1436
KUKHAREV et al.
Table 3. 1H NMR spectra of vinyloxyalkylamides IIa IId and IIIa IIId
Comp.
no.
Chemical shifts , ppm (J, Hz)
3
3
3
2
IIa
IIb
3.62 d.t (4H, NCH2, J = 5.2, JCH, NH = 5.6), 3.77 t (4H, OCH2, J = 5.2), 4.05 d.d (2H, cis-H, J = 2.3,
3Jcis = 6.8), 4.15 d.d (2H, trans-H, J = 2.3, Jtrans = 14.3), 6.44 d.d (2H, OCH, Jcis = 6.8, Jtrans
14.3), 7.81 br.s (2H, NH)
=
2
3
3
3
3
3
3
1.92 m (4H, CH2CH2CH2), 3.44 d.t (4H, NCH2, J = 5.7, JCH, NH = 6.4), 3.74 t (4H, OCH2, J = 5.7), (2H,
cis-H, J = 1.8, Jcis = 6.8), 4.17 d.d (2H, trans-H, J = 1.8, Jtrans = 14.4), 6.44 d.d (2H, OCH, 3Jcis = 6.8,
2
3
2
3
3Jtrans = 14.4), 7.71 br.s (2H, NH)
3
3
3
IIc
IId
1.67 m (8H, CH2CH2CH2CH2), 3.33 d.t (4H, NCH2, J = 5.5, JCH, NH = 6.4), 3.67 t (4H, OCH2, J = 5.5),
3.96 d.d (2H, cis-H, 2J = 2.0, Jcis = 6.7), 4.08 d.d (2H, trans-H, 2J = 2.0, Jtrans = 14.1),
3
3
3
3
6.43 d.d (2H, OCH, Jcis = 6.7, Jtrans = 14.1), 7.58 br.s (2H, NH)
2
0.93 t (6H, CH3), 1.63 m (4H, NCHCH2CH3), 3.72 3.98 m (6H, NCH, OCH2), 3.99 d.d (2H, cis-H, J = 1.9,
3Jcis = 6.6), 4.15 d.d (2H, trans-H, J = 1.9, Jtrans = 14.2), 6.44 d.d (2H, OCH, Jcis = 6.6, Jtrans = 14.2),
2
3
3
3
7.55 br.s (2H, NH)
2
3
2
IIIa
IIIb
3.65 3.80 m (8H, NCH2CH2O), 4.03 d.d (2H, cis-H, J = 2.2, Jcis = 6.8), 4.20 d.d (2H, trans-H, J = 2.2,
3Jtrans = 14.3), 6.46 d.d (2H, OCH, 3Jcis = 6.8, 3Jtrans = 14.3), 6.95 br.s (2H, NH), 7.49 m (4H, C6H4)
2
3
2.02 m (4H, 2CH2CH2CH2), 3.65 3.85 m (8H, NCH2, OCH2), 3.95 d.d (2H, cis-H, J = 2.0, Jcis = 6.7),
2
3
3
3
4.17 d.d (2H, trans-H, J = 2.0, Jtrans = 14.0), 6.39 d.d (2H, OCH, Jcis = 6.7, Jtrans = 14.0), 7.10 br.s
(2H, NH), 7.75 m (4H, C6H4)
2
3
IIIc
IIId
1.71 m (8H, CH2CH2CH22CH2), 3.55 3.80 m (8H, NCH2, OCH2), 3.96 d.d (2H, cis-H, J = 1.8, Jcis = 6.6),
3 3 3
4.14 d.d (2H, trans-H, J = 1.8, Jtrans = 13.8), 6.41 d.d (2H, OCH, Jcis = 6.6, Jtrans = 13.8), 7.04 br.s
(2H, NH), 7.76 m (4H, C6H4)
0.98 t (6H, CH3), 1.64 m (4H, CHCH2CH3), 3.77 4.05 m (8H, OCH2, NCH, cis-H), 4.19 d.d (2H, trans-H,
3
3
3
2J = 1.9, Jtrans = 14.1), 6.44 d.d (2H, OCH, Jcis = 6.7, Jtrans = 14.1), 7.06 br.s (2H, NH), 7.59 m (4H,
C6H4)
EXPERIMENTAL
REFERENCES
The IR spectra were recorded on a Specord 75IR
spectrometer from samples pelleted with KBr. The
1H NMR spectra were obtained on a Jeol FX 90Q
instrument (90 MHz) in CDCl3 at 27 C using HMDS
as internal reference. Commercial diethyl oxalate and
phthalimide were used. Vinyloxyalkylamines Ia Id
were prepared by vinylation of the corresponding
amino alcohols with acetylene, following a procedure
analogous to that reported in [7].
1. Kukharev, B.F., Stankevich, V.K., and Klimen-
ko, G.R., Usp. Khim., 1995, vol. 64, no. 6, p. 562.
2. Amosova, S.V., Antsiferova, L.I., Shaulina, L.P.,
Golentovskaya, N.P., Toryashinova, D.-S.D., and
Kustova, S.A., Zh. Prikl. Khim., 2001, vol. 74, no. 1,
p. 39.
3. Lavrov, V.I., Parshina, L.N., Nedolya, N.A., Pap-
sheva, N.P., Stankevich, V.K., and Kukharev, B.F.,
Zh. Org. Khim., 1990, vol. 26, no. 2, p. 259.
N,N -Bis(vinyloxyalkyl)oxamides IIa IId (typical
procedure). Vinyloxyalkylamine Ia Id, 0.2 mol,
was added with stirring to 0.1 mol of diethyl oxalate
at such a rate that the temperature did not exceed
30 C. After cooling to room temperature, the mixture
solidified and was recrystallized from ethanol.
4. Nedolya, N.A., Tolmachev, S.V., and Zinov’eva, V.P.,
Russ. J. Org. Chem., 2001, vol. 37, no. 8, p. 1074.
5. Nedolya, N.A., Gerasimova, V.V., and Trofi-
mov, B.A., Sulfur Lett., 1991, vol. 13, no. 5, p. 203;
Nedolya, N.A., Gerasimova, V.V., and Trofi-
mov, B.A., Zh. Org. Khim., 1992, vol. 28, no. 1, p. 8.
N,N -Bis(vinyloxyalkyl)phthalamides IIIa IIId
(typical procedure). A mixture of 0.01 mol of phthal-
imide, 0.025 mol of vinyloxyalkylamine Ia Id, and
40 ml of benzene was stirred at room temperature
until it became homogeneous ( 6 days). The solvent
was evaporated, and the precipitate was purified by
recrystallization from ethanol.
6. Tarasova, O.A., Trofimov, B.A., Al’pert, M.L.,
Ivanova, N.I., Amosova, S.V., and Voronkov, M.G.,
Zh. Org. Khim., 1981, vol. 17, no. 12, p. 2628;
Nedolya, N.A., Dymchenko, V.I., and Sinitsina, L.E.,
Zh. Org. Khim., 1994, vol. 30, no. 4, p. 503.
7. US Patent no. 2969395, 1961; Ref. Zh., Khim., 1962,
no. 8L 64.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 38 No. 10 2002