REACTION OF VINYLPYRIDINES AND VINYLQUINOLINES
1741
IVa and IVb in PPAa.
C H N . Calculated, %: C 78.23; H 6.57; N 15.20.
12
12
2
We showed that at heating compound I with triazines
IVa and IVb in PPAformed 2,3'-bipyridyls Xa and Xb in
3,4'-Bipyridyl (XI). Yield 0.064 g (41%) (from
compound II), 0.055 g (35%) (from compound XIV).
3
7 and 34% yield respectively. Similarly from azine II
Yellow oily substance. Picrate, mp 205–206°C (mp 204–
205°C [5]). H NMR spectrum, δ, ppm: 7.41 d.d (1H,
1
formed bipyridyl XI, from reagent III, compound XII.
5
3'
5'
H , J 7.9, J 4.9 Hz), 7.49 d (2H, H , H , J 4.9 Hz),
Instead of compounds I–III their precursors, alcohols
XIII–XV, can be employed.
4,5
5',6'
3
4
7
.74 d (1H, H , J 7.9 Hz), 7.91 d.d (1H, H , J 7.9,
3,4
4,5
J2 2.1 Hz), 8.67 d (1H, H , J 4.9 Hz), 8.70 d (2H, H2',
6
,4
5,6
2'
General procedure. A mixture of 1 mmol of
vinylhetarene I–III or alcohol XIII–XV and 3–4 g of
PPA was vigorously stirred for 15 min at 60–65°C,
6
'
H , J 4.9 Hz), 8.88 d (1H, H , J 2.1 Hz). Found, %:
2
',4'
C 77.06; H 5.09; N 17.85. C H N . Calculated, %: C 76.90;
10 8 2
H 5.16; N 17.94.
-(3-Pyridyl)quinoline (XII). Yield 0.116 g (56%)
from compound III), 0.117 g (57%) (from compound
1
.5 mmol of an appropriate 1,3,5-triazine was added, and
the reaction mixture was stirred for 2 h at 70–75°C, then
h at 120–130°C. The reaction mixture was cooled,
2
(
5
XV), mp 69–71°C (from petroleum ether) (mp 70–71°C
poured at stirring into 30 ml of cold water, alkalinized
with 25% aqueous ammonia, saturated with potassium
carbonate, and extracted with ethyl acetate (5×50 ml).
The solvent was evaporated, the residue was subjected
to column chromatography. Eluent ethyl acetate–
petroleum ether, 1:1.
1
[
5]). H NMR spectrum corresponds to the published
one [6]. Found, %: C 81.28; H 4.71; N 13.53. C H N .
14 10
2
Calculated, %: C 81.53; H 4.89; N 13.58.
NMR spectra were registered on a spectrometer
Bruker WP-200 (200 MHz) in CDCl , internal reference
3
TMS. The reactions progress was monitored and the
homogeneity of compounds obtained was cheched by
TLC on Silufol UV-254 plates, eluent ethyl acetate–
petroleum ether, 1:1.
2
,3'-Bipyridyl (Xa). Yield 0.058 g (37%) ([from
compound I), 0.056 g (from compound XIII). Yellow
oily substance. Picrate, mp 153–154°C (mp 153–155°C
5]). H NMR spectrum, δ, ppm: 7.27 d.d (1H, H , J
.9, J5',6' 4.9 Hz), 7.39 d.d (1H, H , J 7.9, J 4.9 Hz),
.74 d (1H, H , J 7.9 Hz), 7.78 t (1H, H J 7.9 Hz),
.31 d.d (1H, H , J
1H, H , J5 4.9 Hz), 8.72 d (1H, H , J
.18 d (1H, H , J
1
5'
[
4
',5'
5
7
7
8
(
9
4,5
5,6
3
4
REFERENCES
3
4
,4
'
7.9, J2',4' 2.1 Hz), 8.64 d
4.9 Hz),
2.1 Hz). Found, %: C 77.08;
4
',5'
1. Aksenov, A.V., Borovlev, I.V., Aksenova, I.V., and Kova-
6
6'
,6
5',6'
lev, D.A., Khim. Geterotsikl. Soedin., 2007, p. 1590.
2
'
2
',4'
2
. Aksenov, A.V., Borovlev, I.V., Aksenova, I.V., Pisaren-
ko, S.V., and Kovalev, D.A., Tetrahedron Lett., 2008, vol. 49,
p. 707.
H 5.11; N 17.81. C H N . Calculated, %: C 76.90; H 5.16;
N 17.94.
10 8 2
2
',6'-Dimethyl-2,3'-bipyridyl (Xb). Yield 0.063 g
3
. Borovlev, I.V.,Aksenov,A.V.,Aksenova, I.V., and Pisaren-
ko, S.V., Izv. Akad. Nauk, Ser Khim., 2007, p. 2275.
4. Uhlig, F., Angew. Chem., 1954, vol. 66, p. 435.
5. Yamamoto, Y., Azuma, Y., and Mitoh, H., Synthesis, 1986,
p. 564.
(
34%). Yellow oily substance. Picrate, mp 136–138°C
H NMR spectrum, δ, ppm: 2.42 s (3H, Me), 2.46 s (3H,
Me), 7.27 d (1H, H , J
J4,5 7.9, J 4.9 Hz), 7.54 d (1H, H , J 7.9 Hz), 7.59 t
1H, H , J 7.9 Hz), 8.21 d (1H, H , J 7.9 Hz), 8.89 d
4',5'
1H, H , J 4.9 Hz). Found, %: C 78.39; H 6.49; N 15.12.
1
5
'
5
7.9 Hz), 7.39 d.d (1H, H ,
4
',5'
3
5,6
3,4
4
4'
6. Ishikura, M., Oda, I., and Terashima, M., Heterocycles, 1985,
vol. 23, p. 2375.
(
(
6
5,6
a
PPA used contained 86% of P O and was prepared by procedure [4].
2
5
RUSSIAN JOURNAL OF ORGANIC CHEMISTRYVol. 45 No. 11 2009