C.-C. Liao et al. / Tetrahedron 64 (2008) 7977–7985
7983
(t, 4H, –OCOCH2, J¼7.25 Hz), 3.93 (t, 4H, –OCH2, J¼6.52 Hz), 6.43 (d,
4.14. Bis(4-(6-(decyloxy)benzo[d]oxazol-2-yl)phenyl)glutarate
1a (m[3, n[10)
2H, Ar–H, J¼11.41 Hz), 6.55 (s, 2H, Ar–H), 7.17 (d, 4H, Ar–H,
J¼8.53 Hz), 7.25 (d, 2H, Ar–H, J¼8.75 Hz), 7.49 (s, 2H, –OH), 7.88 (d,
4H, Ar–H, J¼8.57 Hz), 8.58 (s, 2H, –NCH). 13C NMR (CDCl3):
d
14.12,
White solid, yield 69%. 1H NMR (CDCl3):
d
0.86 (t, 6H, –CH3,
22.68, 24.42, 26.00, 28.40, 28.51, 29.02, 29.17, 29.34, 29.58, 29.63,
29.67, 31.90, 34.09, 68.25, 100.54, 107.17, 116.37, 122.06, 128.40,
129.58, 133.67, 152.42, 152.84, 153.72, 160.38, 171.63.
J¼6.76 Hz),1.26–1.47 (m, 28H, –CH2),1.79–1.83 (m, 4H, –CH2), 2.20–
2.25 (m, 2H, –CH2), 2.77 (t, 4H, –OCOCH2, J¼7.17 Hz), 3.99 (t, 4H,
–OCH2, J¼6.49 Hz), 6.93 (d, 2H, Ar–H, J¼10.76 Hz), 7.07 (s, 2H, Ar–H),
7.24 (d, 4H, Ar–H, J¼8.06 Hz), 7.59 (d, 2H, Ar–H, J¼8.66 Hz), 8.20 (d,
4.10. Bis(4-((E)-(4-(dodecyloxy)-2-hydroxyphenylimino)-
methyl)phenyl)tridecanedioate 2 (m[11, n[12)
4H, Ar–H, J¼8.54 Hz). 13C NMR (CDCl3):
d 14.11, 19.90, 22.69, 26.06,
29.24, 29.33, 29.40, 29.57, 29.58, 31.90, 33.24, 68.91, 96.09, 113.50,
119.95, 122.13, 125.18, 128.52, 135.68, 151.72, 152.69, 157.93, 161.38,
170.94. MS (FAB): calcd for MHþ C51H62N2O8: 831.1, found: 831.0.
Yellow solid, yield 70%. 1H NMR (CDCl3):
d 0.86 (t, 6H, –CH3,
J¼6.39 Hz), 1.25–1.59 (m, 50H, –CH2), 1.73–1.91 (m, 8H, –CH2), 2.57
(t, 4H, –OCOCH2, J¼7.05 Hz), 3.92 (t, 4H, –OCH2, J¼6.34 Hz), 6.44 (d,
2H, Ar–H, J¼8.80 Hz), 6.55 (s, 2H, Ar–H), 7.16 (d, 4H, Ar–H,
J¼8.25 Hz), 7.25 (d, 2H, Ar–H, J¼8.80 Hz), 7.47 (s, 2H, –OH), 7.86 (d,
4.15. Bis(4-(6-(tetradecyloxy)benzo[d]oxazol-2-yl)phenyl)-
glutarate 1a (m[3, n[14)
4H, Ar–H, J¼8.23 Hz), 8.57 (s, 2H, –NCH). 13C NMR (CDCl3):
d
14.11,
White solid, yield 66%. 1H NMR (CDCl3):
d 0.87 (t, 6H, –CH3,
22.67, 24.83, 26.20, 28.59, 28.73, 28.92, 29.05, 29.19, 29.36, 29.41,
29.58, 29.64, 31.90, 34.63, 68.22, 100.45, 107.09, 116.20, 122.04,
128.13, 129.45, 133.72, 152.30, 152.82, 153.74, 160.30, 171.95.
J¼6.85 Hz), 1.26–1.50 (m, 44H, –CH2), 1.79–1.82 (m, 4H, –OCH2CH2),
2.21–2.24 (m, 2H, –CH2), 2.76 (t, 4H, –OCOCH2, J¼7.18 Hz), 4.00 (t,
4H, –OCH2, J¼6.52 Hz), 6.93 (d, 2H, Ar–H, J¼8.71 Hz), 7.07 (s, 2H,
Ar–H), 7.25 (d, 4H, Ar–H, J¼8.78 Hz), 7.59 (d, 2H, Ar–H, J¼8.72 Hz),
4.11. Bis(4-(6-(dodecyloxy)benzo[d]oxazol-2-yl)phenyl)-
glutarate 1a (m[3, n[12)
8.20 (d, 4H, Ar–H, J¼8.68 Hz). 13C NMR (CDCl3):
d 13.95, 19.98,
22.59, 26.02, 29.24, 29.26, 29.33, 29.51, 29.53, 29.58, 29.60, 29.62,
31.86, 33.30, 69.05, 96.28, 113.51, 119.95, 122.00, 125.26, 128.50,
135.89, 151.77, 152.79, 158.00, 161.39, 170.72. MS (FAB): calcd for
MHþ C59H78N2O8: 943.3, found: 943.0.
The
mixture
of
bis(4-((E)-(4-(dodecyloxy)-2-hydroxy-
phenylimino)methyl)phenyl)glutarate (0.20 g, 0.22 mmol) and
lead acetate Pb(OAc)4 (0.12 g, 0.26 mmol) dissolved in 20 ml of
CHCl3 was refluxed for 2 h. The solution was filtered and the filtrate
was extracted with CH2Cl2/H2O. The organic layers were collected
and dried (MgSO4). The product isolated as white solids were
obtained after recrystallization from CH2Cl2/MeOH. Yield 70%. 1H
4.16. Bis(4-(6-(hexadecyloxy)benzo[d]oxazol-2-yl)phenyl)-
glutarate 1a (m[3, n[16)
White solid, yield 77%. 1H NMR (CDCl3):
d 0.87 (t, 6H, –CH3,
NMR (CDCl3):
d
0.85 (t, 6H, –CH3, J¼7.09 Hz), 1.26–1.50 (m, 36H,
J¼6.88 Hz), 1.26–1.49 (m, 52H, –CH2), 1.80–1.82 (m, 4H, –OCH2CH2),
2.22–2.24 (m, 2H, –CH2), 2.77 (t, 4H, –OCOCH2, J¼7.21 Hz), 4.01 (t,
4H, –OCH2, J¼6.55 Hz), 6.93 (d, 2H, Ar–H, J¼8.74 Hz), 7.07 (s, 2H,
Ar–H), 7.25 (d, 4H, Ar–H, J¼8.78 Hz), 7.59 (d, 2H, Ar–H, J¼8.72 Hz),
–CH2), 1.78–1.84 (m, 4H, –CH2), 2.21–2.24 (m, 2H, –CH2), 2.77 (t, 4H,
–OCOCH2, J¼7.20 Hz), 4.00 (t, 4H, –OCH2, J¼6.55 Hz), 6.94 (d, 2H,
Ar–H, J¼8.71 Hz), 7.07 (s, 2H, Ar–H), 7.26 (d, 4H, Ar–H, J¼7.31 Hz),
7.60 (d, 2H, Ar–H, J¼8.73 Hz), 8.21 (d, 4H, Ar–H, J¼8.67 Hz). 13C
8.20 (d, 4H, Ar–H, J¼8.68 Hz). 13C NMR (CDCl3):
d 13.94, 19.98,
NMR (CDCl3):
d
14.12, 19.88, 22.70, 26.06, 29.23, 29.36, 29.40, 29.58,
22.59, 26.02, 29.24, 29.27, 29.33, 29.51, 29.53, 29.58, 29.62, 31.86,
33.30, 69.05, 96.28, 113.51, 119.95, 122.00, 125.26, 128.50, 135.89,
151.77, 152.79, 158.00, 161.39, 170.72. MS (FAB): calcd for MHþ
C63H86N2O8: 999.4, found: 999.1.
29.61, 29.65, 29.67, 31.93, 33.24, 68.91, 96.09, 113.56, 119.91, 122.15,
125.06, 128.57, 135.49, 151.68, 152.73, 157.96, 161.37, 170.95. MS
(FAB): calcd for MHþ C55H70N2O8: 887.2, found: 887.0.
4.12. Bis(4-(6-(hexyloxy)benzo[d]oxazol-2-yl)phenyl)-
glutarate 1a (m[3, n[6)
4.17. Bis(4-(6-(octyloxy)benzo[d]oxazol-2-yl)phenyl)-
heptanedioate 1c (m[5, n[8)
White solid, yield 65%. 1H NMR (CDCl3):
d
0.89 (t, 6H, –CH3,
White solid, yield 64%. 1H NMR (CDCl3):
d 0.87 (t, 6H, –CH3,
J¼7.14 Hz), 1.33–1.49 (m, 12H, –CH2), 1.78–1.83 (m, 4H, –CH2), 2.20–
2.23 (m, 2H, –CH2), 2.77 (t, 4H, –OCOCH2, J¼7.21 Hz), 4.00 (t, 4H,
–OCH2, J¼6.54 Hz), 6.93 (d, 2H, Ar–H, J¼8.72 Hz), 7.07 (s, 2H, Ar–H),
7.25 (d, 4H, Ar–H, J¼7.56 Hz), 7.59 (d, 2H, Ar–H, J¼8.72 Hz), 8.20 (d,
J¼6.51 Hz), 1.28–1.57 (m, 22H, –CH2), 1.79–1.85 (m, 8H, –CH2), 2.63
(t, 4H, –OCOCH2, J¼7.32 Hz), 3.98 (t, 4H, –OCH2, J¼6.51 Hz), 6.92 (d,
2H, Ar–H, J¼8.68 Hz), 7.05 (s, 2H, Ar–H), 7.22 (d, 4H, Ar–H,
J¼8.51 Hz), 7.58 (d, 2H, Ar–H, J¼8.71 Hz), 8.18 (d, 4H, Ar–H,
4H, Ar–H, J¼8.66 Hz). 13C NMR (CDCl3):
d
14.05, 19.89, 22.62, 25.74,
J¼8.50 Hz). 13C NMR (CDCl3):
d 14.11, 22.67, 24.47, 26.07, 28.45,
29.20, 31.60, 33.24, 68.89, 96.07, 113.49, 119.96, 122.13, 125.18,
128.52, 135.69, 151.70, 152.67, 157.91, 161.37, 170.97. MS (FAB): calcd
for MHþ C43H46N2O8: 718.8, found: 719.0.
29.25, 29.38, 31.83, 34.12, 68.88, 96.05, 113.46, 119.93, 122.15,
125.04, 128.49, 135.68, 151.68, 152.81, 157.89, 161.41, 171.58. MS
(FAB): calcd for MHþ C49H58N2O8: 803.0, found: 803.0.
4.13. Bis(4-(6-(octyloxy)benzo[d]oxazol-2-yl)phenyl)glutarate
1a (m[3, n[8)
4.18. Bis(4-(6-(dodecyloxy)benzo[d]oxazol-2-yl)phenyl)-
heptanedioate 1c (m[5, n[12)
White solid, yield 65%. 1H NMR (CDCl3):
d
0.87 (t, 6H, –CH3,
White solid, yield 64%. 1H NMR (CDCl3):
d 0.86 (t, 6H, –CH3,
J¼6.87 Hz), 1.28–1.47 (m, 20H, –CH2), 1.79–1.82 (m, 4H, –CH2),
2.22–2.23 (m, 2H, –CH2), 2.77 (t, 4H, –OCOCH2, J¼7.20 Hz), 3.99 (t,
4H, –OCH2, J¼6.57 Hz), 6.93 (d, 2H, Ar–H, J¼8.73 Hz), 7.07 (s, 2H,
Ar–H), 7.25 (d, 4H, Ar–H, J¼8.70 Hz), 7.59 (d, 2H, Ar–H, J¼8.74 Hz),
J¼6.90 Hz),1.25–1.48 (m, 38H, –CH2),1.79–1.86(m, 8H, –CH2), 2.63 (t,
4H, –OCOCH2, J¼7.38 Hz), 3.98 (t, 4H, –OCH2, J¼6.57 Hz), 6.92 (d, 2H,
Ar–H, J¼8.72 Hz), 7.05 (s, 2H, Ar–H), 7.22 (d, 4H, Ar–H, J¼8.70 Hz),
7.58 (d, 2H, Ar–H, J¼8.72 Hz), 8.19 (d, 4H, Ar–H, J¼8.70 Hz). 13C NMR
8.20 (d, 4H, Ar–H, J¼8.72 Hz). 13C NMR (CDCl3):
d
14.12, 19.89, 22.67,
(CDCl3): d 14.13, 22.70, 24.47, 26.07, 28.45, 29.24, 29.36, 29.41, 29.59,
26.07, 29.24, 29.25, 29.37, 31.83, 33.23, 68.90, 96.06, 113.49, 119.95,
122.13, 125.18, 128.52, 135.68, 151.70, 152.67, 157.91, 161.37, 170.97.
MS (FAB): calcd for MHþ C47H54N2O8: 774.9, found: 775.0.
29.62, 29.65, 29.67, 31.93, 34.13, 68.88, 96.05, 113.47, 119.93, 122.16,
125.04,128.50,135.67,151.68,152.81,157.89,161.41,171.59. MS (FAB):
calcd for MHþ C57H74N2O8: 915.2, found: 915.1.