PASHKOVSKII et al.
862
1
3
1715. H NMR spectrum (CD3CO2D), δ, ppm:
1.67 sext (1H, thiophene, J = 6.5 Hz), 1.87–1.95 m
(1H, thiophene), 1.99 sext (1H, thiophene, J = 6.0 Hz),
2.07 sext (1H, thiophene, J = 6.0 Hz), 2.46 d (2H,
C4H7SCH2, J = 7.5 Hz), 2.76–2.81 m (1H, thiophene),
2.86–2.91 m (1H, thiophene), 3.62 quint (1H, CHS,
J = 7.0 Hz), 4.68 s (2H, 5-H). 13C NMR spectrum
(CD3CO2D), δC, ppm: 29.70 (CH2), 30.81 (CH2), 32.93
(CH2), 37.28 (CH2), 48.11 (CH), 68.42 (C5), 100.71
(Cquat), 176.01 (C=O), 179.02 (C=O). Found, %:
C 53.52; H 6.15. C9H12O3S. Calculated, %: C 53.98;
H 6.04.
8.5 Hz), 7.31 d (2H, Harom, J = 8.5 Hz). 13C NMR
spectrum (CD3CO2D), δC, ppm: 25.17 (CH2), 68.56
(C5), 99.97 (Cquat), 127.79 (CH=), 128.45 (2C, CHarom),
129.51 (2C, CHarom), 130.59 (CH=), 133.41 (Cquat),
137.23 (Cquat), 175.62 (C=O), 178.84 (C=O). Found,
%: C 62.38; H 4.39. C13H11ClO3. Calculated, %:
C 62.29; H 4.42.
3-[3-(4-Fluorophenyl)propyl]tetrahydrofuran-
2,4-dione (VIIb). Yield 37% (a), mp 104–107°C. IR
spectrum, ν, cm–1: 1515, 1590–1670 br, 1720. 1H NMR
spectrum (CDCl3), δ, ppm: 1.79 quint (2H, CH2CH2-
3
3
CH2, J = 7.5 Hz), 2.24 t (2H, 3-CH2, J = 7.5 Hz),
3
3-[(E)-3-(4-Fluorophenyl)prop-2-en-1-yl]tetra-
hydrofuran-2,4-dione (VIb). Yield 80% (b), mp 156–
158°C. IR spectrum, ν, cm–1: 1450, 1550 sh, 1580–
1665 br, 1715. H NMR spectrum (pyridine-d5), δ,
ppm: 3.35 d (2H, 3-CH2, J = 6.0 Hz), 4.80 s (2H,
2.58 t (2H, C6H4CH2, J = 7.5 Hz), 4.64 s (2H, 5-H),
3
3
6.92 t (2H, 3′-H, 5′-H, JHH ≈ JHF = 8.5 Hz), 7.10 d.d
3
4
(2H, 2′-H, 6′-H, JHH = 8.5, JHF = 6.0 Hz), 10.65 br.s
(1H, OH, enol). 13C NMR spectrum (CDCl3), δC, ppm:
20.77 (CH2), 29.42 (CH2), 34.71 (CH2), 67.78 (C5),
100.94 (Cquat), 114.88 and 115.05 (C3′, C5′), 129.64 and
129.70 (C2′, C6′), 137.60 (Cquat), 160.23 and 162.17
(C–F), 174.42 (C=O), 174.63 (C=O). Found, %:
C 65.89; H 5.58. C13H13FO3. Calculated, %: C 66.09;
H 5.55.
1
3
3
5-H), 6.46 d.t (1H, CH2CH=CH, J = 16.0, 6.0 Hz),
6.57 d (1H, CH2CH=CH, 3Jtrans = 16.0 Hz), 7.06 t (2H,
3
3
3′-H, 5′-H, JHH ≈ JHF = 8.5 Hz), 7.32 d.d (2H, 2′-H,
6′-H, JHH = 8.5, JHF = 5.5 Hz). 13C NMR spectrum
(pyridine-d5), δC, ppm: 25.64 (CH2), 67.71 (C5), 97.67
(Cquat), 115.54 and 115.71 (C3′, C5′), 127.62 (CH=),
128.12 and 128.18 (C2′, C6′), 129.44 (CH=), 134.47
(Cquat), 161.29 and 163.23 (C–F), 175.58 (C=O),
176.03 (C=O). Found, %: C 66.41; H 4.68. C13H11FO3.
Calculated, %: C 66.66; H 4.73.
3
4
REFERENCES
1. Akhrem, A.A., Lakhvich, F.A., Lis, L.G., Khripach, V.A.,
Fil’chenkov, N.A., Kozinets, V.A., and Pashkovskii, F.S.,
Dokl. Akad. Nauk SSSR, 1990, vol. 311, p. 1381.
3-[(E)-3-(4-Nitrophenyl)prop-2-en-1-yl]tetra-
hydrofuran-2,4-dione (VIc). Yield 73 (a), 83% (b);
mp 178–181°C. IR spectrum, ν, cm–1: 1400, 1445,
2. Pashkovsky, F.S., Lokot, I.P., and Lakhvich, F.A., Synlett,
2001, p. 1391.
3. Pashkovskii, F.S., Shchukina, E.M., Gribovskii, M.G.,
and Lakhvich, F.A., Russ. J. Org. Chem., 2008, vol. 44,
p. 657.
4. Zimmer, H., Hillstrom, W.W., Schmidt, J.C., See-
muth, P.D., and Vogeli, R., J. Org. Chem., 1978, vol. 43,
p. 1541; Schmidt, D.G. and Zimmer, H., J. Heterocycl.
Chem., 1983, vol. 20, p. 787.
5. Effenberger, F. and Syed, J., Tetrahedron: Asymmetry,
1998, vol. 9, p. 817; Chrusciel, R.A., Maggiora, L.L.,
Thaisrivongs, S., Tustin, J.M., Smith, C.W., Tom-
masi, R.A., Aristoff, P.A., Skulnick, H.I., Howe, W.J., and
Bundy, G.L., PCT Int. Appl. WO 9507901, 1995; Chem.
Abstr., 1995, vol. 123, no. 55683p.
6. Ramachary, D.B. and Barbas, C.F., III, Chem. Eur. J.,
2004, vol. 10, p. 5323; Simon, C., Constantieux, T., and
Rodrigues, J., Eur. J. Org. Chem., 2004, p. 4957; Koz-
lov, N.G., Tarasevich, V.A., Vasilevskii, D.A., and Basa-
laeva, L.I., Russ. J. Org. Chem., 2006, vol. 42, p. 107;
Kozlov, N.G., Gusak, K.N., and Skatetskii, V.V., Russ. J.
Org. Chem., 2006, vol. 42, p. 112.
1
1525, 1595, 1655 br, 1720. H NMR spectrum
(pyridine-d5), δ, ppm: 3.38 d (2H, 3-CH2, 3J = 6.0 Hz),
3
4.83 s (2H, 5-H), 6.62 d (1H, CH2CH=CH, Jtrans
16.0 Hz), 6.71 d.t (1H, CH2CH=CH, J = 16.0,
=
3
3
6.0 Hz), 7.43 d (2H, Harom, J = 8.5 Hz), 8.15 d (2H,
Harom, J = 8.5 Hz). 13C NMR spectrum (pyridine-d5),
3
δC, ppm: 25.85 (CH2), 67.73 (C5), 97.09 (Cquat), 124.19
(2C, CHarom), 127.02 (2C, CHarom), 128.96 (CH=),
133.17 (CH=), 144.59 (Cquat), 146.83 (Cquat), 175.80
(2C, C=O). Found, %: C 59.74; H 4.33. C13H11NO5.
Calculated, %: C 59.77; H 4.24.
3-[(E)-3-(4-Chlorophenyl)prop-2-en-1-yl]tetra-
hydrofuran-2,4-dione (VId). Yield 71% (b), mp 135–
137°C. IR spectrum, ν, cm–1: 1490, 1550 sh, 1645 br,
1715. H NMR spectrum (CD3CO2D), δ, ppm: 3.10 d
(2H, 3-CH2, J = 6.5 Hz), 4.71 s (2H, 5-H), 6.26 d.t
1
3
3
(1H, CH2CH=CH, J = 15.5, 6.5 Hz), 6.42 d (1H,
CH2CH=CH, Jtrans = 15.5 Hz), 7.25 d (2H, Harom, 3J =
3
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 6 2009