RSC Advances
Communication
1
3
Hz, 1H, H-8), 7.58 (dd, J7–5 ¼ 2.4 Hz, 1H, H-7), 7.52 (d, 1H, H-5),
C NMR (100 MHz, CDCl
3
) d 197.4, 152.6, 150.1, 137.5,
7
1
6
.06 (dd, 1H, H-3), 2.58 (s, 3H, SCH ).
134.9, 130.0, 129.8, 127.7, 127.4, 121.9, 26.8.
3
1
3
C NMR (100 MHz, CDCl ) d 149.4, 146.4, 137.5, 134.7,
3
29.5, 128.9, 128.7, 122.3, 121.6, 15.6.
29
8
-Hydroxyquinoline (13)
ꢀ
23
Mp ¼ 71 C.
-Aminoquinoline (7)
1
H NMR (400 MHz, CDCl
3
) d 8.78 (dd, J2–3 ¼ 4.4 Hz, J2–4 ¼ 1.6
ꢀ
Mp ¼ 110 C.
Hz, 1H, H-2), 8.15 (dd, J3–4 ¼ 8.4 Hz, 1H, H-4), 7.48–7.41 (m, 2H,
1
H NMR (400 MHz, CDCl
3
) d 8.65 (dd, J2–3 ¼ 4.4 Hz, J2–4 ¼ 1.6
H-3, H-6), 7.33 (d, J3–4 ¼ 8.4 Hz, 1H, H-5), 7.20 (dd, J ¼ 1.2 Hz,
5–7
Hz, 1H, H-2), 7.91 (d, J7–8 ¼ 8.8 Hz, 1H, H-8), 7.90 (dd, J3–4 ¼ 8.4
J6–7 ¼ 7.6 Hz, 1H, H-7).
Hz, 1H, H-4), 7.26 (dd, 1H, H-3), 7.15 (dd, J7–5 ¼ 2.4 Hz, 1H, H-7),
13
3
C NMR (100 MHz, CDCl ) d 152.2, 147.9, 138.2, 136.1,
6
1
2
.89 (d, 1H, H-5), 3.96 (br s, 2H, NH ).
C NMR (100 MHz, CDCl
30.3, 129.8, 121.7, 121.3, 107.3.
1
28.5, 127.7, 121.8, 117.8, 110.1.
1
3
3
) d 146.5, 144.6, 143.1, 133.9,
30
8
-Methoxyquinoline (14)
2
4
1
6
1
-Fluoroquinoline (8)
H NMR (400 MHz, CDCl ) d 8.93 (dd, J ¼ 4.4 Hz, J ¼ 1.6
3
2–3
2–4
Hz, 1H, H-2), 8.13 (dd, J3–4 ¼ 8.4 Hz, 1H, H-4), 7.47 (t, J5–6 ¼ J6–7
H NMR (400 MHz, CDCl ) d 8.87 (d, J2–3 ¼ 4 Hz, 1H, H-2), 8.10–
3
¼
8.0 Hz, 1H, H-6), 7.43 (dd, 1H, H-3), 7.39 (dd, J5–7 ¼ 1.2 Hz,
H, H-5), 7.06 (dd, 1H, H-7), 4.09 (s, 3H, OCH ).
) d 155.1, 149.0, 139.7, 136.3,
8
.07 (m, 2H, H-4, H-8), 7.47 (dd, J7–8 ¼ 8.8 Hz, J ¼ 2.4 Hz, 1H,
7–5
1
3
H-7), 7.42–7.37 (m, 2H, H-3, H-5).
1
3
1
3
C NMR (100 MHz, CDCl
3
C NMR (100 MHz, CDCl
3
) d 160.3 (J ¼ 246.7 Hz), 149.6
1
29.3, 126.9, 121.7, 119.5, 107.7, 56.0.
(
(
J ¼ 2.6 Hz), 145.3, 135.3 (J ¼ 5.4 Hz), 131.9 (J ¼ 9.1 Hz), 128.82
J ¼ 9.9 Hz), 121.7, 119.7 (J ¼ 25.6 Hz), 110.6 (J ¼ 21.4 Hz).
1
9
31
F NMR (376 MHz, CDCl
3
) d 113.3.
8-Thiomethylquinoline (15)
ꢀ
Mp ¼ 76 C.
25
6
-Chloroquinoline (9)
1
H NMR (400 MHz, CDCl
3
) d 8.94 (dd, J2–3 ¼ 4.4 Hz, J2–4 ¼ 1.6
ꢀ
Mp ¼ 38 C.
Hz, 1H, H-2), 8.14 (dd, J3–4 ¼ 8.4 Hz, 1H, H-4), 7.58 (d, J5–6 ¼ 7.6
1
H NMR (400 MHz, CDCl
3
) d 8.90 (dd, J2–3 ¼ 4.0 Hz, J2–4 ¼ 1.6 Hz, 1H, H-5), 7.50 (t, J6–7 ¼ 7.6 Hz, 1H, H-6), 7.44 (dd, 1H, H-3),
Hz, 1H, H-2), 8.07 (dd, J3–4 ¼ 8.4 Hz, 1H, H-4), 8.04 (d, J ¼ 8.8 7.40 (d, 1H, H-7), 2.56 (s, 3H, SCH ).
7–8
3
1
3
Hz, 1H, H-8), 7.80 (d, J5–7 ¼ 2.4 Hz, 1H, H-5), 7.65 (dd, 1H, H-7),
C NMR (100 MHz, CDCl ) d 149.1, 145.3, 139.9, 136.3,
3
7
.42 (dd, 1H, H-3).
128.1, 126.6, 123.5, 122.8, 121.7, 14.3.
1
3
C NMR (100 MHz, CDCl
3
) d 150.6, 146.6, 135.1, 132.3,
131.1, 130.4, 128.8, 126.4, 121.9.
32
8-Aminoquinoline (16)
ꢀ
26
Mp ¼ 63 C.
6-Methylquinoline (10)
1
H NMR (400 MHz, CDCl ) d 8.77 (dd, J ¼ 4.0 Hz, J ¼ 1.6
3
2–3
2–4
1
H NMR (400 MHz, CDCl
3
) d 8.84 (dd, J2–3 ¼ 4.4 Hz, J2–4 ¼ 1.6
Hz, 1H, H-2), 8.06 (dd, J3–4 ¼ 8.4 Hz, 1H, H-4), 7.36 (dd, 1H, H-3),
.34 (t, J5–6 ¼ J6–7 ¼ 7.6 Hz, 1H, H-6), 7.15 (dd, J5–7 ¼ 0.8 Hz, 1H,
H-5), 6.93 (dd, 1H, H-7), 5.00 (br s, 2H, NH ).
Hz, 1H, H-2), 8.06 (d, J3–4 ¼ 8.0 Hz, 1H, H-4), 7.99 (d, J7–8 ¼ 8.4
7
Hz, 1H, H-8), 7.57–7.53 (m, 2H, H-5, H-7), 7.35 (dd, 1H, H-3),
2
2
.53 (s, 3H, CH
3
).
13
C NMR (100 MHz, CDCl
3
) d 147.4, 143.9, 138.4, 135.9,
1
3
C NMR (100 MHz, CDCl ) d 149.4, 146.8, 136.4, 135.4,
3
1
28.8, 127.3, 121.3, 115.9, 109.9.
1
31.7, 129.0, 128.3, 126.5, 121.0, 21.5.
33
27
8-Chloroquinoline (17)
6
-Isopropylquinoline (11)
1
1
H NMR (400 MHz, CDCl
3
) d 9.01 (dd, J2–3 ¼ 4.0 Hz, J2–4 ¼ 1.6
H NMR (400 MHz, CDCl ) d 8.835 (dd, J2–3 ¼ 4.4 Hz, J ¼ 1.6
3
2–4
Hz, 1H, H-2), 8.14 (dd, J3–4 ¼ 8.4 Hz, 1H, H-4), 7.80 (dd, J5–7 ¼ 1.2
Hz, J5–6 ¼ 7.6 Hz, 1H, H-5, H-7), 7.71 (dd, J6–7 ¼ 7.6 Hz, 1H, H-5,
H-7), 7.45–7.41 (m, 2H, H-3, H-6).
Hz, 1H, H-2), 8.05 (d, J3–4 ¼ 8.0 Hz, 1H, H-4), 8.03 (d, J7–8 ¼ 8.8
Hz, 1H, H-8), 7.60 (dd, J7–5 ¼ 2.0 Hz, 1H, H-7), 7.57 (d, 1H, H-5),
7
3
.31 (dd, 1H, H-3), 3.06 (m, 1H, CH), 1.33 (s, 3H, CH ), 1.31
1
3
C NMR (100 MHz, CDCl ) d 150.9, 144.3, 136.4, 133.4,
3
(
s, 3H, CH
3
).
C NMR (100 MHz, CDCl
29.2, 129.1, 128.2, 123.7, 120.9, 33.9, 23.7.
1
3
129.5, 129.4, 126.9, 126.4, 121.8.
3
) d 149.5, 147.1, 147.0, 135.5,
1
6
34
8-Methylquinoline (18)
28
-Acetylquinoline (12)
1
H NMR (400 MHz, CDCl
3
) d 8.95 (dd, J2–3 ¼ 4.0 Hz, J2–4 ¼ 1.6
ꢀ
Mp ¼ 72 C.
Hz, 1H, H-2), 8.13 (dd, J3–4 ¼ 8.0 Hz, 1H, H-4), 7.66 (d, J ¼ 8.0
5–6
1
H NMR (400 MHz, CDCl ) d 9.01 (dd, J ¼ 4.4 Hz, J ¼ 1.6 Hz, 1H, H-5), 7.57 (d, J6–7 ¼ 8.0 Hz, 1H, H-7), 7.43 (t, 1H, H-6),
3
2–3
2–4
Hz, 1H, H-2), 8.45 (d, J5–7 ¼ 1.6 Hz, 1H, H-5), 8.29–8.25 (m, 2H, 7.39 (dd, 1H, H-3), 2.83 (s, 3H, CH ).
3
1
3
H-4, H-7), 8.16 (d, J7–8 ¼ 8.8 Hz, 1H, H-8), 7.35 (dd, J3–4 ¼ 8.4 Hz,
H, H-3), 2.74 (s, 3H, CH ).
C NMR (100 MHz, CDCl
3
) d 149.2, 147.3, 137.0, 136.3,
1
3
129.6, 128.2, 126.3, 125.8, 120.8, 18.1.
21462 | RSC Adv., 2014, 4, 21456–21464
This journal is © The Royal Society of Chemistry 2014