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J. Uenishi et al.
Paper
Synthesis
IR (CHCl3): 3238, 1653, 1618, 1506 cm–1
.
13C NMR (100 MHz, DMSO-d6): δ = 164.1, 152.9, 139.6, 137.4, 136.0,
134.9, 129.6, 129.0, 127.6, 122.0, 104.2, 60.0, 58.1, 56.1, 56.0.
MS (FAB): m/z = 473 [M + H]+.
HRMS-FAB: m/z [M + H]+ calcd for C28H29N2O5: 473.2076; found:
473.2072.
1H NMR (400 MHz, DMSO-d6): δ = 8.74 (d, J = 7.3 Hz, 2 H), 7.60–7.58
(m, 4 H), 7.49 (d, J = 15.5 Hz, 2 H), 7.49–7.39 (m, 6 H), 7.08 (d, J = 3.2
Hz, 1 H), 7.01 (d, J = 9.1 Hz, 1 H), 6.99 (t, J = 7.5 Hz, 1 H), 6.93 (dd, J =
9.1, 3.2 Hz, 1 H), 6.80 (d, J = 15.5 Hz, 2 H), 3.80 (s, 3 H), 3.75 (s, 3 H).
13C NMR (100 MHz, DMSO-d6): δ = 164.8, 154.0, 151.5, 140.2, 135.8,
130.5, 130.2, 129.9, 128.5, 122.9, 114.9, 113.8, 113.3, 57.1, 56.4, 54.5.
Anal. Calcd for C28H28N2O5: C, 71.17; H, 5.97; N, 5.93. Found: C, 71.47;
H, 5.97; N, 5.93.
MS (FAB): m/z = 443 [M + H]+.
HRMS-FAB: m/z [M + H]+ calcd for C27H27N2O4: 443.1971; found:
(2E,2′E)-N,N′-[(4-Cyanophenyl)methylene]bis(3-phenylacryl-
amide) (23)
443.1962.
White solid; yield: 554 mg (68%); mp 255–259 °C; Rf = 0.29 (50%
EtOAc–hexane).
Anal. Calcd for C27H26N2O4: C, 73.28; H, 5.92; N, 6.33. Found: C, 73.45;
H, 5.80; N, 6.57.
IR (CHCl3): 3215, 2231, 1669, 1624, 1558, 1520 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 9.09 (d, J = 7.7 Hz, 2 H), 7.93 (d, J =
8.2 Hz, 2 H), 7.65 (d, J = 8.2 Hz, 2 H), 7.62–7.61 (m, 4 H), 7.56 (d, J =
15.5 Hz, 2 H), 7.50–7.40 (m, 6 H), 6.86 (t, J = 7.7 Hz, 1 H), 6.83 (d, J =
15.5 Hz, 2 H).
(2E,2′E)-N,N′-[(3,4-Dimethoxyphenyl)methylene]bis(3-phenyl-
acrylamide) (20)
White solid; yield: 646 mg (73%); mp 255–258 °C; Rf = 0.20 (50%
EtOAc–hexane).
IR (CHCl3): 3274, 1657, 1628, 1559, 1519 cm–1
.
13C NMR (100 MHz, DMSO-d6): δ = 165.4, 146.4, 140.9, 135.6, 133.4,
130.7, 129.9, 128.6, 128.5, 122.3, 119.7, 111.5, 58.6.
MS (FAB): m/z = 408 [M + H]+.
HRMS-FAB: m/z [M + H]+ calcd for C26H22N3O2: 408.1712; found:
408.1716.
1H NMR (400 MHz, DMSO-d6): δ = 8.86 (d, J = 7.7 Hz, 2 H), 7.61–7.59
(m, 4 H), 7.52 (d, J = 16.0 Hz, 2 H), 7.48–7.39 (m, 6 H), 7.07 (s, 1 H),
7.00 (s, 2 H), 6.82 (d, J = 16.0 Hz, 2 H), 6.77 (t, J = 7.7 Hz, 1 H), 3.81 (s, 3
H), 3.78 (s, 3 H).
13C NMR (100 MHz, DMSO-d6): δ = 165.0, 149.6, 149.4, 140.4, 135.8,
133.5, 130.5, 129.9, 128.5, 122.8, 119.5, 112.5, 111.3, 58.6, 56.6, 56.5.
Anal. Calcd for C26H21N3O2: C, 76.64; H, 5.19; N, 10.31. Found: C,
76.44; H, 4.92; N, 10.12.
MS (FAB): m/z = 443 [M + H]+.
HRMS-FAB: m/z [M + H]+ calcd for C27H27N2O4: 443.1971; found:
(2E,2′E)-N,N′-[(4-Tolyl)methylene]bis(3-phenylacrylamide) (24)
443.1967.
White solid; yield: 705 mg (89%); mp 279–281 °C; Rf = 0.33 (40%
EtOAc–hexane).
IR (CHCl3): 3265, 1658, 1630, 1562, 1514 cm–1
Anal. Calcd for C27H26N2O4: C, 73.28; H, 5.92; N, 6.33. Found: C, 73.10;
H, 5.92; N, 6.36.
.
1H NMR (400 MHz, DMSO-d6): δ = 8.89 (d, J = 7.7 Hz, 2 H), 7.61–7.59
(m, 4 H), 7.53 (d, J = 16.0 Hz, 2 H), 7.48–7.39 (m, 6 H), 7.34 (d, J = 8.2
Hz, 2 H), 7.24 (d, J = 8.2 Hz, 2 H), 6.84 (d, J = 16.0 Hz, 2 H), 6.80 (t, J =
7.7 Hz, 1 H), 2.34 (s, 3 H).
(2E,2′E)-N,N′-[(3,5-Dimethoxyphenyl)methylene]bis(3-phenyl-
acrylamide) (21)
White solid; yield: 539 mg (61%); mp 261–263 °C; Rf = 0.46 (70%
EtOAc–hexane).
IR (CHCl3): 3253, 1653, 1620, 1523 cm–1
13C NMR (100 MHz, DMSO-d6): δ = 165.1, 140.4, 138.1, 137.9, 135.8,
130.5, 129.9, 129.8, 128.5, 127.3, 122.7, 58.5, 21.6.
.
1H NMR (400 MHz, DMSO-d6): δ = 8.89 (d, J = 7.7 Hz, 2 H), 7.61–7.59
(m, 4 H), 7.53 (d, J = 16.0 Hz, 2 H), 7.48–7.39 (m, 6 H), 6.82 (d, J = 16.0
Hz, 2 H), 6.75 (t, J = 7.7 Hz, 1 H), 6.63 (d, J = 1.8 Hz, 2 H), 6.52 (t, J = 1.8
Hz, 1 H), 3.79 (s, 6 H).
13C NMR (100 MHz, DMSO-d6): δ = 165.1, 161.5, 143.5, 140.5, 135.7,
130.5, 129.9, 128.5, 122.7, 105.7, 100.2, 58.7, 56.2.
MS (FAB): m/z = 397 [M + H]+.
HRMS-FAB: m/z [M + H]+ calcd for C26H25N2O2: 397.1916; found:
397.1920.
Anal. Calcd for C26H24N2O2: C, 78.76; H, 6.10; N, 7.07. Found: C, 78.58;
H, 6.19; N, 7.04.
MS (FAB): m/z = 443 [M + H]+.
HRMS-FAB: m/z [M + H]+ calcd for C27H27N2O4: 443.1971; found:
(2E,2′E)-N,N′-[(4-tert-Butylphenyl)methylene]bis(3-phenylacryl-
amide) (25)
443.1965.
White solid; yield: 728 mg (83%); mp 288–290 °C; Rf = 0.63 (50%
EtOAc–hexane).
IR (CHCl3): 3220, 1654, 1558, 1540, 1520, 1508 cm–1
Anal. Calcd for C27H26N2O4: C, 73.28; H, 5.92; N, 6.33. Found: C, 73.54;
H, 5.85; N, 6.39.
.
1H NMR (400 MHz, DMSO-d6): δ = 8.73 (d, J = 7.7 Hz, 2 H), 7.55 (d, J =
7.3 Hz, 4 H), 7.47 (d, J = 15.5 Hz, 2 H), 7.42–7.32 (m, 10 H), 6.77 (d, J =
15.5 Hz, 2 H), 6.74 (t, J = 7.7 Hz, 1 H), 1.27 (s, 9 H).
(2E,2′E)-N,N′-[(3,4,5-Trimethoxyphenyl)methylene]bis(3-phenyl-
acrylamide) (22)
White solid; yield: 491 mg (52%); mp 253–256 °C; Rf = 0.64 (EtOAc).
13C NMR (100 MHz, DMSO-d6): δ = 164.9, 151.0, 140.2, 138.1, 135.7,
130.3, 129.7, 128.3, 126.9, 125.9, 122.7, 58.5, 35.0, 31.9.
IR (CHCl3): 3213, 1655, 1621, 1558, 1496 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 9.18 (d, J = 7.7 Hz, 2 H), 7.98 (d, J =
6.8 Hz, 4 H), 7.90 (d, J = 16.0 Hz, 2 H), 7.85–7.79 (m, 6 H), 7.21–7.15
(m, 5 H), 4.21 (s, 6 H), 4.08 (s, 3 H).
MS (FAB): m/z = 439 [M + H]+.
HRMS-FAB: m/z [M + H]+ calcd for C29H31N2O2: 439.2385; found:
439.2393.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 2976–2984