A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H)-dione and Octahydroacridin-10(1H)-yl)thiourea Derivatives: Inter- And Intramolecular Aza-Michael addition

Article abstract of DOI:10.1515/hc-2020-0005

An easy and convenient technique for the one-pot synthesis of novel compounds of hexahydroacridine-1,8(2H,5H)-dione and octahydroacridin-10(1H)-yl) thiourea derivatives has been developed by the reaction of the octahydro-1H-xanthenes with hydroxylamine hydrochloride and thiosemicarbazide in ethylene glycol, which is a green solvent, under mild reaction conditions. IR, ¹H NMR, ¹³C NMR spectrometry, and X-ray diffraction analysis were used to identify the structures of these compounds.

Full text of DOI:10.1515/hc-2020-0005

Heterocycl. Commun. 2020; 26: 26–32
Research Article
Open Access
Nader Noroozi Pesyan*, Narmin Akhteh, Hana Batmani, Barış Anıl and Ertan Şahin
A Facile and Catalyst-free Synthesis of
Hexahydroacridine-1,8(2H,5Hꢀ)-dione and
Octahydroacridin-10(1Hꢀ)-yl)thiourea Derivatives:
Inter- and Intramolecular Aza-Michael addition
https://doi.org/10.1515/hc-2020-0005
Received October 16, 2019; accepted January 21, 2020.
activities [11]. One of the well-known classes of bioac-
tive compounds is acridine derivatives [12]. Among this
class, proflavine and 9-aminoacridine were previously
Abstract: An easy and convenient technique for the
used as antibacterial agents. However, many derivatives
one-pot synthesis of novel compounds of hexahydroac-
of 9-arylaminoacridines have been widely studied as
ridine-1,8(2H,5H)-dione and octahydroacridin-10(1H)-yl)
anticancer drugs [13,14]. It should be mentioned that the
thiourea derivatives has been developed by the reaction of
biological activities of the acridines is mainly because of
the octahydro-1H-xanthenes with hydroxylamine hydro-
the ability of the acridine moiety to intercalate between
chloride and thiosemicarbazide in ethylene glycol, which
base pairs of double-stranded DNA through π-π inter-
is a green solvent, under mild reaction conditions. IR,
actions. This matter causes alteration in the cellular
1H NMR, 13C NMR spectrometry, and X-ray diffraction
machinery [15]. For 9-arylaminoacridines, the forma-
analysis were used to identify the structures of these
tion of ternary drug/DNA/enzyme complexes was inves-
compounds.
tigated. Based on the results, it can be suggested that
the acridine moiety and aniline ring should be used
Keywords: Cyclohexanedione, Octahydro-1H-xanthene,
for the DNA-binding and the enzyme-binding domains,
Acridine, X-ray, 1D-Polymeric H-bond
respectively [13,16].
In this study, an easy and efficient technique has been
proposed for the one-pot synthesis of novel hexahydroac-
Introduction
ridine-1,8(2H,5H)-dione and octahydroacridin-10(1H)-yl)
thiourea derivatives by the reaction of octahydro-1H-
Acridine derivatives have a significant location in medi-
xanthenes with hydroxylamine hydrochloride and thiose-
cinal chemistry because of their extensive applications
micarbazide in ethylene glycol, which is a green solvent.
in biology. These derivatives exhibit fungicidal [1,2],
anti-cancer [3-5], anti-parasitic [6], anti-inflammatory,
and anti-microbial activities [7,8]. In addition, they are
important components of effective analgesics [9,10].
Results and Discussion
Mepacrine, azacrine, proflavine, and aminacrine, are
some other pharmaceutically active acridine deriva-
This manuscript describes the synthesis of novel
tives, which also show antimalarial and antibacterial
hexahydroacridine-1,8(2H,5H)-dione and octahydroacridin-
10(1H)-yl)thiourea derivatives from reaction of octahydro-1H-
xanthenes with hydroxylamine hydrochloride and thiose-
* Corresponding author: Nader Noroozi Pesyan, Department of
Organic Chemistry, Faculty of Chemistry, Urmia University, 57159,
Urmia, IRAN, email: n.noroozi@urmia.ac.ir, nnp403@gmail.com
Narmin Akhteh, Hana Batmani, Department of Organic Chemistry,
Faculty of Chemistry, Urmia University, 57159, Urmia, IRAN
Barış Anıl and Ertan Şahin, Department of Chemistry, Faculty of
Science, Atatürk University, 25240 Erzurum, Turkey
micarbazide. Since the usage of simply available reagents
is a meaningful target in organic synthesis and in order
to extend synthetic methods for the synthesis of hexa-
hydroacridine-1,8(2H,5H)-dione and octahydroacridin-
10(1H)-yl) thiourea, this paper now establishes
a
simple and expedient method using hydroxylamine
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Attribution alone 4.0 License.
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hydrochloride and thiosemicarbazide as
a worthy stretching frequency of 1b, 2b and 3b are shown at 1653,
-1
nitrogen source in ethylene glycol, which is a green 1699 and 1662 cm , respectively. These observations con-
solvent. In an easy reaction work-up mixture and in a firmed the expansion of the conjugation in compounds 2
short period of the reaction time, high yields of products and 3. A peak at δ 10.76 ppm is seen in 1H NMR spectrum
are achieved under mild reaction conditions with no of 2a which corresponded to a hydroxylamine proton (see
catalyst (Scheme 1).
Supplementary Data). The 13C NMR spectrum of 1a also
Firstly, the reaction of octahydro-1H-xanthenes 1 [17] displayed a peak at δ 205.17 ppm which corresponded to
with hydroxylamine hydrochloride or thiosemicarbazide a saturated ketone carbonyl group instead, this peak dis-
in different solvents and at various temperatures was appeared in the 13C NMR spectrum of 2a and shifted to up
examined. The obtained results disclose that the usage field position and showed a distinct peak at δ 194.92 ppm
of ethylene glycol at 100 °C is the optimal temperature (see Supplementary Data). This distinct peak confirmed
for the one-pot reaction of octahydro-1H-xanthenes with the presence of a plane of symmetry in 2.
hydroxylamine hydrochloride and thiosemicarbazide.
Crystal structure of 10-hydroxy-9-(4-nitro-phenyl)-
Table 1 represents the results of the reactions of several 3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione (2d) with
octahydro-1H-xanthenes with hydroxylamine hydrochlo- the atom labeling scheme is depicted in Figure 1a. Com-
ride or thiosemicarbazide.
pounds 2d crystallize in the monoclinic space groups P21/n
The reaction mechanism is shown in Scheme 2. In with the four molecules in the unit cell. 3,4,6,7,9,10-Hexa-
the course of the reaction, dehydration of 1a, in the pre- hydro-2H,5H-acridine-1,8-dione ring system is substituted
sence of hydroxylamine, obtained compound A. Then at the central methine C7 atom with a 4-nitro-phenyl. In
aza-Michael addition [18-20] of hydroxylamine to the addition, it carries a hydroxy substituent on the acridine
β position of the α,β-unsaturated ketone generated an N atom. C-C (cyclohexene) distances are in the range of
intermediate B. The ethereal ring opening of intermediate typical single bond range [1.461(3)–1.521(3) Å]. The C7
B led to the generation of intermediate C. Intramolecular carbon atom is not a stereocenter since the structure is
aza-Michael addition of hydroxylamine to the β-position symmetric. For the thirteen C atoms and one N atom of
of the other α,β-unsaturated ketone in the intermediate the acridine unit, the acridinedione ring system deviates
C moiety, resulted in conversion into an intermediate D. meaningfully from planarity with an r.m.s. deviation of
This intermediate gave 2a with the loss of a water mole- 0.614 Å. Such a plane is not quite orthogonal to the benzene
cule (Scheme 2).
ring plane [dihedral angle = 89.3°], a stable conformation
…
The ketone carbonyl group in 1b has a stretching fre- is obtained by a strong intermolecular O5−H O2 hydrogen
-1
quency at 1723 cm . This peak is lost in the compounds bond between the two adjacent molecules (Figure 1b). It
2b and 3b. Instead, the peak of α,β-unsaturated carbonyl is worth mentioning that in the reverse direction, both
Scheme 1
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N.N. Pesyan et al.: A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5Hꢀ)-dione
Table 1ꢂOne-pot synthesis of hexahydroacridine-1,8(2H,5H)-dione 2 and octahydroacridin-10(1H)-yl)thiourea derivatives 3.
Entry
Product
Time (h)
Yield (%)a
Mp (°C)
(a)
(b)
1
2
73
238–239
2
3
3
3
76
69
225
–
(c)
4
5
0.5
62
68
245
210
(d)
(e)
6
(Continued)
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N.N. Pesyan et al.: A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5Hꢀ)-dioneꢁ
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Table 1ꢂContinued.
Entry
Product
Time (h)
Yield (%)a
Mp (°C)
6
7
3
88
257
ꢁꢁ(a)
ꢁꢁ(b)
2
2
54
45
231–234
229–231
8
ꢁꢁ(f)
aIsolated yield.
(a)
(b)
ꢀ
Figure 1ꢀ(a) Molecular structure of the compound 2d. Thermal ellipsoids are depicted at the 40% probability, (b) 1D-polymeric H-bonding
geometry.
outer cyclohexenone rings adopt flattened chair configu-
On a four-circle Rigaku R-AXIS RAPID-S diffracto-
rations with the C11 and C16 atoms each about 0.320(4) Å meter which was equipped with a two-dimensional area
from the best-fit planes through the remaining five C IP detector, a single-crystal of the compound 2d was
atoms. On the other hand, from the best-fit plane through employed to collect data for the crystal structure determi-
the other four C atoms, the central C13/N2/C7-C8/C14/C19 nation. In addition, Graphite-monochromated Mo-Kα radi-
ring could be perfectly described as a flattened boat with ation (l = 0.71073 Å) and oscillation scans technique with
N2 and C7, 0.048(4) and 0.109(4) Å, respectively. Note that Dw = 5° for one image were also utilized for collecting
the bond angles and lengths in the molecule of 2d agree some data. Using the least-squares (LS) methods on the
well with ones found in closely related molecules [21,22].
basis of reflections with F2 > 2s(F2), the lattice parameters
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N.N. Pesyan et al.: A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5Hꢀ)-dione
Scheme 2
were estimated. CrystalClear (Rigaku/MSC Inc., 2005) Conclusion
software was applied for integration of the intensities,
correction for Lorentz and polarization effects, and cell In closing, an easy and efficient technique has been pro-
refinement [23]. Direct methods using SHELXS-97 were posed for the one-pot synthesis of novel compounds of
used to solve the structures [24], which permitted for the hexahydroacridine-1,8(2H,5H)-dione and octahydroac-
location of the heaviest atoms. In this case, the remaining ridin-10(1H)-yl) thiourea derivatives by the reaction of
non-hydrogen atoms were located from different Fourier octahydro-1H-xanthenes with hydroxylamine hydrochlo-
maps which were calculated using some successive full- ride and thiosemicarbazide in ethylene glycol, which is a
matrix least squares refinement cycles on F2 using SHELXL- green solvent. The main advantages of this protocol are
97 [24]. Anisotropic displacement parameters were utilized as follows: (i) it is a simple procedure under mild reaction
to refine all non-hydrogen atoms. Appropriate HFIX inst- conditions; (ii) high yields of the products are obtained;
ructions in SHELXL were employed to attach hydrogens (iii) reaction times are short; (iv) it uses hydroxylamine
to carbons located at their geometric positions. It should hydrochloride and thiosemicarbazide as commercially
be reported that no peaks of chemical significance were available, inexpensive, and easy-to-handle reagents;
observed in the final difference Fourier maps. Crystal data especially in comparison with a large number of nitrogen
for 2d: C19H18N2O5, crystal system, space group: mono- sources.
clinic, P21/n; (no:14); unit cell dimensions: a = 9.213(2),
b = 16.571(4), c = 12.034(2) Å, α = 90, β = 112.059(6), γ = 90°;
volume: 1721.2(6) Å3; Z = 4; calculated density: 1.367 g/cm3;
-1
absorption coefficient: 0.10 mm ; F(000)= 744; θ-range for Experimental
data collection 2.1–25.5°; refinement method: full matrix
least-square on F2; data/parameters: 3171/239; goodness- Materials and apparatus
of-fit on Fꢀ2: 1.168; final R-indices [I > 2s(I)]: R1 = 0.076,
wR2 = 0.182; largest diff. peak and hole: 0.366 and -0.311 The 1,3-cyclohexanedione, aldehyde derivatives, triethyl-
-3
e Å . The Cambridge Crystallographic Data Center as sup- amine, hydroxylamine hydrochloride, thiosemicarbazide,
plementary publication no. CCDC-1841461 was used to and solvents were purchased from Merck and Aldrich.
deposit crystallographic data for the structure 2d. Copies They were used without any further purification. Cyano-
of these utilized data are available by application to CCDC, gen bromide was also synthesized using reported litera-
12 Union Road, Cambridge CB2 1EZ, UK; FAX: (+44) 1223 ture [25]. Thin-layer chromatography (TLC), carried out
336033, or online via www.ccdc.cam.ac.uk/data_request/ on silica gel plates (SILG/UV 254, Merk) using UV light as
cif, or by sending emails to data_request@ccdc.cam.ac.uk the visualizing agent, was used to monitor the reactions.
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N.N. Pesyan et al.: A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5Hꢀ)-dioneꢁ
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Electrothermal 9100 apparatus were employed to measure 5.06 (s, 1H, OH), 2.85-2.79 (m, 2H), 2.64-2.49 (m, 2H), 2.26-
the melting points. On a Nexus 670 model Bruker FT-IR 2.08 (m, 4H), 2.01-1.99 (m, 1H), 2.01-1.78 (m, 4H). 13C NMR
spectrophotometer, KBr pellets were used to record IR (75 MHz in DMSO-d6): δ (ppm) = 194.92, 154.62, 146.44,
spectra. A Bruker Advance 300 MHz (300 MHz for 1H) was 129.44, 129.38, 128.54, 127.48, 127.41, 126.44, 125.15, 110.89,
1
also used to record H NMR and 13C NMR spectra. Chemi- 110.83, 36.67, 30.52, 30.48, 26.11, 25.23, 24.00, 21.21,
cal shifts were recorded in ppm downfield from tetrame- 20.74, 19.56.
thylsilane and coupling constants J are reported in Hz.
10-Hydroxy-9-(2-nitrophenyl)-3,4,6,7,9,10-
Abbreviations used in 1H NMR are s (singlet), d (doublet), hexahydroacridine-1,8(2H,5H)-dione 2b (Table 1, entry 2):
t (triplet), q (quartet) and m (multiplet).
Brown solid, mp: 225oC.
-1
FT-IR (KBr): υ (cm ) = 3405, 2946, 2884, 1698, 1527,
1447, 1345, 1240, 1168, 1129, 1060, 940, 866, 785, 757, 700,
1
637,543. H NMR (300 MHz in DMSO-d6) δ (ppm) = 10.58
General reaction procedure
(s, 1H, OH), 8.17-7.77 (m, 3H), 7.74-6.92 (m, 10H), 4.8 (s, 1H,
OH), 4.01-3.90 (m, 2H), 3.10-2.86 (m, 3H), 2.37-2.74 (m, 17H),
1.73-1.02 (m, 12H). 13C NMR (75 MHz in DMSO-d6): δ (ppm) =
197.80, 173.06, 163.64, 160.61, 159.95, 158.71, 158.856, 154.27,
152.09, 150.107, 149.78, 149.17, 148.708, 148.12, 147.56, 146.71,
137.70, 136,63, 135.288, 133.646, 133.236, 132.17, 130.34,
129.80, 128.88, 128. 412, 127.89, 127.433, 126.88, 126.68,
126.59, 126.369, 126.59, 126.37, 125.87, 124.79, 124.60, 124.43,
123.39, 122.82, 122.25, 108.16, 107.823, 107, 67.86, 66.11, 65,
64.36, 63.84, 63.11, 61.21, 59.42, 57.61.
Synthesis of the 4a-hydroxy-9-aryl-3,4,4a,5,6,7,9,9a-
octahydro-1H-xanthene-1,8(2H)-dione 1 Triethylamine
(2.6 mmol) was added to a stirring mixture of 1,3-
cyclohexanedione (4.0 mmol) and aldehyde deriva-
tive (2.0 mmol) in methanol (10.0 mL) and stirred for 20
min. Then, the reaction mixture was added dropwise
to cyanogen bromide (2.0 mmol) in methanol (4.0 mL)
and the mixture was stirred in an ice bath. Monito-
ring of the reaction with TLC analysis (n-hexane/EtOAc
(10/8) showed the reaction was completed within 24 h.
After the reaction had reached completion, the solvent
was removed under reduced pressure and afforded the
octahydro-1H-xanthene products in good to excellent yields.
Reaction products were characterized by IR, 1H NMR and
13C NMR spectrometry.
10-Hydroxy-9-(4-nitrophenyl)-3,4,6,7,9,10-hexa-
hydroacridine 1,8(2H,5H)-dione 2d (Table 1, entry 4):
Yellow solid, mp: 245oC.
-1
FT-IR (KBr): υ (cm ) = 3432.9, 2930.9, 2702.9, 1643.2,
1514, 1351.6, 1231.6, 1175.4, 1126.9, 955.8, 909.5, 824.4, 699.6,
595.7, 537.6. 1H NMR (300 MHz in DMSO-d6) δ (ppm) = 10.84
(s, 1H, OH), 8.07 (d, 2H, J =8.1Hz), 7.48-7.36 (m, 3H), 5.15
(s, 1H, OH), 2.86-2.80 (m, 2H), 2.65-2.49 (m, 8H), 2.24-1.82
(m, 4H). 13C NMR (75 MHz in DMSO-d6): δ (ppm) = 196.73,
194.89, 165.80, 155.18, 153.93, 131.01, 129.94, 127.79, 124.82,
124.66, 122.73, 122.53, 114.84, 109.85, 36.50, 35.28, 31.55,
Synthesis of the compounds 2
A mixture of octahydro-1H-xanthene 1 (0.31 mmol) and 26.99, 26.07, 25.33, 24.17.
hydroxylamine hydrochloride (0.31 mmol, 0.02 g) in
9-(4-Fluorophenyl)-10-hydroxy-3,4,6,7,9,10-hexa-
ethylene glycol (8 mL) was stirred at 100°C, for an appro- hydroacridine-1,8(2H,5H)-dione 2e (Table 1, entry 5):
priate time. The reaction progress was monitored by TLC White solid, mp: 210oC.
-1
analysis (n-hexane/EtOAc (6/3). After the reaction had
FT-IR (KBr): υ (cm ) = 3414, 2943, 2885, 2705, 1643,
reached completion, the reaction mixture was cooled 1602, 1510, 1364, 1308, 1232, 1177, 1133, 956, 907, 839, 688,
1
to room temperature and then, it was extracted with 605, 545. H NMR (300 MHz in DMSO-d6) δ (ppm) = 10.77
H2O and CH2Cl2. Under reduced pressure, the organic (s, 1H, OH), 7.11-6.99 (m, 6H), 5.04 (s, 1H, OH), 2.83-2.78 (m,
layer was evaporated and then, it afforded the xanthene 2H), 2.62-2.48 (m, 2H), 2.22-1.94 (m, 6H), 1.94-1.77 (m, 7H).
oxime 2 products in good to excellent yields. Reaction 13C NMR (75 MHz in DMSO-d6): δ (ppm) = 194.92, 154.66,
products were characterized by IR, H NMR and 13C NMR 142.61, 131.32, 130.28, 128.13, 116.28, 116.05, 115.83, 114.06,
1
spectrometry.
10-Hydroxy-9-phenyl-3,4,6,7,9,10-hexahydro-
110.78, 36.61, 31.61, 30.04, 25.99, 24.64, 23.99, 31.30.
4.2.3 Synthesis of the 1-(1,8-dioxo-9-aryl-
acridine-1,8(2H,5H)-dione 2a [18] (Table 1, entry 1): 2,3,4,5,6,7,8,9-octahydroacridin-10(1H)-yl)thiourea
Green solid, mp: 238–239 oC.
derivatives 3 A mixture of octahydro-1H-xanthene 1
-1
FT-IR (KBr): υ (cm ) = 3402, 2943, 2880, 1618, 1362, (0.25 mmol) and thiosemicarbazide (0.25 mmol, 0.02 g)
1
1302, 1234, 1177, 1127, 943, 903, 770. H NMR (300 MHz in ethylene glycol (8 mL) was stirred at 100°C, for a sui-
in CDCl3): δ (ppm) = 10.75 (s, 1H, OH), 7.20-7.04 (m, 5H), table period of time. TLC analysis (n-hexane/EtOAc (9/3)
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N.N. Pesyan et al.: A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5Hꢀ)-dione
[9] Taraporewala IB, Kauffman JM. Synthesis and structure–activity
relationships of anti‐inflammatory 9, 10‐dihydro‐9‐
oxo‐2‐acridine‐alkanoic acids and 4‐(2‐carboxyphenyl)
aminobenzenealkanoic acids. J Pharm Sci. 1990;79:173.
[10] Gaidukevich AN, Kazakov GP, Kravchenko AA, Porokhnyak LA,
Dinchuk VV. Synthesis and biological activity of acridinyl-9-
thioacetic acids and their derivatives. Khim Farm Zh. 1987;21:1067.
[11] Denny WA, Baguley BC, Cain BF, Waring MJ (Neidle S, Waring
MJ, editors). Antitumor acridines in molecular aspects of
anticancer drug action. London: Macmillan; 1983. pp. 1–34.
[12] Denny WA. Acridine derivatives as chemotherapeutic agents.
Curr Med Chem. 2002;9:1655.
[13] Bacherikov VA, Chou TC, Dong HJ, Zhang X, Chen CH, Lin Y.
W.; Tsai, T. J.; Lee, R. Z.; Liu, L. F.; Su, T. L. Potent antitumor
9-anilinoacridines bearing an alkylating N-mustard residue on
the anilino ring: synthesis and biological activity. Bioorg Med
Chem. 2003;13:3993.
was used to monitor the reaction progress. After the
reaction had reached completion, the reaction mixture
was cooled to the room temperature and then it was fil-
tered. The products were washed with deionized water
and dried in air. This afforded the thiosemicarbazone
3 products in good to perfect yields. Reaction products
1
were characterized by IR. But we could not take H NMR
and 13C NMR spectrometry from thiosemicarbazone
3 products, because these compounds were insoluble in
DMSO solvent.
1-(1,8-Dioxo-9-phenyl-2,3,4,5,6,7,8,9-octahydroac-
ridin-10(1H)-yl)thiourea 3a (Table 1, entry 6): Yellow
-1
solid, mp: 257 oC. FT-IR (KBr): υ (cm ) = 3684, 3441, 3074,
2944, 2886, 1660, 1362, 1179, 1131, 958, 704, 622, 543.
1-(9-(2-Nitrophenyl)-1,8-dioxo-2,3,4,5,6,7,8,9-octahy-
droacridin-10(1H)-yl)thiourea 3b (Table 1, entry 7): Yellow
[14] Kumar R, Singh M, Prasad DN, Silicari O, Sharma S. Synthesis
and chemical characterization of 9-anilinoacridines. Chem Sci
Trans. 2013;2:246.
-1
solid, mp: 231–234oC. FT-IR (KBr): υ (cm ) = 3428, 3256, 3146,
[15] Joseph J, Kuruvilla E, Achuthan AT, Ramaiah D, Schuster
GB. Tuning of intercalation and electron-transfer processes
between DNA and acridinium derivatives through steric effects.
Bioconjug Chem. 2004;15:1230.
[16] Gao H, Denny WA, Garg R, Hansch C. Quantitative structure–
activity relationships (QSAR) for 9-anilinoacridines: a
comparative analysis. Chem Biol Interact. 1998;116:157.
[17] Fun HK, Ooi CW, Reddy BP, Vijayakumar V, Sarveswari
S. 10a-Hydroxy-9-(4-methoxyphenyl)-3, 4, 5, 6, 7, 8a, 9,
10a-octahydro-1H-xanthene-1, 8 (2H)-dione. Acta Crystallogr
Sect E Struct Rep Online. 2012;68:2367.
2984, 2811, 1590, 1530, 1461, 1370, 1284, 1094, 820, 468.
1-(9-(2,4-Dichlorophenyl)-1,8-dioxo-2,3,4,5,6,7,8,9-
octahydroacridin-10(1H)-yl)thiourea 3f (Table 1,
o
entry 8): Brown solid, mp: 229-231 C. FT-IR (KBr): υ
-1
(cm ) = 3739, 3452, 3078, 2962, 2897, 1662, 1622, 1520, 1361,
1202, 1178, 1130, 1013, 962, 786, 616, 539.
Acknowledgements: We gratefully acknowledge financial
support from the Research Council of Urmia University.
[18] Pyrko AN. Synthesis and transformations of new
1,2,3,4,5,6,7,8,9,10- decahydroacridine-1,8-dione derivatives.
Russ J Org Chem. 2008;44:1215.
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