HETEROCYCLES, Vol. 77, No. 2, 2009
1169
6
8
5
7
6
.32-6.72 (2H, m, C and C -H), 6.78-7.11 (2H, m, C and C -H).
1
Quinoline : Eluted with hexane - EtOAc (2:1). Yellow oil. H-NMR (CDCl
3
), δ : 7.38 (1H, dd, J = 8.3 Hz,
3
5
6
7
4
8
4
.2 Hz, C -H), 7.45-7.90 (3H, m, C , C , and C -H), 8.13 (2H, d, J = 8.3 Hz, C and C -H), 8.90 (1H, dd, J
2
=
4.2 Hz, 1.4 Hz, C -H).
1
0
2
1
(1H)-Quinolinone : Eluted with EtOAc-EtOH (20:1). White solids. Mp 199.5-200.5 °C (lit.,
1
3
6
96-197 °C). H-NMR (CDCl
3
), δ : 6.72 (1H, d, J = 9.5 Hz, C -H), 7.02-7.32 (1H, m, C -H), 7.32-7.68
5
7
8
4
(
3H, m, C , C , and C -H), 7.81 (1H, d, J = 9.5 Hz, C -H), 12.50 (1H, brs, NH).
11
Nicotinic acid : Eluted with EtOAc-EtOH (4:1). Yellow solids. Mp 237.7-239.1 °C (lit., 236-239 °C).
1
5
4
6
H-NMR (DMSO-d ), δ : 7.50 (1H, dd, J = 7.6 Hz, 4.7 Hz, C -H), 8.25 (1H, d, J = 7.6 Hz, C -H), 8.74
6
2
(
1H, d, J = 4.7 Hz, C -H), 9.08 (1H, s, C -H).
1
Ethyl nicotinate : Eluted with hexane - EtOAc (1:1). Pale yellow liquids. H-NMR (CDCl ), δ : 1.41 (3H,
3
5
t, J = 7.1 Hz, CH
3
), 4.42 (2H, q, J = 7.1 Hz, CH
2
), 7.38 (1H, dd, J = 7.9 Hz, 4.8 Hz, C -H), 8.29 (1H, dt, J
4
6
2
=
7.9 Hz, 1.7 Hz, C -H), 8.76 (1H, dd, J = 4.8 Hz, 1.7 Hz, C -H), 9.22 (1H, d, J = 1.7 Hz, C -H).
1
2
1
3
-Diethylaminopyridine : Eluted with hexane - EtOAc (15:1). Slight violet liquids. H-NMR (CDCl ), δ :
3
5
.18 (6H, t, J=7.0 Hz, CH
3
x 2), 3.51 (4H, q, J=7.0 Hz, CH
2
x 2), 6.32-6.57 (2H, m, C and C -H), 7.38
4
6
(
1H, td, J=7.8 Hz, 1.9 Hz, C -H), 8.13 (1H, dd, J=5.5 Hz, 1.9 Hz, C -H).
1
N,N-Diethyl-4-quinolinecarboxamide : Eluted with EtOAc. White oil. H-NMR (CDCl
3
), δ : 1.02 (3H, t, J
=
7.1 Hz, CH
3
), 1.38 (3H, t, J = 7.1 Hz, CH
3
), 3.09 (2H, q, J = 7.1 Hz, CH
2
), 3.43-3.95 (2H, m, CH
2
), 7.29
3
5
6
7
8
(
1H, d, J = 4.4 Hz, C -H), 7.41-7.90 (3H, m, C , C , and C -H), 8.14 (1H, dd, J = 8.4 Hz, 1.5 Hz, C -H),
2
8
7
.94 (1H, d, J = 4.4 Hz, C -H).
1
3
-Chloroquinoline : Eluted with hexane - EtOAc (2:1). Yellow liquids. H-NMR (CDCl ), δ : 7.25-7.60
3
6
5
4
8
(
2H, m, C and C -H), 7.74 (1H, d, J = 8.8 Hz, C -H), 7.95-8.24 (2H, m, C and C -H), 8.90 (1H, dd, J =
2
4
1
7
8
.2 Hz, 1.6 Hz, C -H).
-Phenyl-1H-pyrazolo[3,4-d]pyrimidine : Eluted with hexane - EtOAc (2:1). Pale yellow solids. Mp
1
2
1
5-79 °C (lit., 80 °C). H-NMR (CDCl
3
), δ : 7.25-7.70 (3H, m, phenyl-H), 8.08-8.38 (2H, m, phenyl-H),
3
6
4
.32 (1H, s, C -H), 9.12 (1H, s, C -H), 9.26 (1H, s, C -H).
13
1
Quinoxaline : Eluted with hexane - EtOAc (2:1). Brown needles. Mp 28.5 °C (lit., 29-30 °C). H-NMR
5
8
6
7
2
3
(
3
CDCl ), δ : 7.66-7.91 (2H, m, C and C -H), 7.91-8.22 (2H, m, C and C -H), 8.85 (2H, s, C and C -H).
The reaction of iodoheterocycles with In in the presence of pivalaldehyde (General procedure 2) : A
mixture of iodoheterocycles, In, and excess pivalaldehyde was heated to reflux. The reaction mixture was
diluted with EtOAc, and insoluble solids were filtered off. After the filtrate was diluted with water, the
mixture was neutralized with 1 N NaOH and extracted with EtOAc. The organic layer was dried over
Na SO and treated with silica gel column chromatography to give the corresponding product.
2
4