Tripod-like compounds: Syntheses of tris(p- or o-amino phenoxymethyl)-propane, tris(p- or o-amino phenoxyethyl)amine, and their schiff base or salicyl derivatives

Article abstract of DOI:10.1081/SCC-100104066

Tris(nitrophenoxymethyl)propane and tris(nitrophenoxyethyl)amine, prepared by the reaction of trimethylol propane or triethanol amine with p- or o-chloronitrobenzene, were reduced to give the corresponding amines. The amines condensed with 2-pyridinecarboxaldehyde, 2-quinoline-carboxaldehyde, or salicylaldehyde to give the tripod Schiff bases. The tripodal salicylamides were obtained by condensation of salicylic acid with the amines in the presence of phosphorus trichloride.

Full text of DOI:10.1081/SCC-100104066

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TRIPOD-LIKE COMPOUNDS:
SYNTHESES OF TRIS(p- OR o-
AMINO PHENOXYMETHYL)-
PROPANE, TRIS(p- OR o-AMINO
PHENOXYETHYL)AMINE,
AND THEIR SCHIFF BASE OR
SALICYL DERIVATIVES
Huijie Lu a , Yaoting Fan a , Qinghuan Zhao a &
Yangjie Wu b
a Department of Chemistry , Zhengzhou
University , Zhengzhou, Henan, 450052, P.R. China
b Department of Chemistry , Zhengzhou
University , Zhengzhou, Henan, 450052, P.R. China
Published online: 02 Aug 2010.
To cite this article: Huijie Lu , Yaoting Fan , Qinghuan Zhao & Yangjie Wu (2001)
TRIPOD-LIKE COMPOUNDS: SYNTHESES OF TRIS(p- OR o-AMINO PHENOXYMETHYL)-
PROPANE, TRIS(p- OR o-AMINO PHENOXYETHYL)AMINE, AND THEIR SCHIFF BASE OR
SALICYL DERIVATIVES, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 31:10, 1531-1540, DOI: 10.1081/
SCC-100104066
To link to this article: http://dx.doi.org/10.1081/SCC-100104066

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SYNTHETIC COMMUNICATIONS, 31(10), 1531–1540 (2001)
TRIPOD-LIKE COMPOUNDS:
SYNTHESES OF TRIS(p- OR
o-AMINO PHENOXYMETHYL)-
PROPANE, TRIS(p- OR o-AMINO
PHENOXYETHYL)AMINE, AND
THEIR SCHIFF BASE OR
SALICYL DERIVATIVES
HuijieLu, Yaoting Fan, Qinghuan Zhao,
and YangjieWu *
Department of Chemistry, Zhengzhou University,
Zhengzhou, Henan, 450052, P.R. China
ABSTRACT
Tris(nitrophenoxymethyl)propane and tris(nitrophenoxy
ethyl)amine, prepared by the reaction of trimethylol
propane or triethanol amine with p- or o-chloronitrobenzene,
were reduced to give the corresponding amines. The amines
condensed with 2-pyridinecarboxaldehyde, 2-quinoline-
carboxaldehyde, or salicylaldehyde to give the tripod Schiff
bases. The tripodal salicylamides were obtained by condensa-
tion of salicylic acid with the amines in the presence of
phosphorus trichloride.
*Corresponding author.
1531
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

1532
LU ET AL.
Tripodal ionophores are attracting considerable attention in the
area of coordination chemistry.1–4 The attachment of three flexible,
donor-atom-containing chains to a framework leads to tripodal ligands,
which can form complexes with many cations, such as alkali metal, alkaline
earth metal, and transition metal cations. The ligands can be used for the
analysis and separation of metal ions,5–7 as well as for many catalytical or
biological applications.8–14 Our interest in the effective coordination
between transition metal ions and organic ligands, and in understanding
the mechanism of molecular transportation in organisms, prompted us to
design and synthesize a series of new tripod-like compounds containing
phenyl, pyridyl, salicyl, or quinolyl groups, which are usually biologically
active. The preliminary experiments indicated that these tripod-like
Scheme 1.

TRIPOD-LIKE COMPOUNDS
1533
compounds had excellent coordination ability with alkali metal, alkaline
earth metal, and transition metal. In this paper, we report the syntheses
of these new tripod-like compounds. The basic tripodal structure was con-
structed from trimethylol propane and triethanol amine. The synthetic
routes are shown in Scheme 1.
The reaction of trimethylol propane 1 with o- or p-chloronitrobenzene
in the presence of sodium hydride gave the corresponding nitro compounds
2 or 6. This nucleophilic substitution reaction took place easily and occurred
with an exotherm in a suitable solvent such as DMSO, DMF, or THF.
However, when the procedure was applied to triethanol amine 10 and
p-chloronitrobenzene, a side reaction occurred, and 4,40-dinitrophenyl
ether was isolated. This might result from the reaction of p-chloronitroben-
zene with p-nitrophenolate, which was possibly generated from the decom-
position of the desired product 11 (see Scheme 2). To prevent this side
reaction, the reaction of riethanol amine 10 with p-chloronitrobenzene
had to be carried out under mild conditions, and only DMSO could be
used as solvent. The reaction of triethanol amine 10 with o-chloronitroben-
zene was carried out analogous to the reaction with p-chloronitrobenzene.
All the nitro compounds were readily reduced by zinc powder or iron
powder in acid, giving the corresponding triamines 3, 7, 12, and 16. The
triamines reacted with salicylaldehyde, 2-pyridinecarboxaldehyde, or
2-quinolinecarboxaldehyde to give the corresponding Schiff bases 4, 8, 13,
and 17. Also, when the triamines were treated with salicylic acid in the
presence of phosphorus trichloride, the corresponding salicylamides 5, 9,
14, and 18 were isolated.
Scheme 2.
EXPERIMENTAL
IR spectra were recorded on
a
Perkin-Elmer FTIR1750
spectrophotometer.1H NMR spectra were recorded on a Bruke-DPX400
spectrometer, using CDCl3 as the solvent and tetramethylsilane as an inter-
nal standard. Elemental analyses were determined with a Carlo Erba 1106
elemental analyzer. DMSO was dried (CaH2) and distilled at reduced
pressure. All other reagents were used as commercial grade.

1534
LU ET AL.
Preparation of the Nitro Compounds: General Procedure
A mixture of 0.1 mol (13.4 g) of trimethylol propane 1 (or triethanol
amine 10) and 0.3 mol (11.5 g) of sodium hydride (60% suspension in
paraffin oil) in 30 mL of petroleum ether was stirred and refluxed for
about 20 m. The mixture was cooled and petroleum ether was decanted.
Dry DMSO (50 mL) was added to the residue solid. The suspension was
stirred for another 10 m. A solution of 0.4 mol (63 g) of p-chloronitro-
benzene (or o-chloronitrobenzene) in 40 mL of dry DMSO was added drop-
wise to the suspension with stirring and cooling. The temperature was kept
below 30ꢀC throughout the addition process. The resulting dark-brown
solution was stirred at 30ꢀC for about 20 h, and poured into 2 L of cold
water. The oil separated was treated with steam distillation to separate the
excess chloronitrobenzene. The residues were purified by recrystallization
(for a solid) or by chromatography (for an oil).
CH3CH2C[CH2O-(C6H4-p)-NO2]3 (2)
Yield 85%. Yellow solid, m.p. 177ꢀ–179ꢀC (acetone). Anal. found
(%): C, 58.18; H, 4.73; N, 8.35. Calc. for C24H23N3O9: C, 57.95; H, 4.63;
N, 8.45. IR (cmÀ1), 1595, 1508, 1337, 1300, 1253, 1110, 1032, 850. 1H NMR:
d (ppm)1.07(t, 3H, CH3), 1.92 (q, 2H, CH2C), 4.44 (s, 6H, 3CH2O),
7.22 ꢁ 8.19 (d, 12H, Ar-H).
CH3CH2[CH2O-(C6H4-o)-NO2]3 (6)
Yield 78%. Yellow solid, m.p. 97ꢀC (ethanol) Anal. found (%):
C, 57.99; H, 4.68; N, 8.33. Calc. for C24H23N3O9: C, 57.95; H, 4.63;
N, 8.45. IR (cmÀ1): 1608, 1523, 1352, 1283, 1160, 1012, 857, 741. 1H
NMR: d (ppm) 0.97 (t, 3H, CH3), 1.91 (q, 2H, CH2C), 4.34(s, 6H,
3CH2O), 7.07 ꢁ 7.88 (m, 12H, Ar-H).
N[CH2CH2O-(C6H4-p)-NO2]3 (11)
Yield 73%. Yellow Solid, m.p. 96ꢀC (acetone). Anal. found (%):
C, 56.34; H, 4.69; N, 10.81. Calc. for C24H24N4O9: C, 56.25; H, 4.69; N,
10.94. IR(cmÀ1, KBr pellet): 3120, 1510, 1340, 1260, 1020, 1170, 840.
1H NMR: d (ppm) 3.24 (t, 6H, 3NCH2), 4.20 (t, 6H, 3CH2O), 6.94(d, 6H,
Ar-H), 8.19 (d, 6H, Ar-H).

TRIPOD-LIKE COMPOUNDS
1535
N[CH2CH2O-(C6H4-o)-NO2]3 (15)
Yield 69%. Brown oil (chloroform as eluent). Anal. found (%):
C, 56.39; H, 4.73; N, 10.88. Calc. for C24H24N4O9: C, 56.25; H, 4.69;
N, 10.94. IR (cmÀ1): 1607, 1583, 1521, 1354, 1275, 1160, 1037, 851, 744.
1H NMR: d (ppm) 3.29 (t, 6H, 3 NCH2), 4.24 (t, 6H, 3CH2O), 6.97 ꢁ 7.82
(m, 12H, Ar-H).
Preparation of the Amines: General Procedure
To the mixture of 0.02 mol of the above prepared nitro compounds
and 0.1 mol of zinc powder in 50 mL of ethanol was added 50 mL of 15%
hydrochloric acid in 1 h at about 80ꢀC with stirring. After this addition, the
mixture was stirred for another hour at about 80ꢀC. Ethanol was distilled
off, and the mixture was cooled. A solution of 20% of sodium hydroxide
was added to neutralize the system. The system was extracted with methy-
lene chloride. The organic mixture was washed with an equal volume of
dilute hydrochloric acid. The water layer was basified with dilute sodium
hydroxide to separate the product. The crude product was further purified
by recrystallization or by chromatography.
CH3CH2C[CH2O-(C6H4-p)-NH2]3 (3)
Yield, 60%. gray solid, m.p. 87ꢀC (methanol). Anal. found (%): C,
70.97; H, 7.16; N, 9.98. Calc. for C24H29N3O3: C, 70.76; H, 7.13; N, 10.32.
IR (cmÀ1): 3411, 3397, 1620, 1512, 1230, 825. 1H NMR: d (ppm) 0.92 (t, 3H,
CH3), 1.66 (q, 2H, CH2C), 3.86 (s, 6H, 3CH2O), 4.80 (s, b, 6H, 3NH2),
6.51 ꢁ 6.67(m, 12H, Ar-H).
CH3CH2C[CH2O-(C6H4-o)-NH2]3 (7)
Yield, 57%. Dark-brown solid, m.p. 75ꢀC (methanol). Anal. found
(%): C, 70.81; H, 7.13; N, 10.21. Calc. for C24H29N3O3: C, 70.76; H,
7.13; N, 10.32. IR (cmÀ1): 3402, 3379, 3020, 1609, 1501, 1451, 1269, 1204,
1
849, 730. H NMR: d (ppm) 1.06 (t, 3H, CH3), 1.90 (q, 2H, CH2C), 3.58
(s, b, 6H, 3NH2), 4.20 (s, 6H, 3CH2O), 6.64–6.87 (m, 12H, Ar-H).
N[CH2CH2O-(C6H4-p)-NH2]3 (12)
Yield, 55%. Dark-brown solid, m.p. 68ꢀC (ethanol). Anal. found (%):
C, 68.33; H, 7.38; N, 13.19. Calc. for C24H30N4O3: C, 68.25; H, 7.11; N,

1536
LU ET AL.
13.27. IR (cmÀ1): 3399, 3289, 1610, 1508, 1233, 827. 1H NMR: d (ppm) 3.13
(t, 6H, 3NCH2), 4.03 (t, 6H, 3CH2O), 3.40 (b, overlap with 3NH2, 6H,
3NH2), 6.65–6.74 (m, 12H, Ar-H).
N[CH2CH2O-(C6H4-o)-NH2]3 (16)
Yield 58%. Brown oil (methylene chloride as eluent). Anal. found (%):
C, 68.50; H, 7.41; N, 13.22. Calc. for C24H30N4O3: C, 68.25; H, 7.11; N,
13.27. IR (cmÀ1): 3421, 3374, 1607, 1500, 1257, 1218, 1039, 843, 735.
1H NMR: d (ppm) 3.11 (t, 6H, 3NH2), 4.12 (t, 6H, 3CH2O), 3.86 (s, b,
6H, 3NH2), 6.68 ꢁ 6.80 (m, 12H, Ar-H).
Preparation of the Schiff Bases: General Procedure
Fifteen mmol of one of the above prepared amines and 45 mmol of a
suitable aldehyde were dissolved in 20 mL of ethanol. The mixture was
refluxed for 3 h. After cooling, the solid product was filtered and washed
with ethanol. Further purification could be performed by recrystallization
from ethanol.
CH3CH2C[CH2O-(C6H4-p)-N ¼ CH-(C6H4-o)-OH]3 (4a)
Yield 96%. Yellow solid, m.p. 118ꢀC (ethanol). Anal. found (%):
C, 75.55; H, 5.83; N, 5.81. Calc. for C45H41N3O6: C, 75.51; H, 5.70; N,
1
5.84. IR (cmÀ1): 3361, 1618, 1577, 1502, 1231, 1022, 821, 747. H NMR:
d (ppm) 1.06 (t, 3H, CH3), 1.90 (q, 2H, CH2C), 4.16 (s, 6H, 3CH2O),
6.90ꢁ7.37 (m, 24H, Ar-H), 8.59 (s, 3H, 3N ¼ CH-). 13.38 (s, 3H, 3ArOH).
CH3CH2C[CH2O-(C6H4-p)-N ¼ CH-Py-2]3 (4b)
Yield 99%. Gray solid, m.p. 108ꢀC (ethanol). Anal. found (%):
C, 74.91; H, 5.93; N, 12.47. Calc. for C42H38N6O3: C, 74.78; H,
5.64; N, 12.46. IR (cmÀ1): 1692, 1603, 1573, 1502, 1218, 1017, 745.
1H NMR: d (ppm) 1.04 (t, 3H, CH3), 1.91 (q, 2H, CH2C), 4.01 (s, 6H,
3CH2O), 6.95 ꢁ 8.17 (m, 24H, Ar-H and Py-H), 9.03 (s, 3H, 3N ¼ CH).

TRIPOD-LIKE COMPOUNDS
1537
CH3CH2C[CH2O-(C6H4-p)-N¼CH-Qui-2]3 (4c)
Yield 98%. Gray solid, m.p. 135ꢀC (ethanol). Anal. found (%):
C, 78.63; H, 5.37; N, 10.07. Calc. for C54H44N6O3: C, 78.64; H, 5.34;
N, 10.19. IR (cmÀ1): 1620, 1590, 1575, 1501, 1237, 1010, 831, 743.
1H NMR: d (ppm) 1.08 (t, 3H, CH3), 1.92 (q, 2H, CH2C), 4.20 (s, 6H,
3CH2O), 7.01 ꢁ 8.38 (m, 30H, Ar-H and Qui-H), 8.85 (s, 3H, 3N ¼ CH).
CH3CH2C[CH2O-(C6H4-o)-N ¼ CH-(C6H4-o)-OH]3 (8a)
Yield 98%. Brown solid, m.p. 117ꢀC(ethanol). Anal. found (%):
C, 75.54; H, 5.81; N, 5.81. Calc. for C45H41N3O6: C, 75.51; H, 5.70;
N, 5.84. IR (cmÀ1): 3340, 1608, 1483, 1455, 1378, 1340, 1008, 742. 1H
NMR: d (ppm) 0.90 (t, 3H, CH3), 1.71 (q, 2H, CH2C), 4.06 (s, 6H,
3CH2O), 6.86 ꢁ 7.65 (m, 24H, Ar-H), 8.91 (s, 3H, 3N ¼ CH), 14.10 (s, b,
3H, 3ArOH).
CH3CH2C[CH2O-(C6H4-o)-N ¼ CH-Py-2]3 (8b)
Yield 97%. Brown solid, m.p. 95ꢀC (ethanol). Anal. found (%):
C, 74.89; H, 5.88; N, 12.41. Calc. for C42H38N6O3: C 74.78; H, 5.64;
1
N, 12.46. IR (cmÀ1): 1617, 1598, 1572, 1224, 1010, 821, 740. H NMR: d
(ppm): 1.06 (t, 3H, CH3), 1.93 (q, 2H, CH2C), 4.17 (s, 6H, 3CH2O),
6.98 ꢁ 8.16 (m, 24H, Ar-H and Py-H), 9.18 (s, 3H, 3N ¼ CH).
CH3CH2C[CH2O-(C6H4-o)-N ¼ CH-Qui-2]3 (8c)
Yield 98%. Brown solid, m.p. 111ꢀC (ethanol). Anal. found (%):
C, 78.61; H, 5.35; N, 10.11. Calc. for C54H44N6O3: C, 78.64; H, 5.34;
N, 10.19. IR (cmÀ1): 1621, 1589, 1574, 1506, 1224, 1021, 830, 741. 1H
NMR: d (ppm) 1.04 (t, 3H, CH3), 1.93 (q, 2H, CH2C), 4.11 (s, 6H,
3CH2O), 7.01 ꢁ 8.31 (m, 30H, Ar-H and Qui-H), 9.01 (s, 3H, 3N ¼ CH).
N[CH2CH2O-(C6H4-p)-N ¼ CH-(C6H4-o)-OH]3 (13a)
Yield 92%. Brown solid, m.p. 112ꢀC (ethanol). Anal. found (%): C,
73.81; H, 5.73; N, 7.55. Calc. for C45H42N4O6: C, 73.57; H, 5.72; N, 7,63.
1
IR(cmÀ1): 3289, 1620, 1601, 1574, 1234, 1020, 822, 745. H NMR: d (ppm)

1538
LU ET AL.
3.10 (t, 6H, 3NCH2), 4.13 (t, 6H, 3CH2O), 6.50 ꢁ 7.60 (m, 24H,
Ar-H), 8.91 (s, 3H, 3N¼CH), 13.24 (s, 3H, 3Ar-OH).
N[CH2CH2O-(C6H4-p)-N ¼ CH-Py-2]3 (13b)
Yield 95%. Brown solid, m.p. 108ꢀC (ethanol). Anal. found (%):
C, 73.15; H, 5.69; N, 12.01. Calc. for C42H39N7O3: C, 73.15; H, 5.66;
1
N, 12.19. IR (cmÀ1): 1621, 1608, 1574, 1506, 1220, 1014, 739. H NMR: d
(ppm) 3.13 (t, 6H, 3NCH2), 4.15 (t, 6H, 3CH2O), 6.79 ꢁ 8.03 (m, 24H, Ar-H
and Py-H), 9.11(s, 3H, 3N ¼ CH).
N[CH2CH2O-(C6H4-p)-N ¼ CH-Qui-2]3 (13c)
Yield 98%. Brown solid, m.p. 100ꢀC (ethanol). Anal. found (%):
C, 77.47; H, 5.38; N, 11.54. Calc. for C54H45N7O3: C, 77.23; H, 5.36;
1
11.68. IR (cmÀ1): 1618, 1597, 1569, 1504, 1220, 1011, 834, 743. H NMR:
d (ppm) 3.11(t, 6H, 3NCH2), 4.17(t, 6H, 3CH2O), 6.98 ꢁ 8.31 (m, 30H, Ar-
H and Qui-H), 9.05(s, 3H, 3N ¼ CH).
N[CH2CH2O-(C6H4-o)-N ¼ CH-(C6H4-o)-OH]3 (17a)
Yield 88%. Brown solid, m.p. 106ꢀC (ethanol). Anal. found (%):
C, 73.43; H, 5.96; N, 7.58. Calc. for C45H42N4O6: C, 73.57; H, 5.72, N,
1
7.63. IR (cmÀ1): 3338, 1610, 1507, 1485, 1378, 1340, 1010, 740. H NMR:
d (ppm) 3.14 (t, 6H, 3NCH2), 4.13 (t, 6H, 3CH2O), 6.97 ꢁ 7.41 (m, 24H,
Ar-H), 8.71 (s, 3h, 3N ¼ CH), 13.52 (s, 3H, 3Ar-OH).
N[CH2CH2O-(C6H4-o)-N ¼ CH-Py-2]3 (17b)
Yield 90%. Brown solid, m.p. 101ꢀC (ethanol). Anal. found (%):
C, 73.29; H, 5.65; N, 12.11. Calc. for C42H39N7O3: C, 73.15; H,
5.66; N, 12.19. IR (cmÀ1): 1620, 1602, 1573, 1223, 1021, 822, 744.
1H NMR: d (ppm) 3.13 (t, 6H, 3NCH2), 4.08 (t, 3H, 3CH2O), 7.01 ꢁ 8.10
(m, 24H, Ar-H and Py-H), 9.35 (s, 3H, 3N ¼ CH).
N[CH2CH2O-(C6H4-o)-N ¼ CH-Qui-2]3 (17c)
Yield 93%. Brown solid, m.p. 118ꢀC (ethanol). Anal. found (%):
C, 77.31; H, 5.35; N, 11.70. Calc. for C54H45N7O3: C, 77.23; H, 5.36; N,

TRIPOD-LIKE COMPOUNDS
1539
1
11.68. IR (cmÀ1): 1618, 1579, 1562, 1501, 1242, 1020, 833, 743. H NMR: d
(ppm) 3.12 (t, 6H, 3NCH2), 4.16 (t, 6H, 3CH2O), 6.90 ꢁ 8.41 (m, 30H, Ar-H
and Qui-2H), 9.17 (s, 3H, 3N ¼ CH).
Preparation of Salicyl Amide: General Procedure
To a solution of 4 mmol of salicylic acid in 20 mL of chlorobenzene
was added successively 1.5 mmol of phosphorus trichloride and 1 mmol of
the above prepared amine. The mixture was heated to reflux for 5 h with
stirring. Chlorobenzene was distilled off. The residue was washed with a hot
dilute solution of sodium hydrocarbonate and water. The resulting solid was
recrystallized from ethanol. Further purification was carried out through
chromatography with chloroform as eluent.
CH3CH2C [CH2O-(C6H4-p)-NHCO-(C6H4-o)-OH]3 (5)
Yield 78%. Gray solid, m.p. 90ꢀC. Anal. found (%): C, 70.41; H, 5.69;
N, 5.47. Calc. for C45H41N3O9: C, 70.40; H, 5.35; N, 5.48. IR (cmÀ1): 3401,
1638, 1600, 1507, 1220, 1022, 820, 743. 1H NMR: d (ppm) 1.07(t, 3H, CH3),
1.90(q, 2H, CH2C), 4.19(s, 6H, 3CH2O), 7.00 ꢁ 8.00(m, 24H, Ar-H), 10.45
(s, 3H, 3NH), 12.11(s, 3H, 3Ar-OH).
CH3CH2C[CH2O-(C6H4-o)-NHCO-(C6H4-o)-OH]3 (9)
Yield 79%. Gray solid, m.p. 93ꢀC. Anal. found (%):C, 70.42; H, 5.67;
N, 5.44. Calc. for C45H41N3O9: C, 70.40; H, 5.35; N, 5.48. IR (cmÀ1):
1
3403, 1647, 1602, 1511, 1220, 1023, 822, 741. H NMR: d (ppm) 0.89 (t,
3H, CH3), 1.88 (q, 2H,CH2C), 4.21 (s, 6H, 3CH2O), 6.98 ꢁ 7.88 (m, 24H,
Ar-H), 10.39 (s, 3H, 3NH), 13.87 (s, 3H, 3Ar-OH).
N[CH2CH2O-(C6H4-p)-NHCO-(C6H4-o)-OH]3 (14)
Yield 70%. Gray solid, m.p. 101ꢀC. Anal. found (%): C, 69.11;
H, 5.40; N, 7.12. Calc. for C45H42N4O9: C, 69.05; H, 5.37; N, 7.16. IR
1
(cmÀ1): 3396, 1641, 1601, 1507,1222, 1020, 831, 742. H NMR: d (ppm)
3.80 (t, 6H, 3NCH2), 4.48 (t, 6H, 3CH2O), 6.93 ꢁ 8.01 (m, 24H, Ar-H),
10.37 (s, 3H, 3NH), 11.99 (s, 3H, 3Ar-OH).

1540
LU ET AL.
N[CH2CH2O-(C6H4-o)-NHCO-(C6H4-o)-OH]3 (18)
Yield 70%. Gray solid, m.p. 96ꢀC. Anal. found (%): C, 68.99; H, 5.39;
N, 7.17. Calc. for C45H42N4O9: C, 69.05; H, 5.37; N, 7.16. IR (cmÀ1): 3400,
1
1638, 1605, 1521, 1224, 1022, 822, 739. H NMR: d (ppm) 3.11 (t, 6H,
3NCH2), 4.10 (t, 6H, 3CH2O), 6.97 ꢁ 7.91 (m, 24H, Ar-H), 10.12 (s, 3H,
3NH), 13.57 (s, 3H, 3Ar-OH).
ACKNOWLEDGMENTS
This work was financed by the National Natural Science Foundation
of China (No. 29871025).
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Received in the USA August 9, 2000