16 Liu et al.
(NH, s), 8.769 (NH, s), 8.257 (1H, s), 7.859 (2H, d,
J = 7.6 Hz), 7.532 (1H, t, J = 7.6 Hz), 7.303 (4H,
d, J = 8.4 Hz) 7.266 (4H, m), 7.649 (4H, d, J = 8.4
Hz), 3.954 (4H, m); 13C NMR (75 MHz, DMSO-d6)
δ: 167.30 (2C), 166.62 (2C), 153.73 (2C), 147.36 (2C),
134.58 (2C), 133.36 (2C), 129.80 (2C), 128.54 (1C),
126.76 (1C), 125.72 (2C), 123.90 (4C), 120.61 (4C),
116.19 (2C), 45.53 (2C); MS (ESI) m/z: 537.0 [M +
H]+; Anal. Calcd. for C30H24N4O6: C, 67.16; H, 4.51;
N, 10.44. Found: C, 67.13; H, 4.46; N, 10.40.
1,3-Bis(4-(aminoacetamido)phenoxy)benzene
Hydrochloride 5d
Compound 5d was prepared from 4d following the
general procedure described above for 5a and ob-
tained in 36.6% yield as a white solid: mp 258.9–
1
261.4◦C; H NMR (300 MHz, D2O) δ: 7.253 (4H, d,
J = 8.4 Hz), 7.149 (1H, t, J = 8.0 Hz), 6.822 (4H, d,
J = 8.4 Hz), 6.583 (2H, d, J = 8.0 Hz), 6.426 (1H,
s), 3.830 (4H, s); 13C NMR(75 MHz, D2O) δ:164.04
(2C), 156.85 (2C), 152.24 (2C), 130.85 (2C), 129.68
(1C), 121.87 (4C), 118.37 (4C), 112.21 (2C), 107.51
(1C), 39.56 (2C); MS (ESI) m/z: 407.2 [M – 2Cl – H]+;
Anal. Calcd. for C22H24Cl2N4O4: C, 55.12; H, 5.05; N,
11.69. Found: C, 55.09; H, 5.02; N, 11.65.
10,30-Dichloro-2,8-dioxa-14,17,23,26-tetraoxo-
13,16,24,27-tetraazapentacyclo[26.2.2.29,12.13, 7
.118,22] pentatriacont -3,5,7,9,11,18,20,22,
28,30,31,33-dodecaene 6c
11,31-Dichloro-2,9-dioxa-15,18,24,27-tetraoxo-
14,17,25,28-tetraazapentacyclo
Compound 6c was prepared form 5c following the
general procedure described above for 6a and ob-
tained in 51.6% yield as a white solid: mp 312.3–
314.5◦C; 1H NMR (300 MHz, DMSO-d6) δ: 10.167
(NH, s), 8.824 (NH, s), 8.292 (1H, s), 7.929 (2H, d, J
= 6.6 Hz),7.863 (2H, d, J = 2.3 Hz), 7.566 (1H, t, J =
7.5 Hz), 7.459 (1H, d, J = 8.3 Hz),7.403 (2H, d, J = 9.0
Hz), 7.084 (2H, d, J = 9.0 Hz), 6.972 (2H, d, J = 2.3
Hz),5.785 (1H, s), 3.989–3.974 (4H, m); 13C NMR (75
MHz, DMSO-d6) δ: 168.10 (2C), 166.49 (2C), 157.66
(2C), 145.56 (2C), 136.28 (2C), 134.34 (2C), 131.45
(2C), 129.86 (1C), 128.50 (1C), 126.78 (2C), 124.47
(1C), 121.48 (2C), 120.98 (2C), 119.52 (2C), 112.85
(2C), 101.50 (1C), 44.71 (2C); MS (ESI) m/z: 603.2
[M – H]−; Anal. Calcd. for C30H22Cl2N4O6: C, 59.52;
H, 3.66; N, 9.25. Found: C, 59.49; H, 3.64; N, 9.21.
[27.2.2.210,13.119,23.03,8] pentatriacont-
3,5,7,10,12,19,21,23,29,31,33,34-dodecaene 6a
The cyclization was carried out under high dilution
condition. A suspension of compound 5a (24.3 mg,
0.05 mmol) and Et3N (1.0 mL) in dry CH2Cl2 (30 mL)
was added dropwise over 30 min at 0◦C to a solution
of iso-phthaloyl dichloride (12 mg, 0.06 mmol) in dry
CH2Cl2 (50 mL). The mixture was stirred for 12 h at
30◦C. After filtration, the mixture was concentrated
in vacuo to give the residue that was dissolved in
dry CH2Cl2, then washed with water, dried in vacuo
over anhydrous Na2SO4, and evaporated. The crude
product was purified by column chromatography
(methanol: EtOAc = 1:10) to give 6a (0.012 g, 40%)
as a yellow powder: mp 323.8–326.1◦C; 1H NMR (300
MHz, DMSO-d6) δ: 9.897 (NH, s), 8.674 (NH, s), 8.201
(1H, s), 7.875(2H, d, J = 7.6 Hz), 7.685 (2H, s), 7.543
(1H, t, J = 7.6 Hz), 7.317 (4H, s), 7.091 (2H, d, J =
9.0 Hz), 6.570 (2H, d, J = 9.0 Hz), 3.960 (4H, m);
13C NMR (75 MHz DMSO-d6) δ: 167.77 (2C), 166.56
(2C), 148.90 (2C), 146.62 (2C), 134.51 (2C), 134.28
(2C), 130.01 (2C), 128.72 (1C), 126.93 (2C), 126.34
(1C), 123.84 (2C), 121.64 (2C), 120.84 (2C), 119.18
(2C), 116.76 (2C), 45.66 (2C); MS (ESI) m/z: 604.9
[M + H]+; Anal. Calcd. for C30H22Cl2N4O6: C, 59.52;
H, 3.66; N, 9.25. Found: C, 59.50; H, 3.60; N, 9.22.
2,8-Dioxa-14,17,23,26-tetraoxo-13,16,24,27-
tetraazapentacyclo[26.2.2.29,12.13,7.118,22
]
pentatriacont -3,5,7,9,11,18,20,22,28,30,31,33-
dodecaene 6d
Compound 6c was prepared from 5c following the
general procedure described above for 6a and ob-
tained in 48.6% yield as a yellow solid: mp 310.2–
312.5◦C; 1H NMR (300 MHz, DMSO-d6) δ: 9.991
(NH, s), 8.822 (NH, s), 8.334 (1H, s), 7.915 (2H, d,
J = 7.6 Hz), 7.582 (1H, d, J = 7.6 Hz), 7.531 (4H, d,
J = 8.7 Hz), 7.388 (1H, t, J = 8.1 Hz), 6.961 (4H,
d, J = 8.5 Hz), 6.883 (2H, d, J = 8.1 Hz), 6.050
(1H, s), 3.977 (4H, s); 13C NMR(75 MHz, DMSO-
d6) δ: 167.70 (2C), 166.63 (2C), 158.21 (2C), 150.89
(2C), 134.97 (2C), 134.54 (2C), 131.38 (2C), 129.98
(1C), 128.58 (1C), 126.72 (1C), 121.21 (4C), 119.31
(4C), 113.21 (2C), 103.80 (1C), 44.68 (2C); MS (ESI)
m/z: 535.5 [M – 1]−; Anal. Calcd. for C30H24N4O6: C,
67.16; H, 4.51; N, 10.44. Found: C, 67.11; H, 4.44; N,
10.41.
2,9-Dioxa-15,18,24,27-tetraoxo-14,17,25,28-
tetraazapentacyclo[27.2.210,13.119,23.03,8
]
pentatriacont-3,5,7,10,12,19,21,23,29,31,33,34-
dodecaene 6b
Compound 6b was prepared from 5b following the
general procedure described above for 6a and ob-
tained in 36.6% yield as a white powder: mp 308.4–
310.8◦C; 1H NMR (300 MHz, DMSO-d6) δ: 9.783
Heteroatom Chemistry DOI 10.1002/hc