Synthesis of new multibenzo oxygen-sulfur donor macrocycles containing lactams at room temperature

Article abstract of DOI:10.1080/10426500902994320

Some new oxygen-sulfur, multibenzo macrocyclic ligands containing amide groups have been prepared using the macrocyclization process with the reaction of 2,2'-thiobis-[4-methyl(2-aminophenoxy)phenyl ether] as a symmetrical diamine with appropriate dicarboxylicacid dichlorides in moderate yields. This macrocyclization led to the formation of di- and tetramide macrocycles. These reactions were routinely carried out at ambient temperature in CH2Cl2 as solvent in high dilution without template effect conditions. It is found that sulfur the atom affects the rigidity of the macrocycles and diastereotopicity of nuclei in the ring of these series of macrocyclic compounds.

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Synthesis of New Multibenzo
Oxygen–Sulfur Donor Macrocycles
Containing Lactams at Room
Temperature
Abbas Shockravi a , Mahdieh Sadeghpour b c , Masoomeh Zakeri a ,
Ebrahim Abouzari-Lotf a & Abolfazl Olyaei d
a Faculty of Chemistry , Tarbiat Moallem University , Tehran, Iran
b Department of Chemistry , Islamic Azad University, Takestan
Branch , Qazvin, Iran
c Islamic Azad University , Takestan Branch , Qazvin, Iran, Member
of Young Researchers Club
d Department of Chemistry , Payame Noor University , Qazvin, Iran
Published online: 23 Mar 2010.
To cite this article: Abbas Shockravi , Mahdieh Sadeghpour , Masoomeh Zakeri , Ebrahim Abouzari-
Lotf & Abolfazl Olyaei (2010) Synthesis of New Multibenzo Oxygen–Sulfur Donor Macrocycles
Containing Lactams at Room Temperature, Phosphorus, Sulfur, and Silicon and the Related Elements,
185:4, 808-815, DOI: 10.1080/10426500902994320
To link to this article: http://dx.doi.org/10.1080/10426500902994320
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Phosphorus, Sulfur, and Silicon, 185:808–815, 2010
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500902994320
SYNTHESIS OF NEW MULTIBENZO OXYGEN–SULFUR
DONOR MACROCYCLES CONTAINING LACTAMS AT
ROOM TEMPERATURE
Abbas Shockravi,1 Mahdieh Sadeghpour,2,3 Masoomeh Zakeri,1
Ebrahim Abouzari-Lotf,1 and Abolfazl Olyaei4
1Faculty of Chemistry, Tarbiat Moallem University, Tehran, Iran
2Department of Chemistry, Islamic Azad University, Takestan Branch, Qazvin, Iran
3Islamic Azad University, Takestan Branch, Qazvin, Iran, Member of Young
Researchers Club
4Department of Chemistry, Payame Noor University, Qazvin, Iran
Some new oxygen–sulfur, multibenzo macrocyclic ligands containing amide groups have
been prepared using the macrocyclization process with the reaction of 2,2ꢀ-thiobis-[4-
methyl(2-aminophenoxy)phenyl ether] as a symmetrical diamine with appropriate dicar-
boxylicacid dichlorides in moderate yields. This macrocyclization led to the formation of di-
and tetramide macrocycles. These reactions were routinely carried out at ambient tempera-
ture in CH2Cl2 as solvent in high dilution without template effect conditions. It is found that
sulfur the atom affects the rigidity of the macrocycles and diastereotopicity of nuclei in the
ring of these series of macrocyclic compounds.
Keywords Diamide; diamine; dicarboxylic acid dichloride; lactam; macrocycle
INTRODUCTION
The increasing interest in the molecular recognition properties of naturally occurring
macrocycles has attracted much attention in the design and synthesis of new cyclic polyaza-
and polyoxa macrocycles.1 Among others, macrocyclic amides are used as host molecules.
They act as hydrogen-bond donors and hydrogen-bond acceptors, and can form complexes
with neutral molecules of biological interest.2 Macrocyclic diamides and corresponding
aza crown compounds have gained a great deal of attention due to their wide applications
in chemistry, analysis and microanalysis, metal separation and transport, molecular recog-
nition, medical and industrial uses, biophysics, catalysis, enzyme mimics, sensoring and
switching agriculture, and ecology.3 There have been recent developments in the use of par-
ticular macrocyclic amides for metal ion discrimination. For example, diamide-containing
macrocycles have been reported to exhibit selectivity for lithium which is superior to that
reported for 14-crown-4. In the other study, a 14-membered ligand ring containing two
amides and two sulfur donor groups was shown to be selective for Pd(II) and Pt(II) over
Received 23 January 2009; accepted 24 April 2009.
We thank the Research Council of the Tarbiat Moallem University for financial support. We wish also to
thank Prof. R. Gleiter and Ms. Birgit Esser from Heidelberg, Germany, for FAB-mass analysis of macrocycle 3.
Address correspondence to Abbas Shockravi, Faculty of Chemistry, Tarbiat Moallem University, Mofatteh
Ave., No 49, Postal Code 15614, Tehran, Iran. E-mail: Abbas shockravi@yahoo.co.uk
808

MULTIBENZO OXYGEN–SULFUR DONOR MACROCYCLES
809
Co(II), Ni(II), and Cu(II).4 In particular, the use of thia-containing macrocycles as building
blocks in such systems yields the potential of binding soft metals in either the ligand’s
endo- or exocyclic modes; in particular exo-coordination has now been well documented
for such sulfur-containing ligand systems.5 Macrocyclic diamides are also valuable inter-
mediates for the preparation of azacrown compounds and more complicated ligands such
as cryptands and cryptohemispherands, which can be functionalized by additional ligating
centers including chromogenic and proton ionizable groups.6
There are a variety of synthesis methods for macrocyclic diamides such as high
dilution techniques,7 the route based on the template effect,8 and high pressure approach.9
In addition, they are prepared by various procedures including reaction of α, γ -diester
and different diester derivatives,10 dicarboxylic acid diesters, diacid dichloride,11,12 bis(α-
chloroamide) compounds,13 and activated carboxylic acids14 with various diamines.
In our previous work, we have described the synthesis of new dibenzosulfide
and dibenzosulfoxide amidic macrocycle compounds using dicarboxylic acid diester
and diacid dichloride methods.15,16 In this article, we report the synthesis of series of
new multibenzooxathia macrocyclic amides. For this purpose, 2,2ꢁ-thiobis-[4-methyl(2-
aminophenoxy)phenyl ether] (1)17 was reacted with dicarboxylic acid dichlorides in dry
CH2Cl2 solvent at ambient conditions, which afforded new multibenzo oxygen-sulfur donor
macrocycles containing lactams. It should be noted that the diamine 1 was synthesized by
our research team previously and was introduced as a novel complexing agent for Cd2+ and
Co2+ with no significant interference from other ions such as Zn2+ being observed.17 This
selectivity evidence in the complexation behavior of diamine 1 encouraged us to synthesize
the corresponding amidic macrocyclic derivatives. The complexation of these macrocycles
with different metal ions is under study in our laboratory.
RESULTS AND DISCUSSION
The reactions of dicarbonyl compounds with diamines are much more complicated
and can produce a wide spectrum of products. As the model reaction, we initially examined
the reaction of bisamine 1 with oxalyl chloride in dry CH2Cl2 as solvent in high dilution con-
ditions in the presence of triethyl amine at room temperature. Thin layer-chromatography
(TLC) indicated that a period of at least 20 h was needed for the reaction to be completed.
TLC also showed that the mixture consisted of two products. These products were sepa-
rated by column chromatography on silica gel using hexane/EtOAc (4:1) as eluent to afford
tetrabenzodioxathiadiamide 2 and octabenzotetraoxadithiatetramide 3 with 40% and 38%
yield, respectively (Scheme 1).
O
O
O
NH2
O
H2N
O
NH
HN
HN
HN
O
H3C
CH3
CH3
O
NH
NH
O
O
O
O
S
S
+
S
S
CH2Cl2 / r.t
O
H3C
O
O
O
O
CH3
CH3
CH3
CH3
Cl
Cl
1
2
[1+1]
3
[2+2]
Scheme 1 Synthesis of [1+1] and [2+2]-condensation products 2 and 3.

810
A. SHOCKRAVI ET AL.
Identification of compounds 2 and 3 was made by elemental analysis, mass spectra,
and NMR spectroscopy. The 1H NMR spectra of compounds 2 and 3 showed a sharp singlet
for the methyl groups at δ 2.1 and 2.3 ppm, and amide protons appeared as singlet signal at
about δ 9.0 and 9.6 ppm, respectively. The other protons showed in the aromatic regions.
The 13C NMR spectra were identified for the compounds 2 and 3. The IR spectra revealed
an amide absorption bond at about 1680 cm−1. FAB mass spectra confirmed the mass
and proposed structures of compounds 2 and 3 as 15-membered macrocyclic diamide and
30-membered macrocyclic tetramide, respectively. These compounds were obtained from
[1+1] and [2+2]-condensation of diamine and oxalyl chloride via regular macrocyclization
and dimerization, respectively.
We also examined condensation of symmetrical diamine 1 with succinyl chloride in
the same reaction conditions. In this reaction, [1+1] condensation macrocyclic diamide
1
4 was obtained in 40% yield. The H NMR spectrum showed two singlet signals in the
aliphatic regions for methyl and methylene protons at δ 2.29 and 2.48 ppm, respectively,
and a sharp singlet signal appeared at δ 8.07 ppm for NH. The 13C NMR spectrum revealed
two signals for above methyl and methylene carbon at δ 20.83 and 32.52 ppm, respectively.
Mass spectrum showed the molecular ion peak at m/z 510, which also is in agreement with
the proposed structure (Scheme 2).
O
O
NH2
O
H2N
O
NH
O
HN
O
O
CH2Cl2 / r.t
S
Cl
S
Cl
+
O
CH3
CH3
CH3
CH3
1
4 [1+1]
Scheme 2 [1+1]-Macrocyclization of diamine 1 and succinyl chloride.
In the macrocyclization reaction of diamine 1 with 2,2ꢁ-dithiodibenzoicacid dichlo-
ride (5), only regular macrocyclization ([1+1]) occurred. In this reaction, a 21-membered
macrocyclic diamide 7 (hexabenzodioxatrithiadiamide) was isolated in 60% yield as the
main product (Scheme 3). The interesting point in compound 7 was the absorption of two
1
types of methyl signals at δ 2.16 and 2.26 ppm in the H NMR spectrum. The extent of
rigidity of these macrocycles affects the methyl absorption regions. However, the macrocy-
cles are twisted due to the repulsion effects of nonbonding electron pairs on sulfur, nitrogen,
oxygen atoms and carbonyl groups in the cavity, and the intramolecular H-bondings cause
rigidity in the macrocycles. Also, the repulsion between hydrogens of phenyl groups on
the crown help the deformation in this part of the molecule. As an example, the rigidity
of macrocycle 7 was confirmed by the absorption of two methyl groups at δ 20.56 and
20.70 ppm in the 13C NMR and 38 types of carbons in aromatic regions. Observation of a
molecular ion peak in the mass spectrum confirmed the molecular structure.
In another experiment, macrocyclization of diamine 1 with 1,2-bis(2-chlorocarbonyl
ethoxy)benzene (6) was investigated under the same reaction conditions. This reaction led
to the formation of [1+1] condensation macrocycle 8 (pentabenzotetraoxathiadiamide) in
65% yield as the only product (Scheme 4).

MULTIBENZO OXYGEN–SULFUR DONOR MACROCYCLES
811
O
O
S S
NH2
O
H2N
O
NH
O
HN
O
O
Cl
Cl
O
S
CH2Cl2 / r.t
S
S
+
S
CH3
CH3
CH3
CH3
5
1
7 [1+1]
Scheme 3 Synthesis of [1+1]-macrocycle 7.
O
O
NH2
O
H2N
O
O
O
NH
O
HN
OCH2CH2COCl
CH2Cl2 / r.t
S
+
O
OCH2CH2COCl
S
CH3
CH3
1
6
CH3
CH3
8 [1+1]
Scheme 4 Cyclocondensation of diamine 1 with 1,2-bis(2-chlorocarbonyl ethoxy)benzene 6.
It should be noted that the meta and para isomers of compound 6 were examined for
a similar macrocyclization process, but the corresponding macrocycles were not obtained.
1
Identification of compound 8 was carried out on the basis of spectroscopic data. The H
NMR spectra of compound 8 show a sharp singlet for two methyl groups at about δ 2.2 ppm.
These observations indicated that the rigidity is reduced in this macrocycle compared to
macrocycle 7. This behavior may be because of reduction of the intramolecular H-bonding
density and more flexibility in the cavity of this macrocycle compared to macrocycle 7.
Methylene protons revealed two triplets at about δ 2.7 and 4.2 ppm, and NH protons showed
a singlet signal at about δ 8.6 ppm (Figure 1). Again, the observation of a molecular ion
peak confirmed the molecular structure.
In conclusion, we have described the synthesis of a new multibenzo macrocyclic
containing sulfur, oxygen, and lactam functional groups. In this process, the reaction of
diamine 1 with oxalyl chloride give [1+1] and [2+2] condensations, with succinyl chloride,
2,2ꢁ-dithiodibenzoicacid dichloride (5), and 1,2-bis(2-chlorocarbonyl ethoxy)benzene (6)
afford [1+1] condensation macrocyclic diamides, respectively. The flexibility and rigidity
of this series of macrocycles are confirmed by spectroscopic means in this work. The
repulsion between the hydrogens of phenyl groups in the crown part of the ring and the
tetrahedral character of sulfide atoms affects the rigidity of the cavities significantly.

812

MULTIBENZO OXYGEN–SULFUR DONOR MACROCYCLES
813
EXPERIMENTAL
All commercially available chemicals and reagents were used without further purifi-
cation. Melting points (uncorrected) were determined by an Electrothermal Engineering
LTD 9100 apparatus. IR spectra were recorded on a Perkin-Elmer model 543, the 1H and 13
C
NMR spectra were obtained using a Bruker Avance DRX 300 apparatus at 298 K. Chemi-
cal shifts (δ) are reported in ppm and are referenced to the NMR solvent peak. Elemental
analyses were carried out by a CHN-O-Rapid Heraeus elemental analyzer (Wellesley, MA).
Mass spectra of the products were obtained with an HP (Agilent technologies) 5937 Mass
Selective Detector. Also the FAB-mass spectrum of compound 3 was obtained by electron
ionization Varian Incos 50 and JEOLJMS-700 and MULDI spectra Bruker Bifleα. CH2Cl2
was dried over P2O5 and then distilled from CaH2. 2,2ꢁ-Dithiodibenzoic acid dichloride
(5) was obtained by the reaction of 2,2ꢁ-dithiodibenzoic acid and oxalyl chloride in the
presence of catalytic amounts of DMF in CH2Cl218 and identified with spectroscopic anal-
ysis. Compound 6 was obtained by the reaction of 1,2-bis(2-carboxyethoxy)benzene19 with
oxalyl chloride in the presence of catalytic amounts of DMF in CH2Cl2 and identified with
spectroscopic analysis.
General Procedure for the Preparation of Macrocyclic Diamides 2–4, 7–8
A solution of diacid dichloride (2 mmol) in dry dichloromethane (50 mL) was added
dropwise to a vigorously stirred solution of diamine 1 (2 mmol) in the same solvent (50 mL)
containing triethylamine (4 mmol) for 30 min at 0–5◦C. The mixture was stirred for 20 h at
room temperature. The solvent was then removed under reduced pressure to give a crude
product, which was purified by column chromatography on silica gel 60 using the proper
eluent solvent.
2,21-Dimethyltetrabenzo[b,e,h,n][1,7]dioxa[4]thia[10,13]diazacyclopen-
tadecin-11,12-(10H,13H)-dione (2). This compound was purified by column chro-
matography on silica gel using hexane:EtOAc (4:1) as eluent to afford a white solid
product, mp 254–255◦C; IR (potassium bromide): 3332, 3294, 3066, 2929, 1678, 1602,
1
1511, 1440, 1446, 1251, 1226, 746 cm−1; H NMR (300 MHz, CDCl3): δ 2.12 (s, 6H,
CH3), 6.81–7.65 (m, 14H, Ar-H), 9.00 (s, 2H, NH); 13C NMR (75 MHz, CDCl3): δ 159.23,
152.44, 148.29, 134.12, 132.88, 128.92, 127.53, 126.98, 125.50, 124.46, 124.07, 119.54,
117.53, 20.55 ppm; ms: m/z 482 [M]+, 483 [M+1]+, 484 [M+2]+, 485 [M+3]+, 227,
197, 152, 91; Anal. Calcd. For C28H22N2O4S: C, 69.71; H, 4.56; N, 5.81. Found: C, 69.65;
H, 4.60; N, 5.80.
2,21,25,44-Tetramethyloctabenzo[b,e,h,n,q,t,w,c1][1,7,16,22]tetraoxa[4,
19]dithia[10,13,25,28]tetraazacyclotriacontin-11,12,26,27-(10H,13H,25H,28H)-
tetraone (3). This compound was purified by column chromatography on silica gel
using hexane:EtOAc (4:1) as eluent to afford a white solid product, mp 350–353◦C; IR
(potassium bromide): 3360, 3322, 3025, 2927, 1689, 1602, 1524, 1469, 1446, 1250, 1228,
751 cm−1; 1H NMR (300 MHz, CDCl3): δ 2.33 (s, 12H, CH3), 6.61–8.38 (m, 28H, Ar-H)
9.62 (s, 4H, NH); 13C NMR (75 MHz, CDCl3): δ 157.57, 152.30, 147.23, 134.84, 133.81,
129.65, 127.82, 126.25, 124.73, 123.30, 121.02, 120.57, 116.51, 20.81 ppm; MS-FAB:
m/z 964 [M]+, 965 [M+1]+, 966 [M+2]+, 967 [M+3]+, 937, 533, 482, 460, 455, 307,
228, 197; Anal. Calcd. For C56H44N4O8S2: C, 69.71; H, 4.56; N, 5.81. Found: C, 69.68;
H, 4.52; N, 5.84.

814
A. SHOCKRAVI ET AL.
2,23-Dimethyl-12,13-dihydrotetrabenzo[b,e,h,p][1,7]dioxa[4]thia[10,15]
diazacycloheptadecin-11,14-(10H,15H)-dione (4). This compound was purified by
column chromatography on silica gel using hexane:EtOAc (5:1) as eluent to afford a white
solid product, mp 242–244◦C; IR (potassium bromide): 3418, 3349, 2944, 2926, 1682,
1
1600, 1520, 1473, 1442, 1244, 1225, 751 cm−1; H NMR (300 MHz, CDCl3): δ 2.29
(s, 6H, CH3), 2.48 (s, 4H, CH2), 6.66–7.27 and 8.28 (m, 14H, Ar-H), 8.07 (s, 2H, NH);
13C NMR (75 MHz, CDCl3): δ 170.43, 152.32, 146.08, 134.90, 133.28, 129.82, 129.27,
126.90, 125.70, 123.72, 121.23, 119.91, 116.81, 32.52, 20.83 ppm; ms: m/z 510 [M]+, 511
[M+1]+, 512 [M+2]+, 513 [M+3]+, 214, 197, 77, 55; Anal. Calcd. For C30H26N2O4S: C,
70.58; H, 5.10; N, 5.49. Found: C, 70.52; H, 5.14; N, 5.44.
2,31-Dimethylhexabenzo[b,e,h,l,p,t][1,7]dioxa[4,14,15]trithia[10,19]dia-
zacyclohenicosin-11,118-(10H,19H)-dione (7). This compound was purified by
column chromatography on silica gel using hexane:EtOAc (3:1) as eluent to afford a white
solid product, mp 170–171◦C; IR (potassium bromide): 3425, 3350, 3058, 1669, 1604,
1
1519, 1479, 1444, 1324, 1229, 745 cm−1; H NMR (300 MHz, CDCl3): δ 2.16 (s, 3H,
CH3), 2.26 (s, 3H, CH3), 6.62–7.35 (m, 22H, Ar-H), 8.50 (br, 2H, NH); 13C NMR (75
MHz, CDCl3): δ 165.35, 165.20, 153.52, 151.80, 146.22, 139.19, 138.31, 138.21, 135.27,
133.39, 133.14, 133.02, 132.80, 132.57, 131.66, 130.07, 129.86, 129.28, 128.50, 127.33,
127.05, 126.90, 126.02, 124.64, 124.28, 123.47, 120.79, 120.50, 120.46, 120.02, 119.61,
118.54, 118.32, 116.90, 116.41, 116.30, 115.82, 115.65, 20.70, 20.56 ppm; ms: m/z 698
[M]+, 699 [M+1]+, 700 [M+2]+, 701 [M+3]+, 562, 471, 428, 349, 228, 214, 197, 137;
Anal. Calcd. For C40H30N2O4S3: C, 68.76; H, 4.29; N, 4.01. Found: C, 68.80; H, 4.22; N,
4.07.
2,31-Dimethyl-12,13,18,19-tetrahydropentabenzo[b,e,h,o,v][1,7,14,17]-
tetraoxa[4]thia[10,21]diazacyclotricasin-11,20-(10H,21H)-dione (8). This com-
pound was purified by column chromatography on silica gel using hexane:EtOAc (3:1)
as eluent to afford a white solid product, mp 130–132◦C; IR (potassium bromide): 3420,
1
3348, 3063, 2925, 1692, 1603, 1526, 1479, 1449, 1254, 747 cm−1; H NMR (300 MHz,
acetone-d6): δ 2.27 (s, 6H, CH3), 2.72–2.76 (t, 4H, J = 5.8 Hz, CH2), 4.20–4.24 (t, 4H,
J = 5.8 Hz, CH2), 6.80–8.38 (m, 18H, Ar-H), 8.64 (s, 2H, NH); 13C NMR (75 MHz,
acetone-d6): δ 169.76, 153.48, 150.24, 135.59, 133.75, 130.71, 125.64, 124.53, 124.34,
123.53, 122.02, 120.25, 118.36, 117.88, 117.51, 116.05, 66.56, 38.12, 20.65 ppm; ms: m/z
646 [M]+, 647 [M+1]+, 648 [M+2]+, 649 [M+3]+, 536, 482, 391, 319, 252, 228, 214,
197, 146, 110, 55; Anal. Calcd. For C38H34N2O6S: C, 70.58; H, 5.26; N, 4.33. Found: C,
70.52; H, 5.25; N, 4.36.
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