Solvent-free one pot synthesis of indenoquinolinones catalyzed by iron(III) trifl ate

Article abstract of DOI:10.1515/HC.2011.028

A green three-component one pot condensation synthesis of 16 indenoquinolinone from aromatic aldehydes, 1-aminonaphthalene or 1-aminoanthracene and 1,3-indanedione catalyzed by Fe(OTf)₃ is described. The isolated yields ranged from 80 % to 92 %

Full text of DOI:10.1515/HC.2011.028

Heterocycl. Commun., Vol. 17(3-4), pp. 121–124, 2011 • Copyright © by Walter de Gruyter • Berlin • Boston. DOI 10.1515/HC.2011.028
Solvent-free one pot synthesis of indenoquinolinones
catalyzed by iron(III) triflate
Saman Damavandi1,* and Reza Sandaroos2
(Tu et al., 2006b; Wang et al., 2008). The approach involves
the reaction of either tetronic acid or 1,3-indanedione with
1Department of Chemistry, Sarvestan Branch, Islamic
various aldehydes and substituted anilines in water under
Azad University, Sarvestan, Iran
microwave irradiation conditions. Furthermore, a one pot
2Department of Chemistry, Faculty of Science, Birjand
synthesis of indenoquinoline derivatives by condensing
University, Birjand, Iran
1-aminonaphthalene, aldehydes and 1,3-indandione has been
reported (Heravi et al., 2010).
In contemporary organic synthesis, Lewis acid catalyzed
reactions have gained increasing interest because of the
unique reactivity and selectivity that can be achieved under
mild conditions (Santelli and Pons, 1995). During the past
few years, the outstanding potential of a variety of metal tri-
flates (trifluoromethylsulfonates) has been discovered, thus
triggering much research endeavor. The triflate anion is both
weakly nucleophilic and coordinating, rendering the metal
counter ion more cationic and thus a stronger Lewis acid.
In continuation of our interest in MCRs (Damavandi, 2011;
Eshghi et al., 2011), herein, the metal triflates catalyzed one
pot reaction of 1-aminonaphthalene or 1-aminoanthracene,
aromatic aldehydes and 1,3-indanedione providing a series
of indeno[1,2-b]quinolineone derivatives is described. To the
best of our knowledge, this is the first report on the use of
Fe(OTf)3 as a catalyst for the synthesis of such compounds.
*Corresponding author
e-mail: saman_damavandi@yahoo.com
Abstract
A green three-component one pot condensation synthesis of
16 indenoquinolinone from aromatic aldehydes, 1-aminon-
aphthalene or 1-aminoanthracene and 1,3-indanedione cata-
lyzed by Fe(OTf)3 is described. The isolated yields ranged
from 80% to 92%.
Keywords: indenoquinolinone; iron triflate; one pot
synthesis.
Introduction
Heterocycles are used as scaffolds for creating pharmaco-
phores to yield potent and selective drugs (Hermakens et
al., 1997). This is especially true for six-membered ring het-
erocyclic compounds, which are core components of a large
number of substances that possess a wide range of interesting
biological activities (Avendano and Menendez, 2008). With
an emphasis on the search for atom efficient transformations
of readily available starting materials into complex organic
molecules (Trost, 1995), reactions that provide maximum
diversity are particularly desirable. Here, expeditious dom-
ino (Padwa and Bur, 2007) and multicomponent (Zhu and
Bienaime, 2005) reactions (MCRs) have emerged as power-
ful strategies.
In view of the importance of benzoquinolines and their
derivatives in various fields of chemistry, biology and pharma-
cology, significant efforts have been devoted to their synthe-
sis. Quinoline derivatives are reported to possess interesting
pharmacological activities such as anti-plasmodial, anti-bac-
terial and anti-proliferative activities (Tu et al., 2006a; Wang
et al., 2007). Therefore, various methods such as the Skraup,
Doebner–von Miller, Friedläänder and Combes procedures
have been developed for the synthesis of quinoline deriva-
tives (Jiang and Si, 2002; Theoclitou and Robinson, 2002).
In recent years, a multicomponent approach for the syn-
thesis of indenoquinolinone derivatives has been reported
Results and discussion
First, the mixture of 4-nitrobenzaldehyde, 1-aminonaphtha-
lene and 1,3-indandione was chosen as a model reaction to
determine whether 5 mol% Fe(OTf)3 was an efficient cata-
lyst. The reaction mixture was stirred at 90°C for 4h and
the corresponding indenoquinolinone (3 in Scheme 1) was
obtained in 80% yield. No target product was observed
when the mixture was stirred under similar conditions in
the absence of Fe(OTf)3, even after heating for 6 h, thus
highlighting the role of Fe(OTf)3 as a catalyst. Next the
amount of the Fe(OTf)3was changed from 5 to 20 mol%.
The results showed that the reaction yield was improved
when the amount of Fe(OTf)3 increased from 5 to 10 mol%.
However, the yield was minimally affected when the amount
of Fe(OTf)3 was further increased from 10 to 20 mol%
(92%). Therefore, 10 mol% of Fe(OTf)3 was considered to
be suitable.
Several metal triflates were investigated in an attempt to
further optimize the reaction. The ferric catalyst Fe(OTf)3
showed the most effective catalytic effect, whereas Zn(OTf)2,
Cu(OTf)2 and triflic acid (HOTf) showed relatively lower
catalytic efficiency. The recyclability of Fe(OTf)3 was also
investigated. The catalyst could be reused without any loss
of activity.
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122 S. Damavandi and R. Sandaroos
Ar
O
NH2
O
Fe(OTf)3, 10 mol%
Solvent-free, 90°C
ArCHO
N
H
O
1-12
Ar=C6H5 - (1); 4-CH3OC6H4 - (2); 4-O2NC6H4 - (3); 4-FC6H4 - (4); 4-BrC6H4 - (5); 1-naphthyl - (6);
4-Me2NC6H4 - (7); 4-CH3C6H4 - (8); 4-ClC6H4 - (9); 3-O2NC6H4 - (10), 2-ClC6H4 - (11);
2-furanyl - (12)
Ar
O
NH2
O
Fe(OTf)3, 10 mol%
Solvent-free, 90°C
ArCHO
N
H
O
13-16
Ar=C6H5 - (13); 4-O2NC6H4 - (14); 2-furanyl - (15); 4-CH3OC6H4 - (16)
Scheme 1 Synthesis of indeno[1,2-b]quinolinone derivatives 1–16.
The generality of this process was demonstrated by
the wide range of substituted aromatic aldehydes used to
synthesize indenoquinolinone derivatives 1– 16 (Scheme 1).
Various aromatic aldehydes were allowed to react with
1-aminonaphthalene and 1,3-indanedione and all these
reactions proceeded smoothly to give the corresponding
products 1– 12 in good to excellent yields (Scheme 1).
Encouraged by these results the attention was turned to
1-aminoanthracene, the reaction of which gave the corre-
spondingindeno[1,2-b]quinoline-7-ones13– 16ingoodyields
(Scheme 1).
reaction between 1,3-indanedione and 4-nitrobenzaldehyde
was isolated and characterized. Its subsequent reaction with
1-aminoanthtracene yielded compound 14.
Conclusion
Asimple three-component reaction yielding indenoquinolinone
derivatives in a one pot procedure using iron(III) triflate as an
efficient and recyclable catalyst has been developed.
In order to gain an insight into the reaction mechanism,
4-nitrobenzyldehyde was allowed to react with 1-amino-
anthracene and the expected Schiff base A was isolated
and characterized. A subsequent treatment of compound A
with 1,3-indanedione furnished product 14 that was identi-
cal with that obtained in the one pot reaction. In a simi-
lar way, the intermediate product B (Scheme 2) from the
Experimental
General
Chemicals were either prepared in our laboratories or purchased
from Merck, Fluka and Aldrich Chemical Companies. All yields
NO2
O
O
O
H
N
HC
H2N
+
O
N
Fe(OTf)3 (10 mol%)
H
NO2
NO2
NO2
Isolated intermediate
A
NH2
O
H
O
O
O
O
CH
Ar
+
Fe(OTf)3 (10 mol%)
N
H
O
NO2
Isolated intermediate
B
Scheme 2 Synthesis of compound 14 from intermediates A and B.
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Synthesis of indenoquinolinones 123
refer to isolated products. IR spectra were recorded in KBr disks on a
Shimadzu-IR 470 spectrophotometer. 1H NMR spectra was recorded
on a Bruker 100-MHz spectrometer in DMSO-d6 with TMS as in-
ternal standard. Flash column chromatography was performed using
300- and 400-mesh silica gel and analytical thin layer chromatography
was performed on pre-coated silica gel plates (60F-254). Mass spec-
tra were recorded with a Shimadzu QP 1100 EX mass spectrometer
operating at an ionization potential of 70 eV. Elemental analyses were
performed on Thermo Finnigan EA1112 elemental analyzer.
9.95 (1H, s, NH), 7.85–7.70 (4H, m, ArH), 7.70–7.60 (4H, m, ArH),
7.55–7.05 (9H, m, ArH), 5.30 (1H, s, CH). EIMS: m/z 409 (M+).
Analysis: calculated for C30H19NO: C, 88.00; H, 4.68; N, 3.42.
Found: C, 88.15; H, 4.71; N, 3.46.
7-[4-(Dimethylamino)phenyl]-8,13-dihydro-7H-benzo[h]
indeno[1,2-b]quinolin-8-one (7): Isolated yield 84%; m.p.
323–325°C; 1H NMR: δ 10.55 (1H, s, NH), 7.80–7.55 (3H, m, ArH),
7.50–7 (7H, m, ArH), 6.95 (2H, d, J=5.2 Hz, ArH), 6.65 (2H, d,
J=5.5 Hz, ArH), 5.25 (1H, s, CH), 2.90 (6H, s, NMe2); EIMS: m/z
402 (M+). Analysis: calculated for C28H22N2O: C, 83.56; H, 5.51; N,
6.96. Found: C, 83.48; H, 5.45; N, 6.91.
General procedure for preparation of
indeno[1,2-b]quinoline-7-ones (1–16)
A mixture of aryl aldehyde (1 mmol), 1,3-indanedione (1 mmol),
amine (1 mmol), Fe(OTf)3 (10 mol%) was added to a round bot-
tomed flask. The mixture was heated at 90°C between 3–5 h as indi-
cated by TLC analysis. Upon completion of the reaction, the mixture
was extracted with AcOEt (3×10 ml) and washed with aq. NaHCO3
solution (2×10 ml) and brine (2×5 ml). Then the organic phase was
dried over MgSO4 and concentrated under reduced pressure. The
crude product was chromatographed on silica gel eluting with petro-
leum ether–AcOEt (5:1).
7-(4-Methylphenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]
quinolin-8-one (8): Isolated yield 90%; m.p. 315–317°C; 1H
NMR: δ 10.70 (1H, s, NH), 7.75–7.65 (14H, m, ArH), 5.55 (1H, s,
CH), 2.20 (3H, s, Me). EIMS: m/z 373 (M+). Analysis: calculated
for C27H19NO: C, 86.84; H, 5.13; N, 3.75. Found: C, 86.77; H, 5.19;
N, 3.71.
7-(4-Chlorophenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]
quinolin-8-one (9): Isolated yield 90%; m.p. 316–318°C; 1H
NMR: δ 9.85 (1H, s, NH), 7.75–7.45 (8H, m, ArH), 7.40 (2H, m,
ArH), 7.25–7.0 (4H, m, ArH), 4.95 (1H, s, CH); EIMS: m/z 393
(M+). Analysis: calculated for C26H16ClNO: C, 79.29; H, 4.09; N,
3.56. Found: C, 79.21; H, 4.03; N, 3.51.
7-Phenyl-8,13-dihydro-7H-benzo[h]indeno[1,2-b]quinolin-8-
1
one (1): Isolated yield 90%; m.p. 309–310°C; H NMR: δ 9.85
(1H, s, NH), 7.85 (2H, d, J=3.5 Hz, ArH), 7.75 (2H, d, J=3.7 Hz,
ArH), 7.65–7.45 (4H, m, ArH), 7.45–7.10 (7H, m, ArH), 5.10 (1H,
s, CH); EIMS: m/z 359 (M+). Analysis: calculated for C26H17NO: C,
86.88; H, 4.77; N, 3.90. Found: C, 86.72; H, 4.69; N, 3.87.
7-(3-Nitrophenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]quin-
1
olin-8-one (10): Isolated yield 90%; m.p. 334–355°C; H NMR:
δ 10.50 (1H, s, NH), 8.05 (2H, m, ArH), 7.75–7.65 (2H, m, ArH),
7.55–7.07 (10H, m, ArH), 5.35 (1H, s, CH); EIMS: m/z 404 (M+).
Analysis: calculated for C26H16N2O3: C, 77.22; H, 3.99; N, 6.93.
Found: C, 77.18; H, 4.05; N, 6.97.
7-(4-Methoxyphenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-
b]quinolin-8-one (2): Isolated yield 90%; m.p. 313–314°C; 1H
NMR: δ 10.10 (1H, s, NH), 7.80 (1H, d, J=7.3 Hz, ArH), 7.65–7.45
(4H, m, ArH), 7.55–7.10 (7H, m, ArH), 6.93 (2H, d, J=4.2 Hz, ArH),
5.25 (1H, s, CH), 3.65 (3H, S, OMe); EIMS: m/z 389 (M+). Analysis:
calculated for C26H19NO2: C, 83.27; H, 4.92; N, 3.60. Found: C,
83.12; H, 4.89; N, 3.55.
7-(2-Chlorophenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]
quinolin-8-one (11): Isolated yield 88%; m.p. 335–337°C; 1H
NMR: δ 9.85 (1H, s, NH), 7.75–7.45 (8H, m, ArH), 7.40 (2H, m,
ArH), 7.25–7.0 (4H, m, ArH), 4.95 (1H, s, CH); EIMS: m/z 393
(M+). Analysis: calculated for C26H16ClNO: C, 79.29; H, 4.09; N,
3.56. Found: C, 79.21; H, 4.03; N, 3.51.
7-(4-Nitrophenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]qui-
1
nolin-8-one (3): Isolated yield 92%; m.p. 348–350°C; H NMR:
δ 11.22 (1H, s, NH), 7.92 (1H, d, J=9 Hz, ArH), 7.78–7.45 (6H, m,
ArH), 7.36–7.10 (7H, m, ArH), 5.40 (1H, s, CH); EIMS: m/z 404
(M+). Analysis: calculated for C26H16N2O3: C, 77.22; H, 3.99; N,
6.93. Found: C, 77.12; H, 3.92; N, 6.89.
7-(2-Furyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]quinolin-8-
one (12): Isolated yield 85%; m.p. 293–295°C; H NMR: δ 9.90
(1H, s, NH), 7.85–7.75 (2H, m, ArH), 7.73–7.40 (5H, m, ArH), 7.40–
7.0 (5H, m, ArH), 6.25 (1H, t, ArH), 4.95 (1H, s, CH); EIMS: m/z
349 (M+). Analysis: calculated for C24H15NO2: C, 82.50; H, 4.33; N,
4.01. Found: C, 82.33; H, 4.30; N, 3.98.
1
7-(4-Fluorophenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]qui-
nolin-8-one (4): Isolated yield 92%; m.p. 336–338°C; 1H NMR: δ
9.80 (1H, s, NH), 7.90–7.67 (4H, m, ArH), 7.55–7.40 (4H, m, ArH),
7.35–7.10 (7H, m, ArH), 5.15 (1H, s, CH). EIMS: m/z 377 (M+).
Analysis: calculated for C26H16FNO: C, 82.74; H, 4.27; N, 3.71.
Found: C, 82.48; H, 4.19; N, 3.74.
8-Phenyl-9,14-dihydro-8H-indeno[1,2-b]naphtho[2,3-h]quino-
1
lin-9-one (13): Isolated yield 80%; m.p. 336–338oC; H NMR: δ
9.55 (1H, s, NH), 7.80–7.70 (4H, m, ArH), 7.65–7.50 (6H, m, ArH),
7.35 (2H, d, J=4.7 Hz, ArH), 7.25–7.05 (5H, m, ArH), 5.30 (1H, s,
CH); EIMS: m/z 409 (M+). Analysis. calculated for C30H19NO: C,
88.00; H, 4.68; N, 3.42. Found: C, 88.11; H, 4.62; N, 3.39.
7-(4-Bromophenyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]
quinolin-8-one (5): Isolated yield 90%; m.p. 334–335°C; 1H
NMR: δ 10.10 (1H, s, NH), 7.83 (1H, m, ArH), 7.75–7.50 (8H, m,
ArH), 7.35–7.05 (5H, m, ArH), 5.25 (1H, s, CH); EIMS: m/z 437
(M+). Analysis: calculated for C26H16BrNO: C, 71.25; H, 3.68; N,
3.20. Found: C, 71.17; H, 3.65; N, 3.18.
8-(4-Nitrophenyl)-9,14-dihydro-8H-indeno[1,2-b]naphtho[2,3-
1
h]quinolin-9-one (14): Isolated yield 92%; m.p. 366–367°C; H
NMR: δ 10.55 (1H, s, NH), 7.75 (2H, d, J=8.5 Hz, ArH), 7.65–6.90
(14H, m, ArH), 5.40 (1H, s, CH); EIMS: m/z 454 (M+). Analysis:
calculated for C30H18N2O3: C, 79.28; H, 3.99; N, 6.16. Found: C,
79.21; H, 3.90; N, 6.12.
7-(1-Naphthyl)-8,13-dihydro-7H-benzo[h]indeno[1,2-b]quino-
1
lin-8-one (6): Isolated yield 86%; m.p. 280–282°C; H NMR: δ
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124 S. Damavandi and R. Sandaroos
8-[4-(2-Furyl)phenyl]-9,14-dihydro-8H-indeno[1,2-b]
naphtho[2,3-h]quinolin-9-one (15): Isolated yield 84%; m.p.
351–352°C; 1H NMR: δ 9.75 (1H, s, NH), 7.75–7.50 (6H, m, ArH),
7.45–7.10 (8H, m, ArH), 6.35 (1H, t, ArH), 5.25 (1H, s, CH); EIMS:
m/z 399 (M+). Analysis: calculated for C28H17NO2: C, 84.19; H,
4.29; N, 3.51. Found: C, 84.10; H, 4.22; N, 3.48.
Damavandi, S. New approach to the multicomponent one pot syn-
thesis of 2-aryl-1H-phenanthro[9,10-d] imidazoles. Heterocycl.
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catalyzed one-pot Mannich-type reactions: three component syn-
thesis of β-amino carbonyl compounds. Synth. React. Inorg. Met.
Org. Nano Met. Chem. 2011, 41, 266–271.
Heravi, M. M.; Hosseini, T; Derikvand, F.; Beheshtiha, S.;
Bamoharram F. H6P2W18O62.18H2O-catalyzed, three-compo-
nent, one-potsynthesis of indeno[1,2-b]quinoline-7-one deriva-
tives. Synth. Commun. 2010, 40, 2402–2406.
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organic reactions II: a review of the literature Nov 95–Nov 96.
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8-(4-Methoxyphenyl)-9,14-dihydro-8H-indeno[1,2-b]
naphtho[2,3-h]quinolin-9-one (16): Isolated yield 86%; m.p.
343–345°C; 1H NMR: δ 9.95 (1H, s, NH), 7.75–7.25 (16H, m, ArH),
5.60 (1H, s, CH), 3.65 (3H, s, OMe); EIMS: m/z 439 (M+). Analysis:
calculated for C31H21NO2: C, 84.72; H, 4.82; N, 3.19. Found:
C, 84.66; H, 4.77; N, 3.14.
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o-trifluoroacetyl anilines: one-pot synthesis of 4-trifluorometh-
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9449–9453.
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substituted 1,2-dihydroquinolines via a modified Skraup reac-
tion. Tetrahedron Lett. 2002, 43, 3907–3910.
N-(1-Anthracyl)-4-nitrobenzaldimine (A)
To a solution of 4-nitrobenzaldehyde (1 mmol) in ethanol (10 ml),
1-aminonaphthalene (1 mmol) and a trace amount of p-toluenesulfo-
nic acid were added. The mixture was heated under reflux for 2h. The
reaction mixture was cooled and the precipitate was filtered and crys-
tallized from acetonitrile. The yield was 90%; m.p. 155–157°C; IR: ν
3010, 2873, 1670, 1515, 1335, 1010, 832, 720 cm-1; 1H NMR: δ 8.35
(1H, s, CHN), 8.08 (2H, d, J=5.4 Hz, ArH), 7.90–7.80 (3H, m, ArH),
7.75–7.55 (4H, m, ArH), 7.50–7.38 (2H, m, ArH), 7.20 (1H, m, ArH),
7.05 (1H, t, J=7.3 Hz, ArH). Analysis: calculated for C21H14N2O2: C,
77.29; H, 4.32; N, 8.58. Found: C, 77.19; H, 4.29; N, 8.54.
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An efficient one-pot, three-component synthesis of indeno[1,2-b]
quinoline-9,11(6H,10H)-dione, acridine-1,8(2H,5H)-dione, and
quinoline-3-carbonitrile derivatives from enaminones. Org.
Biomol. Chem. 2006a, 4, 3664–3673.
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ple procedure for the synthesis of 4-aza-podophyllotoxin deriva-
tives in water under microwave irradiation conditions. Synlett
2006b, 17, 2785–2790.
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component green synthesis of N-arylquinoline derivatives in ionic
liquid [Bmimþ][BF4]: Reactions of arylaldehyde, 3-arylamino-5-
,5-dimethylcyclohex-2-enone and active methylene compounds.
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2-(4-Nitrobenzylidenyl)-1,3-indanedione (B)
A solution of 1,3-indanedione (1 mmol) and 4-nitrobenzaldehyde
(1 mmol) in ethanol (10 ml) was heated under reflux for 1 h. The
resultant precipitate was filtered, washed with ether and crystallized
from acetonitrile. The yield was 80%; m.p. 181–183°C; IR: ν 2915,
1665, 1570, 1405, 1185, 940, 810 cm-1; 1H NMR: δ 8.55 (1H, s, CH),
8.10 (2H, d, J=6.4 Hz, ArH), 7.85–7.50 (4H, m, ArH), 7.45–7.20
(2H, m, ArH). Analysis: calculated for C16H9NO4: C, 68.82; H, 3.25;
N, 5.02. Found: C, 68.64; H, 3.20; N, 4.58.
Acknowledgements
Wang, X. S.; Li, Q.; Wu, J. R.; Li, Y. L.; Yao, C. S.; Tu, S. J. An effi-
cient and highly selective method for the synthesis of 3-arylben-
zoquinoline derivatives catalyzed by iodine via three component
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The authors gratefully acknowledge the partial financial support
from the Ferdowsi University of Mashhad, Iran.
Zhu, J.; Bienaime, H. Multicomponent Reactions. Wiley-VCH,
Weinheim, 2005.
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Received May 29, 2011; accepted July 1, 2011
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