Synthesis of new aza thia crowns under microwave irradiation

Article abstract of DOI:10.1080/17415993.2012.674131

Some new aza thia crowns were prepared. A new diester was first prepared from the reaction of α, α′-bis(bromomethyl) benzene and methylthioglycolate. Aza crowns were synthesized from the reactions of this diester and diamines (ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, and diethylenetriamine) in refluxing methanol (conventional heating) and under microwave (MW) irradiation. Based on the yields of aza crowns under these two conditions, MW irradiation is the better medium for these syntheses.

Full text of DOI:10.1080/17415993.2012.674131

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Synthesis of new aza thia crowns under
microwave irradiation
Esmael Rostami a , Marziyh Ghaedi a , Masume Zangooei a &
Abdolkarim Zare a
a Department of Chemistry, Payame Noor University, PO Box
19395-3697, Tehran, Iran
Version of record first published: 04 May 2012.
To cite this article: Esmael Rostami, Marziyh Ghaedi, Masume Zangooei & Abdolkarim Zare (2012):
Synthesis of new aza thia crowns under microwave irradiation, Journal of Sulfur Chemistry, 33:3,
327-333
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Journal of Sulfur Chemistry
Vol. 33, No. 3, June 2012, 327–333
Synthesis of new aza thia crowns under microwave irradiation
Esmael Rostami*, Marziyh Ghaedi, Masume Zangooei and Abdolkarim Zare
Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran
(Received 16 January 2012; final version received 4 March 2012)
Some new aza thia crowns were prepared. A new diester was first prepared from the reaction of α, αꢀ-
bis(bromomethyl)benzeneandmethylthioglycolate.Azacrownsweresynthesizedfromthereactionsofthis
diester and diamines (ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, and
diethylenetriamine) in refluxing methanol (conventional heating) and under microwave (MW) irradiation.
Based on the yields of aza crowns under these two conditions, MW irradiation is the better medium for
these syntheses.
Keywords: aza thia crown; synthesis; α, αꢀ-bis (bromomethyl) benzene; methylthioglycolate; receptor;
macrocycle
1. Introduction
Synthetic macrocycles have been known for over 75 years, although Pedersen published in 1967
a very important and pioneering advance in this area (1). The publications of Pedersen and
other research groups provided the foundation for host–guest chemistry and, in recent years,
supramolecular chemistry (2). Since the appearance of these seminal publications, the number of
macrocyclic compounds has increased markedly from year to year (3). The “hard” ether–oxygen-
containing macrocycles show a binding preference toward “hard” alkali and alkaline earth metal
cations, but the incorporation of “soft” sulfide or amine linkages shifts their preference toward
“soft” heavy metal cations (4). It has been demonstrated that macrocyclic ligands containing
nitrogen–sulfur donor atoms can behave as highly selective complexing agents for transition
metal cations (5–7). The aza ligands are more selective against hard ions, whereas the thia ligands
preferentially bind soft ions. Combining different donor atoms in one ring system can enhance
*Corresponding author: Email: esmrostami@yahoo.com
ISSN 1741-5993 print/ISSN 1741-6000 online
© 2012 Taylor & Francis
http://dx.doi.org/10.1080/17415993.2012.674131
http://www.tandfonline.com

328 E. Rostami et al.
selectivity. Therefore, nitrogen–sulfur macrocycles having different ring sizes or heteroatom
placements have been prepared and their complexation properties have been investigated with
various metal cations (8–11).
There are several efficient reaction routes for the synthesis of crown ethers and aza crowns,
such as high dilution conditions, fast additions, and template synthesis (12). In addition, the
reaction of diesters and diamines at room temperature (13) under reflux conditions (14) are two
important and common methods for the synthesis of these compounds. As part of our inter-
est in the modification of aza crowns and our goal of producing aza crowns in higher yields
under milder reaction conditions and in shorter reaction times, we introduce here a new experi-
mental protocol in addition to those mentioned above that utilizes microwave (MW) irradiation
conditions (15). MW-assisted organic synthesis has been widely utilized in recent years for
the formation of a variety of carbon–carbon and carbon heteroatom bonds, which usually lead
to remarkable decreases in reaction times, enhancement in yields, easier workup, and better
regioselectivity (16).
This report is a continuation of our previous interest in the synthesis of aza crowns (17–19).
The use of MW irradiation for the synthesis of new aza thia crowns dramatically improves the
experimental ease of production of these compounds. New investigations to explore the chemistry
of these new receptors are underway.
2. Results and discussion
In this study, diester (2) was prepared from the reaction of 1 and methylthioglycolate in
acetonitrile in the presence of catalytic amounts of dimethyl formamide (DMF) at room tem-
perature (Scheme 1). Aza crowns (3–7) were prepared using two different reaction conditions,
i.e. refluxing methanol (conventional heating) and under MW irradiation using ethyleneglycol as
solvent (Scheme 1).
Scheme 1. Synthesis of aza thia crowns (3–7).
The synthesis of these aza crowns (3–7) using conventional heating is a low-yield process but the
synthesis under MW irradiation is an excellent reaction route as shown in Table 1. One proposed

Journal of Sulfur Chemistry 329
Table 1. The synthesis of aza crowns under conventional heating
(reflux) and under MW irradiation.
Aza crown
Yield (%)a (MW)
Yield (%)a (reflux)
3
4
5
6
7
88
91
86
83
74
19
14
16
13
9
Note: aIsolated yield.
approach to explain these results is based on the competition between inter and intramolecular
hydrogen bonding (Scheme 2) (19, 20). Intramolecular hydrogen bonding stabilizes the cyclic
intermediates. Intramolecular hydrogen bonding is stronger than intermolecular hydrogen bond-
ing at elevated temperatures and therefore would also be expected to be stronger under MW
irradiation conditions (21). Consequently, intramolecular hydrogen bonding favors the cyclic
intermediate and the synthesis of aza crowns under MW irradiations is a high-yield process
(Scheme 2).
3. Conclusions
The synthesis of aza crowns under MW irradiation is a more convenient route than conventional
heating. Macrocyclization processes are preferred relative to oligomerization or polymerization
under MW irradiation conditions and the yields of macrocycles are high. Under conventional
heating, the oligomerization route is more important than the macrocyclization route and linear
products are produced in high yields.
4. Experimental
The reactions were carried out in an efficient hood. All the materials were purchased from Merck,
Fluka, Acros Organics, and Aldrich chemical companies. Acetonitrile and methanol were dis-
tilled and stored over molecular sieves. DMF was distilled over molecular sieves under reduced
pressure and also stored over molecular sieves. Merck silica gel 40 was used for column chro-
matography. Merck silica gel 60 F254 TLC (thin layer chromatography) plates were used for
TLC. The melting points (uncorrected) were measured with an Electrothermal Engineering LTD
9100 apparatus. Elemental analyses were performed using a CHN–O– Rapid Heraeus elemental
analyzer. IR spectra were measured on Perkin-Elmer model 543 and FT-IR BRUKER spectrom-
1
eters. The H NMR and 13C NMR spectra for 2 were obtained using a BRUKER AVANCE
DPX 300 MHz 1H NMR and 75 MHz 13C NMR instrument. For the other compounds, 1H NMR
and 13C NMR spectra were obtained using a BRUKER AVANCE DRX 500 MHz 1H NMR and
125 MHz 13C NMR instrument. Mass spectra were obtained with a 1000 EX model Shimadzu
GC-MS-QP.
A Milestone MicroSYNTH system multi-mode platform equipped with a magnetic stirring plate
was used for the synthesis. We also used high-pressure vessels with teflon inserts with 100 ml
volumes with the max pressure capability of 1450 psi and max temperature capacity of 300 ◦C.
The system has two magnetrons that together deliver a maximum power output of 1000W. The
power supply of the magnetron is pulsed. Temperature is controlled with an internal fiber optic
probe in a control reference vessel.

330 E. Rostami et al.
Scheme 2. Proposed mechanism for the synthesis of aza crowns.
4.1. Synthesis of 1,2-di(5-oxa-4-oxo-2-thiahexyl) benzene (2)
To acetonitrile (50 ml) and catalytic amounts of DMF were added 1 (2 mmol, 0.92 g), potassium
carbonate (4 mmol, 0.56 g) and methylthioglycolate (4 mmol, 0.40 ml) at room temperature. The
mixture was stirred at room temperature for 12 h. After completion of the reaction (monitored by
TLC), water was added and the resulting mixture was extracted with chloroform (3 × 100 ml),
washed with water (2 × 100 ml), dried (Na2SO4) and evaporated to obtain a colorless oil. The
resultingcrudeoilwaspurifiedbydryflashchromatographyusing n-hexane/ethylacetate aseluent.
Then, the resulting mixture was evaporated under reduced pressure to afford 2 in 96% yield as
=
a colorless oil; IR (KBr): 2963, 2871, 2656, 1695 (C O), 1586, 1463, 1408, 1322, 1274, 1162,
1
1043, 926 cm−1; H NMR (300 MHz, CDCl3): δ = 3.14 (s, 4H, CH2), 4.72 (s, 6H, CH3), 4.02
(s, 4H, CH2), 7.20–7.24 (m, 2H, Ar), 7.26–7.30 (m, 2H, Ar) ppm; 13C NMR (75 MHz, CDCl3):
δ = 168.1, 136.3, 130.4, 128.3, 128.2, 66.4 (CH2), 65.3 (CH2), 51.9 (CH3) ppm; MS (EI) m/z
(%) = 315 [M + 1]+ (6%), 314 [M]+ (7%), 313 [M − 1]+ (12%), 283 (17%), 255 (12%), 241
(51%), 209 (100%), 178 (28%), 135 (100%), 105 (26%), 45 (43%); Anal. Calcd. for C26H22O7S
(478.51): C, 65.26; H, 4.63. Found: C, 65.24; H, 4.62.

Journal of Sulfur Chemistry 331
4.2. General procedure for the synthesis of aza crowns under reflux conditions
(conventional heating)
To methanol (100 ml) were added the diester (2 mmol) and the appropriate diamine (2 mmol)
at room temperature. After stirring for 20 min at room temperature, the resulting mixture was
refluxed for 24 h. After completion of the reaction (monitored by TLC), the reaction mixture was
allowed to cool to room temperature, poured onto distilled water and the resulting mixture was
extracted with chloroform (3 × 50 ml). The combined chloroform layers were dried (Na2SO4) and
evaporated to afford a precipitate that was purified by silica gel column chromatography using
appropriate solvent mixtures as eluent.
4.3. General procedure for the synthesis of aza crowns under MW irradiation
To ethyleneglycol (20 ml) in a MW cell were added the diester (2 mmol) and the appropriate
diamine (2 mmol) at room temperature. After stirring for 10 min at room temperature, the cell was
placed in MW. Irradiation was performed for 9 min (3 × 3 min) at 100 ◦C (300W) and the rest time
was 20 min. (2 × 10 min.).After completion of the reaction (monitored by TLC), the reaction mix-
ture was allowed to cool to room temperature, poured into distilled water and the resulting mixture
was extracted with chloroform (3 × 50 ml), the combined chloroform layers were dried (Na2SO4)
and evaporated to afford a precipitate, which was purified by silica gel column chromatography
using appropriate solvent mixtures as eluent.
4.4. Synthesis of 4,7,10-triaza-15,16-benzo-3,11-dioxo-1,13-dithia-cycloheptadecane (3)
Based on the general procedures, 3 was synthesized from the reaction of diester (2) and diethylen-
etriamine under conventional heating (refluxing methanol) and under MW irradiation, and then
purified by column chromatography using chloroform/methanol (3:1) as eluent (Rf = 0.3). Under
these two conditions, conventional heating and MW irradiation, 3 was prepared in 19% and 88%
yields, respectively (Table 1), with a melting point of 139–140 ◦C; IR (KBr): 3459 (NH amide),
=
3102, 3016, 2971, 2957, 1694 (C O), 1681, 1527, 1474, 1466, 1352, 1289, 1246, 1183, 1046,
1
805 cm−1; H NMR (500 MHz, DMSO-d6): δ = 2.60–2.64 (m, 4H, CH2), 3.08–3.11 (m, 4H,
CH2), 3.20 (s, 4H, CH2), 3.90 (s, 4H, CH2), 7.21–7.22 (m, 3H, Ar, NH amide), 7.28 (s, 1H,
Ar), 7.34–7.35 (m, 1H, Ar), 7.98 (s, 1H, Ar) ppm; 13C NMR (125 MHz, DMSO-d6): δ = 169.8,
137.0, 131.3, 130.7, 128.2, 67.9 (CH2), 49.1 (CH2), 36.6 (CH2), 34.2 (CH2), 33.8 (CH2) ppm;
MS (EI) m/z (%) = 355 [M]+ (5%), 354 (41%), 336 (7%), 295 (48%), 194 (73%), 167 (76%),
135 (100%), 104 (49%), 56 (31%); Anal. Calcd. for C16H23N3O2S2 (353.5): C, 54.36; H, 6.56;
N, 11.89. Found: C, 54.34; H, 6.55; N, 11.91.
4.5. Synthesis of 4,7-diaza-12,13-benzo-3,8-dioxo-1,10-dithia-cyclotetradecane (4)
Based on the general procedures, 4 was synthesized from the reaction of diester (2) and ethylene-
diamine under conventional heating (refluxing methanol) and under MW irradiation, and then
purified by column chromatography using chloroform/methanol (4:1) as eluent (Rf = 0.8). Under
these two conditions, conventional heating and MW irradiation, 4 was prepared in 14% and 91%
yields, respectively(Table 1), andwithameltingpointof101–102 ◦C;IR(KBr): 3451(NHamide),
1
2922, 2536, 1708 (C O), 1418, 1285, 1124, 948, 754 cm−1; H NMR (500 MHz, DMSO-d6):
=
δ = 2.35 (s, 4H, CH2), 3.20 (s, 4H, CH2), 3.30 (d, J = 5 Hz, 1H, CH2), 3.33 (b, 1H, CH2), 3.95 (s,
4H, CH2), 7.22–7.24 (m, 1H, Ar), 7.26–7.33 (m, 2H), 7.82–7.84 (d, J = 1 Hz, 1H, Ar) ppm; 13
C
NMR (125 MHz, DMSO-d6): δ = 172.2, 169.8, 168.1, 143.8, 136.7, 136.4, 131.5, 131.4, 130.1,

332 E. Rostami et al.
129.9, 128.9, 128.6, 128.2, 60.4 (CH2), 59.7 (CH2), 39.3 (CH2), 36.67 (CH2) ppm; MS (EI) m/z
(%) = 312 [M + 2]+ (5%), 311 [M + 1]+ (19%), 310 [M]+ (6%), 195 (28%), 176 (46%), 135
(100%), 104 (15%);Anal. Calcd. for C14H18N2O2S2: (310.43): C, 54.17; H, 5.84; N, 9.02. Found:
C, 54.16; H, 5.83; N, 9.05.
4.6. Synthesis of 4,8-diaza-13,14-benzo-3,9-dioxo-1,11-dithia-cyclopentadecane (5)
Based on the general procedures, 5 was synthesized from the reaction of diester (2) and 1,3-
diaminopropane under conventional heating and under MW irradiation, and then purified by
column chromatography using dichloromethane/methanol (3:1) as eluent (Rf = 0.6). Under these
two conditions, conventional heating and MW irradiation, 5 was prepared in 16% and 86% yields,
respectively (Table 1), and with a melting point of 93–94 ◦C; IR (KBr): 3310 (NH amide), 2956,
1
2631, 1711 (C O), 1677, 1563, 1426, 1273, 1165, 1116, 956, 753 cm−1; H NMR (500 MHz,
=
DMSO-d6): δ = 1.68 (s, 2H, CH2), 2.37 (s, 2H, CH2), 2.86 (s, 2H, CH2), 3.23 (s, 4H, CH2),
3.97 (s, 4H, CH2), 7.21–7.22 (m, 1H, Ar), 7.33–7.35 (m, 1H), 7.38 (d, J = 10 Hz, 1H, Ar), 7.79
(d, J = 10 Hz, 1H, Ar) ppm; 13C NMR (125 MHz, DMSO-d6): δ = 171.5, 169.3, 142.7, 136.4,
131.6, 131.1, 130.3, 129.5, 128.9, 128.5, 67.9 (CH2), 63.4 (CH2), 38.1 (CH2), 37.9 (CH2) ppm;
MS (EI) m/z (%) = 324 [M]+ (12%), 227 (8%), 208 (26%), 194 (32%), 176 (17%), 167 (14%),
135 (81%), 119 (43%), 91 (100%), 65 (24%), 39 (29%);Anal. Calcd. for C15H20N2O2S2 (324.46):
C, 55.53; H, 6.21; N, 8.63. Found: C, 55.54; H, 6.20; N, 8.65.
4.7. Synthesis of 4,9-diaza-14,15-benzo-3,10-dioxo-1,12-dithia-cyclohexadecane(6)
Based on the general procedures, 6 was synthesized from the reaction of diester (2) and 1,4-
diaminobutane under conventional heating (refluxing methanol) and under MW irradiation, and
then purified by column chromatography using dichloromethane/methanol (4:1) as eluent (Rf =
0.7). Under these two conditions, conventional heating and MW irradiation, 6 was prepared in
13% and 83% yields, respectively (Table 1), and with a melting point of 89–90 ◦C; IR (KBr):
=
3367 (NH amide), 2946, 2618, 1714 (C O), 1657, 1596, 1527, 1427, 1391, 1289, 1163, 1136,
977, 839, 755 cm−1; 1H NMR (500 MHz, DMSO-d6): δ = 1.17 (s, 2H, CH2), 1.47 (d, J = 7.5 Hz,
2H, CH2), 2.73 (d, J = 7.5 Hz, 2H, CH2), 2.99 (d, J = 3.5 Hz, 2H, CH2), 3.26 (s, 4H, CH2), 3.95
(s, 4H, CH2), 7.20–7.23 (m, 1H, Ar), 7.27–7.29 (m, 1H), 7.35–7.38 (m, 1H, Ar), 7.89–7.91 (m,
1H, Ar) ppm; 13C NMR (125 MHz, DMSO-d6): δ = 168.2, 137.1, 131.9, 131.1, 130.6, 128.7,
128.0, 69.15 (CH2), 58.2 (CH2), 38.9 (CH2), 36.5 (CH2), 34.7 (CH2), 34.1(CH2), 22.6 (CH2),
22.1 (CH2) ppm; MS (EI) m/z (%) = 338 [M]+ (14%), 295 (21%), 236 (7%), 218 (15%), 200
(26%), 194 (73%), 168 (78%), 146 (18%), 135 (100%), 105 (52%), 91 (43%), 77 (20%), 45
(86%), 39 (47%); Anal. Calcd. for C16H22N2O2S2 (338.49): C, 56.77; H, 6.55; N, 8.28. Found:
C, 56.75; H, 6.56; N, 8.31.
4.8. Synthesis of 4,11-diaza-16,17-benzo-3,12-dioxo-1,14-dithia-cyclooctadecane(7)
Based on the general procedures, 7 was synthesized from the reaction of diester (2) and 1,6-
diaminohexane under conventional heating (refluxing methanol) and under MW irradiation, and
then purified by column chromatography using dichloromethane/methanol (4:1) as eluent (Rf =
0.7). Under these two conditions, conventional heating and MW irradiation, 7 was prepared in
9% and 74% yields, respectively (Table 1), and with a melting point of 82–83 ◦C; IR (KBr): 3411
=
(NH amide), 2986, 2927, 2635, 1721 (C O), 1683, 1576, 1427, 1406, 1293, 1277, 1182, 1123,
1053, 956, 843 cm−1; 1H NMR (500 MHz, DMSO-d6): δ = 2.39 (s, 4H, CH2), 3.25–3.30 (b, 2H,
CH2), 3.41 (s, 4H, CH2), 3.87 (dd, J = 3, 5 Hz, 4H, CH2), 3.98 (s, 4H, CH2), 4.31 (dd, J = 5.5,

Journal of Sulfur Chemistry 333
6.5 Hz, 4H, CH2), 7.25 (dd, J = 3.5, 5 Hz, 1H, Ar), 7.27–7.31 (m, 1H), 7.93–7.95 (b, 1H), 8.53
(dd, J = 3.5, 5 Hz, 1H, Ar) ppm; 13C NMR (125 MHz, DMSO-d6): δ = 168.8, 138.1, 132.1,
131.6, 131.2, 130.9, 128.7, 128.2, 68.3 (CH2), 67.7 (CH2), 67.6 (CH2), 61.2 (CH2), 58.9 (CH2),
33.0 (CH2), 32.9 (CH2), 32.1 (CH2) ppm; MS (EI) m/z (%) = 366 [M]+ (16%), 347 (26%), 302
(12%), 295 (45%), 236 (11%), 200 (27%), 168 (72%), 135 (100%), 104 (51%), 91 (25%), 69
(22%), 56 (32%); Anal. Calcd. for C18H26N2O2S2 (366.54): C, 58.98; H, 7.15; N, 7.64. Found:
C, 58.96; H, 7.14; N, 7.66.
Acknowledgement
The financial support of this work by Payame Noor University (PNU) Research Council is acknowledged.
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