ACID-CATALYZED TRANSFORMATIONS OF N-[(VINYLOXY)ALKYL]-...
1037
(
3 ×15 mL), the extract was dried over potassium
100.62 MHz, respectively, using CDCl as solvent and
3
carbonate and evaporated, and the residue was dried
under reduced pressure.
reference (CHCl , δ 7.26 ppm; CDCl , δ 77.00 ppm).
3
3
C
The IR spectra were recorded on a Bruker Vertex-70
spectrometer from films or KBr disks. The elemental
analyses were obtained on a Flash EA 1112 analyzer.
N-[2-(Vinyloxy)ethyl]- and N-[3-(vinyloxy)propyl]-
2
,2′-[Ethane-1,1-diylbis(oxy)]diethanamine (5a).
–
1
Yield 2.13 g (72%) (69% [1]). IR spectrum, ν, cm :
3
1
1
5
373, 3295, 3196, 2987, 2926, 2867, 1597, 1466,
459, 1446, 1386, 1339, 1311, 1259, 1197, 1133, 1099,
036, 1014, 991, 936, 864, 812, 755, 661, 612, 542,
2
,2,2-trifluoroacetamides 1a and 1c were synthesized
as described in [14].
1
04, 471. H NMR spectrum, δ, ppm: 1.29–1.31 m
3
REFERENCES
(
7H, CH , NH ), 2.84 t (4H, CH N, J = 5.3 Hz), 3.40–
3
2
2
3
.45 m and 3.58–3.63 m (2H each, OCH ), 4.71 q (1H,
2
3
13
1. Frechet, J.M.J., Standley, S.M., Jain, R., and Lee, C.C.,
US Patent no. 8137700, 2012; Chem. Abstr., 2012,
vol. 156, no. 390999.
CH, J = 5.3 Hz). C NMR spectrum, δ , ppm: 19.70
C
(
CH ), 42.02 (CH N), 67.67 (OCH ), 100.08 (CH).
3 2 2
Found, %: C 48.38; H 10.94; N 18.73. C H N O .
6
16
2
2
2
3
4
. Hong, B.J., Chipre, A.J., and Nguyen, S.T., J. Am.
Chem. Soc., 2013, vol. 135, p. 17655.
. Shim, M.S. and Kwon, Y.J., Biomacromolecules, 2008,
vol. 9, p. 444.
. Paramonov, S.E., Bachelder, E.M., Beaudette, T.T.,
Standley, S.M., Lee, C.C., Dashe, J., and
Fréchet, J.M.J., Bioconjugate Chem., 2008, vol. 19,
p. 911.
Calculated, %: C 48.63; H 10.88; N 18.90.
,1′-[Ethane-1,1-diylbis(oxy)]bis(2-methylpro-
pan-2-amine) (5b). Yield 2.08 g (51%). IR spectrum,
1
–
1
ν, cm : 3356, 3280, 3072, 2967, 2927, 2872, 1668,
1
1
7
1
1
590, 1471, 1382, 1365, 1345, 1277, 1246, 1209,
189, 1151, 1136, 1101, 1051, 1003, 909, 885, 770,
1
25, 655, 623, 534, 452. H NMR spectrum, δ, ppm:
3
.01 s (12H, CH ), 1.22 d (3H, CHCH , J = 5.2 Hz),
5. Yu, Z.-Q., Yan, J.-J., You, Y.-Z., and Zhou, Q.-H., Int. J.
Nanomed., 2012, vol. 7, p. 5819.
6. Wang, Z.-K., Wang, L.-H., Sun, J.-T., Han, L.-F., and
3
3
.40 br.s (4H, NH ), 3.05 d and 3.27 d (2H each,
2
2
3
OCH , J = 8.8 Hz), 4.63 q (1H, CH, J = 5.2 Hz).
2
1
3
C NMR spectrum, δ , ppm: 19.39 (CHCH ), 27.27
Hong, Ch.-Y., Polymer Chem., 2013, vol. 4, p. 1694.
C
3
and 27.35 (CH ), 49.64 (C), 75.51 (OCH ), 100.40
7. Lim, H., Noh, J., Kim, Y., Kim, H., Kim, J., Khang, G.,
3
2
and Lee, D., Biomacromolecules, 2013, vol. 14, p. 240.
(
CH). Found, %: C 58.92; H 11.66; N 13.78.
C H N O . Calculated, %: C 58.79; H 11.84; N 13.71.
8. Qin, B., Li, X., and Liang, B., CN Patent
no. 103435504, 2013; Chem. Abstr., 2013, vol. 160,
no. 100988.
1
0
24
2
2
3
,3′-[Ethane-1,1-diylbis(oxy)]dipropan-1-amine
–
1
(
5c). Yield 2.25 g (64%). IR spectrum, ν, cm : 3348,
9
. Liang, B., Qin, B., Pastine, S., and Li, X., WO Patent
Appl. no. 2013007128; Chem. Abstr., 2013, vol. 158,
no. 159400.
3
1
1
4
294, 2983, 2929, 2872, 1665, 1656, 1650, 1644,
578, 1572, 1567, 1562, 1475, 1470, 1381, 1341,
307, 1131, 1100, 1076, 956, 887, 818, 763, 665, 534,
1
0. Tarasova, O.A., Trofimov, B.A., Al’pert, M.L., Ivano-
va, N.I., Amosova, S.A., and Voronkov, M.G., Zh. Org.
Khim., 1981, vol. 17, p. 2628.
1
21. H NMR spectrum, δ, ppm: 1.24–1.30 m (7H,
CH , NH ), 1.71 m (4H, CH CH N), 2.80 t (4H,
3
2
2
2
3
CH N, J = 6.7 Hz), 3.46–3.51 m and 3.62–3.68 m (2H
2
1
1. Shostakovsky, M.F. and Chekulaeva, I.A., Bull. Acad.
3
13
each, OCH ), 4.66 q (1H, CH, J = 5.3 Hz). C NMR
2
Sci. USSR, Div. Chem. Sci., 1955, vol. 4, p. 127.
2. Shostakovsky, M.F. and Chekulaeva, I.A., Bull. Acad.
Sci. USSR, Div. Chem. Sci., 1957, vol. 6, p. 79.
3. Kukharev, B.F., Stankevich, V.K., and Klimenko, G.R.,
Russ. Chem. Rev., 1995, vol. 64, p. 523.
14. Lobanova, N.A., Stankevich, V.K., and Kukharev, B.F.,
spectrum, δ , ppm: 19.75 (CH ), 33.68 (CH CH N),
C
3
2
2
1
1
3
9.51 (CH N), 63.39 (OCH ), 99.88 (CH). Found, %:
2 2
C 54.69; H 11.23; N 15.91. C H N O . Calculated, %:
8
20
2
2
C 54.51; H 11.44; N 15.89.
1
13
The H and C NMR spectra were measured on
a Bruker DPX-400 spectrometer at 400.13 and
Russ J. Org. Chem., 2012, vol. 48, p. 1289.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 7 2015