HETEROCYCLIC ANALOGS OF PROSTAGLANDINS: II.
237
3
1.46 d (3H, CH3CH11, J 6.0 Hz), 1.502.11 m [4H,
(1H, H8), 2.803.00 d.d (2.90 d.d) (1H, Ha14, 2J 17.0,
3J 7.0 Hz), 3.283.45 d.d.d (3.37 d.d.d) (1H, H12, 3J 10.0,
9.0, 8.0 Hz), 3.413.61 d.d (3.51 d.d) (1H, Hb14, 2J 17.0,
3J 11.0 Hz), 3.67 s (3H, CO2CH3), 4.14 2 d.d (1H, Ha11 in
lacton ring, 2J 9.0, 3J 9.0 Hz), 4.49 d.d (1H, Hb11 in lacton
ring, 2J 9.0, 3J 8.0 Hz), 5.68 br.d.d (1H, CHPy, 3J 11.0,
(CH2)2CH2Ar], 2.60 br.t (2H, CH2Ar, 3J 7.0 Hz), 2.72 t
(2H, isoxazolyl-CH2, 3J 7.5 Hz), 2.873.00 m (1H, H12),
3.07 d.d (1H, H8, 3J 12.0, 9.5 Hz), 3.10 t (2H, CH2CO2Et,
3J 7.5 Hz), 3.80 s (3H, OCH3), 4.20 q (2H, CO2CH2CH3,
3J 7.0 Hz), 4.47 d.q (1H, CH3CH11, 3J 9.5, 6.0 Hz),
5.94 s (1Hisoxazole), 6.686.82 m (3Harom), 7.22 br.t
(1Harom, J 7.5 Hz). Mass spectrum: m/z 415 [M]+.
Found, %: C 66.54; H 6.98. C23H29NO6. Calculated,
%: C 66.49; H 7.04.
3
7.0 Hz), 7.26 d (2HPy, J 5.0 Hz), 8.63 br.d (2HPy,
3J 5.0 Hz). Mass spectrum: m/z 374 [M]+. Found, %:
C 64.23; H 6.94. C20H26N2O5. Calculated, %: C 64.15;
H 7.00.
3
Methyl 7-{5a-methyl-2-oxo-4b-[5a,b-(pyridin-
4-yl)-4,5-dihydroisoxazol-3-yl]tetrahydrofuran-3a-
yl}heptanoate (XXVIIa, b). Yield 80%. IR spectrum,
Methyl 4-{3-(2-oxo-4b-[5a,b-(pyridin-4-yl)-4,5-
dihydroisoxazol-3-yl]tetrahydrofuran-3a-yl)propyl}-
benzoate (XXIVa, b). Yield 80%. IR spectrum, cm :
1010, 1030, 1050 sh, 1060, 1120, 1175, 1185, 1205, 1260,
1290, 1320, 1345, 1390, 1445, 1495, 1550, 1620, 1640,
1725, 1775. 1H NMR spectrum, d, ppm: 1.562.00 m [4H,
(CH2)2CH2Ar], 2.602.90 m (4H, H8 + Ha14 + CH2Ar),
3.233.47 m (2H, H12 + Hb14), 3.90 s (3H, CO2CH3),
1
1
cm : 1000, 1030, 1080, 1120, 1190, 1225 sh, 1240 sh,
1270, 1320, 1350, 1395, 1420, 1450, 1470, 1610, 1745,
1
1785 max H NMR spectrum, d, ppm: 1.121.40 m (6H,
3CH2 a-chain), 1.44 d, 1.48 d (3H, CH3CH11, 3J 6.0 Hz),
1.521.70 m (3H, 1H from CH2 at the ring +
CH2CH2CO2Me), 1.721.91 m (1H from CH2 at the
ring), 2.30 2 t (2H, CH2CO2Me, 3J 7.0 Hz), 2.633.00 m
2
3
4.11 2 d.d (1H, Ha11 in lacton ring, J 9.0, J 9.0 Hz),
4.48 br.d.d (1H, Hb11 in lacton ring, J 9.0, J 8.0 Hz),
2
3
2
(3H, H8 + H12 + Ha14), 3.50 2 d.d (1H, Hb14, J 17.0,
5.64 br.d.d (1H, CHPy, 3J 11.0, 7.0 Hz), 7.22 narrow m
3J 11.0 Hz), 3.68 s (3H, CO2CH3), 4.38 2 d.q (1H,
CH3CH11, 3J 9.0, 6.0 Hz), 5.68 2 d.d (1H, CHPs, 3J 11.0,
7.0 Hz), 7.26 d (2HPy, 3J 5.0 Hz), 8.64 narrow m (2HPy).
Mass spectrum: m/z 388 [M]+. Found, %: C 64.84;
H 7.24. C21H28N2O5. Calculated, %: C 64.93; H 7.27.
3
(4H, 2HPh + 2HPy), 7.96 br.d (2HPh, J 7.5 Hz),
8.60 narrow m (2HPy). Mass spectrum: m/z 408 [M]+.
Found, %: C 67.52; H 5.89. C23H24N2O5. Calculated, %:
C 67.63; H 5.92.
Methyl
4-{3-(5a-methyl-2-oxo-4b-[5a,b-
The study was carried out under a financial support
of the Foundation for Basic Research of Belarus Republic
(grant X01-121).
(pyridin-4-yl)-4,5-dihydroisoxazol-3-yl]tetra-
hydrofuran-3a-yl)propyl}benzoate (XXVa, XXVb).
Yield 82%. IR spectrum, cm : 1030, 1055 sh, 1080, 1120,
1190, 1240, 1290 max, 1315, 1350, 1395, 1420, 1440, 1610,
1
REFERENCES
1
1725, 1785. H NMR spectrum, d, ppm: 1.43 d, 1.46 d
1. Pashkovskii, F.S., Katok, Ya.M., Khlebnikova, T.S., Korole-
va, E.V., and Lakhvich, F.A., Zh. Org. Khim., 2003, vol. 39,
p. 1060.
2. Rashkovsky, F.S., Katok, Ya.M., Khlebnicova, T.S., and
Lakhvich, F.A., Tetrahedron Lett., 2001, vol. 42, p. 3657.
3. Pashkovskii, F.S., Shchukina, E.M., and Lakhvich, F.A.,
Vestsi NANB, Ser Khim., 2002, no. 4, p. 67.
4. Akhrem, A.A., Lakhvich, F.A., Khripach, V.A., Antone-
vich, I.P., Pap, A.A., and Lis, L.G., Zh. Org. Khim., 1981,
vol. 17, p. 2242.
(3H, CH3CH11, 3J 6.0 Hz), 1.581.96 m [4H,
3
(CH2)2CH2Ar], 2.66 t, 2.69 t (2H, CH2Ar, J 7.5 Hz),
2.712.97 m (3H, H8 + H12 + Ha14), 3.42 2d.d (1H, Hb14,
3
2J 17.0, J 11.0 Hz), 3.90 s (3H, CO2CH3), 4.37 2 d.q
(1H, CH3CH11, 3J 9.0, 6.0 Hz), 5.64 br.d.d (1H, CHPy,
3J 11.0, 7.0 Hz), 7.22 narrow m (4H, 2HPh + 2HPy),
7.96 2 d (2HPh, 3J 8.0 Hz), 8.60 narrow m (2HPy). Mass
spectrum: m/z 422 [M]+. Found, %: C 68.33; H 6.18.
C24H26N2O5. Calculated, %: C 68.23; H 6.20.
5. Gilbert,A.M.,Miller,R.,andWulff,W.D., Tetrahedron, 1999,
vol. 55, p. 1607.
Methyl 7-{2-oxo-4b-[5a,b-(pyridin-4-yl)-4,5-di-
hydroisoxazol-3-yl]tetrahydrofuran-3a-yl}-heptano-
ate (XXVIa, b). Yield 85%. IR spectrum, cm : 1000,
1030, 1080, 1120, 1190, 1225 sh, 1240 sh, 1270, 1320,
1350, 1395, 1420, 1450, 1470, 1610, 1745, 1785 max
1H NMR spectrum, d, ppm: 1.121.50 m (6H, 3CH2
a-chain), 1.501.71 m (3H, 1H from CH2 at the ring +
CH2CH2CO2Me), 1.711.92 m (1H from CH2 at the
ring), 2.31 t (2H, CH2CO2Me, 3J 7.5 Hz), 2.622.80 m
6. Jaworsky, T., Kolodzejek, W., Prejzner, J., and Wlostow-
sky, M., Pol. J. Chem., 1981, vol. 55, p. 1321. ,
7. Pashkovsky, F.S., Lakhvich, F.A., Ricci, A., and Comes-
Franchini, M., Mendeleev Commun., 2001, vol. 11, p. 101.
8. Gunther, C. and Mosandl, A. Lieb. Ann., 1986, p. 2112.
9. Lakhvich, F.A., Koroleva, E.V., and Akhrem, A.A., Khim.
Geterotsikl. Soedin., 1989, 435; Baranski,A., Cholewka, E.,
Pol. J. Chem., 1987, vol. 61, p. 631.
1
10. Koroleva, E.V., Katok, Ya.M., Chernikhova, T.V., and
Lakhvich, F.A., Khim. Geterotsikl. Soedin., 1999, p. 252.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 42 No. 2 2006