 Hz, Ar), 7.70 (dd, 1H, J = 7.2 Hz and 7.6 Hz, Ar), 7.98 (d, 1H, J = 8.4 Hz, Ar), 8.02-8.05 (d, 1H,
J = 8.4 Hz, Ar). 13C NMR (CDCl3) = 23.84 (Me), 26.29, 33.06 (CH2), 33.90 (Me), 61.78 (CH2),
124.16, 125.28, 126.73, 129.67, 130.08, 135.82, 143.05, 147.68, 152.78 (Ar), 207.62 (CO). HRMS:
Calcd for C15H17NO2; 243.1259. Found; (M+) 243.1248.
3-Acetyl-2-methyl-4-neopentylquinoline 3f (0.074 g, 0.29 mmol, 97% yield). Yellow oil. 1H NMR
(CDCl3) = 0.93 (s, 9H, Me) 0.98 (s, 2H, CH2), 2.54 (s, 3H, Me), 2.64 (s, 3H, Me), 7.51 (dd, 1H, J =
7.6 Hz and 8.0 Hz, Ar), 7.69 (dd, 1H, J = 7.2 Hz and 7.6 Hz, Ar), 8.01 (d, 1H, J = 8.4 Hz, Ar), 8.09 (d,
1H, J = 8.4 Hz, Ar). 13C NMR (CDCl3) = 24.30 (Me), 31.21 (3Me), 33.37 (CH2), 34.17 (Me), 41.35
(C(Me)3), 125.74, 125.88, 126.88, 129.41, 129.84, 136.95, 141.99, 147.63, 153.08 (Ar), 206.71 (CO).
HRMS: Calcd for C17H21NO; 255.1623. Found; (M+) 255.1621.
3-Acetyl-4-benzyl-7-chloro-2-methylquinoline 3g (0.056 g, 0.18 mmol, 60%). Yellow granules: mp.
o
1
88-89 C. H NMR (CDCl3) = 2.42 (s, 3H, Me), 2.67 (s, 3H, Me), 4.33 (s, 2H, CH2), 7.04 (d, 2H, J =
7.4 Hz, Ar), 7.20-7.26 (m, 3H, Ar), 7.37 (d, 1H, J = 8.8 Hz, Ar), 7.78 (d, 1H, J = 8.8 Hz, Ar), 8.03 (s, 1H,
Ar). 13C NMR (CDCl3) = 23.92, 32.78 (Me), 34.96 (CH2), 124.29, 126.28, 127.02, 127.80, 128.40,
128.60, 129.08, 135.95, 136.88, 138.28, 140.73, 148.34, 154.56, (Ar), 206.29 (C=O). HRMS: Calcd for
C19H1635ClNO; 309.0920. Found; (M+) 309.0925.
3-Acetyl-4-benzyl-7-methoxy-2-methylquinoline 3h (0.070 g 0.23 mmol, 76%). Yellow amorphous
o
1
solid: mp 132-133 C. H NMR (CDCl3) = 2.39 (s, 3H, Me), 2.65 (s, 3H, Me), 3.94 (s, 3H, OMe),
4.33 (s, 2H, CH2), 7.05 (d, 2H, J = 7.2 Hz, Ar), 7.08 (d, 1H, J = 9.2 Hz, Ar), 7.18-7.25 (m, 3H, Ar), 7.37
(s, 1H, Ar), 7.75 (d, 1H, J = 9.2 Hz, Ar). 13C NMR (CDCl3) = 22.60, 31.67 (Me), 33.62 (CH2),
55.49 (OMe), 106.34, 118.59, 119.59, 124.76, 125.55, 127.20, 127.69, 133.61, 137.47, 139.50, 148.49,
152.23, 159.87 (Ar), 205.65 (C=O). HRMS: Calcd for C20H19NO2; 305.1416. Found; (M+) 305.1408.
3-Acetyl-4-benzyl-2,6-dimethylquinoline 3i (0.058 g 0.20 mmol) in 67% yield. Yellow granules: mp
o
1
123-124 C. H NMR (CDCl3) = 2.37 (s, 3H, Me), 2.44 (s, 3H, Me), 2.65 (s, 3H, Me), 4.34 (s, 2H,
CH2), 7.06 (d, 2H, J = 7.2 Hz, Ar), 7.18-7.26 (m, 3H, Ar), 7.49 (d, 1H, J = 8.4 Hz, Ar), 7.64 (s, 1H, Ar),
7.92 (d, 1H, J = 8.4 Hz, Ar). 13C NMR (CDCl3) = 22.13, 23.75, 32.78 (Me), 34.70 (CH2), 123.68,
123.70, 125.83, 126.80, 128.49, 128.95, 129.29, 132.28, 136.73, 138.72, 139..90, 146.42, 152.00 (Ar),
206.97 (C=O). HRMS: Calcd for C20H19NO; 289.1467. Found; (M+) 289.1467.
9-Hexyl-5,6,7,8-tetrahydroacridine 3j (0.055 g, 0.20 mmol, 68%). Yellow oil. 1H NMR (CDCl3) =
0.90 (dd, 3H, J = 6.8 Hz and 6.8 Hz, Me), 1.32-1.48 (m, 4H, CH2), 1.48 (dt, 2H, J = 6.8 Hz and 7.0 Hz,
CH2), 1.56 (dt, 2H, J = 6.8 Hz and 8.0 Hz, CH2), 1.93-1.98 (m, 4H, CH2), 2.92 (dd, 2H, J = 7.6 Hz and
8.0 Hz, CH2), 3.11 (dd, 2H, J = 6.0 Hz and 6.2 Hz, CH2), 7.43 (dd, 1H, J = 7.6 Hz and 8.0 Hz, Ar), 7.57
(dd, 1H, J = 7.6 Hz and 8.4 Hz, Ar), 7.93 (d, 1H, J = 8.0 Hz, Ar), 7.96 (d, 1H, J = 8.4 Hz, Ar). 13C NMR
(CDCl3) = 14.33 (Me), 22.90, 23.04, 23.46, 26.57, 27.90, 29.84, 30.24, 31.91, 34.74 (CH2), 123.54,
125.47, 126.41, 128.22, 128.25, 129.33, 145.94, 146.55, 159.04 (Ar). HRMS: Calcd for C19H25N;
267.1987. Found; (M+) 267.1989.