1
078
S. M. Agamy et al. • Enaminones as Building Blocks in Heterocyclic Synthesis
9
.11 (s, 1H, coumarin 4-H). - MS: m /z = 309
(309.31): calcd.
69.89, v = 3423 (NH), 1658 cm
DMSO): d = 3.68 (s, 3H, OCH3), 5.34 (s, 1H,
M.p. 210° C (EtO H ); yield 2.96 g (75%). - IR:
(C =0). - XH NM R (d6-
[
M+].
-
C
1 8
H
1 5 N 0
4
C
' 1
H 4.89, N 4.53; found C 69.91, H 4.82, N 4.34.
4
2
7
-H), 6.82 (d, 2H, 7 = 8 Hz, arom. H), 7.09 (s, 2H,
-H, -H), 7.24 (d, 2H, J = Hz, arom. H), 7.43-
.51 (m, 10H, arom. H), 9.23 (s, 1H, NH). - MS:
(395.44): calcd.
6
8
Ethyl 2-methyl-6-(2-pyridyl)pyridine-3-carboxylate
(
16b)
m/z = 395 [M+]. -
C
2 6
H
2 1 N 0
3
C 78.96, H 5.35, N 3.54; found C 78.73, H 5.31,
N 3.57.
M.p. 80° C (EtO H ); yield 2.10 g (
v = 1718 cm (C = 0). - XH NM R (d
5 = 1.41 (t, 3H, 7 = 8 Hz, CH3), 2.91 (s, 3H, CH 3),
.38 (q, 2H, 7 = Hz, O CH 2), 7.30-7.33 (m, 1H,
pyridyl 5'-H ), 7.49 (m, 1H, pyridyl 4'-H ), 8.27-
8
6
%). - IR:
"
1
6
-DMSO):
(
4
3
,5-Dibenzoyl-4-(4-methoxyphenyl)pyridine (18)
8
Compound 15 (3.95 g, 10 mmol) was heated un-
der reflux for
conc. H N 0
2.5 ml) following the procedure described for oxi-
1
h, in a mixture of water ( 1
0
ml)
8
8
.32 (m, 2H, pyridyl 3'-H , 5-H), 8.48 (d, 1H, J =
Hz, 4-H), 8.67 (d, 1H, J = Hz, pyridyl '-H). -
(242.27):
3
(d = 1.42, 3 ml) and conc. H
2
S 0
4
8
6
(
MS: m/z = 242 [M+].
-
C
1 4
H
1 4
N
2
0
2
dation of diethyl l,4-dihydro-2,6-dimethylpyri-
dine-3,5-dicarboxylate [16] The reaction mixture
was allowed to assume room temperature. The
solid product, so obtained was filtered off and
crystallized from ethanol.
calcd. C 69.40, H 5.83, N 11.56; found C 69.29,
H 5.76, N 11.61.
3
1
,5-Dibenzoyl-4-(4-methoxyphenyl)-
,4-dihydropyridine (17)
M.p. 92° C (EtO H ); yield 3.37 g (
8
6
%). - IR:
-DMSO):
v = 1664 cm (C = 0). - XH NMR (d
“
1
6
To a stirred suspension of compound 2a (1.75 g, <5 = 3.52 (s, 3H, O C H 3), 6.60-6.62 (m, 2H, arom.
1
0
mmol) and ammonium acetate ( 1 g), acetic acid
H), 6.93-6.95 (m, 2H, arom. H), 7.38-7.41 (m,
4H, arom. H), 7.53-7.57 (m, 2H, arom. H), 7.65-
(
10 ml), anisaldehyde (1.36 g, 10 mmol) was
added. The reaction mixture was heated under re- 7.67 (m, 4H, arom. H ), 8.83 (s, 2H, 2-H,
6
-H). -
flux for 5h, then allowed to cool to room tem per- MS: m/z = 393 [M+]. - C2 6
H
1 9 N 0
3
(395.46): calcd.
ature. The solid product so obtained was filtered
off, and crystallized from ethanol.
C 79.37, H 4.87, N 3.56; found C 79.45, H 4.86,
N 3.56.
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