One-pot synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11, 3′-indoline]-triones

Article abstract of DOI:10.1002/jhet.412

(Chemical Equation Presented) A one-pot and pseudo four-component synthesis of spiro[diindeno[1,2-b:2′,1′-e]pyridine-11,3′-indoline]- trione derivatives by cyclo-condensation reaction of isatins, 1,3-indandione, and ammonium acetate in refluxing acetic acid is reported.

Full text of DOI:10.1002/jhet.412

September 2010
One-Pot Synthesis of Spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-
indoline]-triones
1031
Ramin Ghahremanzadeh,a,b Fatemeh Fereshtehnejad,a and Ayoob Bazgira*
aDepartment of Chemistry, Shahid Beheshti University, G.C. Tehran 1983963113, Iran
bNanobiotechnology Research Center, Avicenna Research Institute, ACECR, Tehran, Iran
*E-mail: a_bazgir@sbu.ac.ir
Received October 24, 2009
DOI 10.1002/jhet.412
Published online 13 July 2010 in Wiley Online Library (wileyonlinelibrary.com).
A one-pot and pseudo four-component synthesis of spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-indo-
line]-trione derivatives by cyclo-condensation reaction of isatins, 1,3-indandione, and ammonium acetate
in refluxing acetic acid is reported.
J. Heterocyclic Chem., 47, 1031 (2010).
INTRODUCTION
medicinal agents [18], and some of indolines, spiro-
annulated with heterocycles in the 3-position, have
shown high biological activity [19–21]. The spirooxin-
dole system is the core structure of many pharmacologi-
cal agents and natural alkaloids [22–24]. Therefore, a
number of methods have been reported for the prepara-
tion of spirooxindole fused heterocycles [25].
Multicomponent reactions (MCRs) have been fre-
quently used by synthetic chemists as a facile means to
generate molecular diversity from bifunctional substrates
that react sequentially in an intramolecular fashion [1,2].
Devising such types of MCRs that achieve the formation
of multiple bonds in a single operation is one of the
major challenges in modern organic synthesis [3,4]. As
such processes avoid time consuming and costly purifica-
tion processes, as well as protection–deprotection steps,
they are inherently more environmentally benign and
atom economic [5]. They provide a powerful tool toward
the one-pot synthesis of diverse and complex compounds
as well as small and drug-like heterocycles [6].
As part of our continuing efforts on the synthesis of
biologically active heterocyclic compounds [26], we
recently described an efficient synthesis of spiropyrimi-
doquinoline-pyrrolopyrimidines and spiroindoline-pyri-
dodipyrimidines via a condensation reaction between
amino-uraciles and isatines [27]. We have also devel-
oped an efficient synthesis of spiro[dibenzo[b,i]xan-
thene-13,30-indoline]-pentaones via a reaction of isatins
and 2-hydroxy-naphthoquinone in water [28].
Indenone-fused heterocycles represent important bio-
logical and medicinal scaffolds. Thus, the indenopyri-
dine skeleton is present in the 4-azafluorenone group of
alkaloids, represented by its simplest member onychnine
(Fig. 1) [7]. Indenopyrazoles (A) and indenopyridazines
(B) have been investigated as cyclin-dependent kinase
[8] and selective monoamine oxidase B (MAO-B) [9]
inhibitors, respectively.
Considering the important biological properties of spi-
rooxindole fused heterocycles, we report herein a one-
pot, pseudo four-component synthesis of spiro[diin-
deno[1,2-b:20,10-e]pyridine-11,30-indoline]-triones
4
through a one-pot condensation reaction of 1,3-indan-
dione 1, ammonium acetate 2 and isatins 3 in refluxing
acetic acid (Scheme 1).
Further, indenopyridines (C) exhibit cytotoxic [10],
phosphodiesterase inhibitory [11], adenosine A2a recep-
tor antagonistic [12], anti-inflammatory/antiallergic [13],
coronary dilating [14], and calcium modulating activities
[15]. These compounds have also been investigated for
the treatment of hyperlipoproteinemia and arteriosclero-
sis [16] as well as neurodegenerative diseases [17].
Indole and indoline fragments are important moieties
of a large number of a variety of natural products and
RESULTS AND DISCUSSION
In a pilot experiment, a mixture of 1,3-indandione 1,
ammonium acetate 2, and isatin 3a at refluxing acetic
acid were stirred to afford the 5H-spiro[diindeno[1,2-b:
20,10-e]pyridine-11,30-indoline]-20,10,12-trione 4a in 87%
for 4 h.
C
V
2010 HeteroCorporation

1032
R. Ghahremanzadeh, F. Fereshtehnejad, and A. Bazgir
Vol 47
Table 1
Synthesis of spiro[diindenopyridine-indoline]-triones 4.
Product 4
R
X
Yield (%)
a
b
c
d
e
f
g
h
i
H
Me
Et
PhCH2
H
H
H
87
85
82
80
91
88
79
92
76
78
79
77
H
H
Br
Figure 1. Representatives of important indenone-fused heterocycles
H
H
Me
F
Encouraged by this success, we extended this reaction
of 1,3-indandione 1 and ammonium acetate 2 with a
range of other isatins 2b-l under similar conditions, fur-
nishing the respective 5H-spiro[diindeno[1,2-b:20,10-e]pyr-
idine-11,30-indoline]-20,10,12-triones 4b-l in good yields.
The optimized results are summarized in Table 1. We
have shown that the use of a wide diversity of substitu-
ents in isatins 3 in this reaction makes possible the syn-
thesis of libraries under similar circumstances.
1H and 13C NMR spectra of the crude products
clearly indicated the formation of spirooxindol fused
diindenopyridines 4. The nature of these compounds as
2:1:1 adducts was apparent from their mass spectra,
which displayed, in each case, the molecular ion peak at
appropriate m/z value. Compounds 4a–l are stable solids
whose structures were established by IR, 1H and 13C
NMR spectroscopy and elemental analysis.
H
Me
Et
Me
Et
NO2
Br
j
k
l
Br
NO2
NO2
ninhydrine 9 and obtained 5H-spiro[diindeno[1,2-b:20,10-
e]pyridine-11,20-indene]-10,30,10,12-tetraone 10 in 78%
yield (Scheme 3).
For the investigation of the reaction mechanism, it is
notable that when the 1,3-indandione 1, ammonium ace-
tate 2, and isatin 3a were reacted for 2 h, the intermedi-
ate 6 were isolated and characterized by spectroscopic
methods. When intermediate 6 was reacted with NH4OAc 2
under the same reaction conditions, the product 4a was
obtained in 83% yield (Scheme 2).
In conclusion, we have demonstrated an efficient and
simple method for the preparation of some spirooxindole
fused heterocycles using readily available starting mate-
rials. Prominent among the advantages of this new
method are operational simplicity, good yields, and easy
work-up procedures employed. Moreover, it is worth
noting that two CAC and one two CAN bonds were
formed with concomitant creation of a spirooxindoles in
this one-pot, pseudo four-component process.
Therefore, the formation of products 4 can be rational-
ized via initial addition of 1,3-indanedione 1 to the isatins
3 to yield intermediate 5, which reacted further with
another molecule of 1. Finally, reaction of ammonium ac-
etate 2 with the intermediate 6, followed by cyclization
afforded the corresponding product 4 (Scheme 3).
EXPERIMENTAL
As expected, when the isatins 3 was replaced by ace-
naphthylene-1,2-dione 7, 2H,50H-spiro[acenaphthylene-
Melting points were measured on an Elecrtothermal 9100
apparatus. Mass spectra were recorded on a FINNIGAN-MAT
8430 mass spectrometer operating at an ionization potential of
1,110-diindeno[1,2-b:20,10-e]pyridine]-2,100,120-trione
8
1
70 eV. H and 13C NMR spectra were recorded on a BRUKER
was obtained in 82% yield under the same reaction con-
ditions (Scheme 4).
DRX-300 AVANCE spectrometer at 300.13 and 75.47 MHz,
respectively. IR spectra were recorded using a Shimadzu IR-
470 apparatus. Elemental analyses were performed using a
Heracus CHN-O-Rapid analyzer.
To further explore the potential of this protocol for
spirofused heterocycle synthesis, we investigated reac-
tion of 1,3-indandione 1 and ammonium acetate 2 with
Scheme 2
Scheme 1
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

September 2010 One-Pot Synthesis of Spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-indoline]-triones
1033
50-Methyl-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-
Scheme 3
indoline]-20,10,12-trione (4f). Red powder (88%); m.p >
300ꢀC. IR (KBr) (mmax/cmꢁ1): 3169, 2996, 1682, 1645. MS
(EI, 70 eV) m/z: 416 (Mþ). 1H NMR (300 MHz, DMSO-d6):
dH 2.13 (s, 3H, CH3), 6.72–7.76 (m, 11H, ArH), 10.53 (s, 1H,
NH), 11.60 (s, 1H, NH). Anal. Calcd for C27H16N2O3: C,
77.87; H, 3.87; N, 6.73%. Found: C, 77.74; H, 3.77; N, 6.64%.
50-Fluoro-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-
indoline]-20,10,12-trione (4g). Red powder (79%); m.p >
300ꢀC. IR (KBr) (mmax/cmꢁ1): 3048, 2901, 1681, 1640. MS
(EI, 70 eV) m/z: 420 (Mþ). 1H NMR (300 MHz, DMSO-d6):
dH 6.81–7.80 (m, 11H, ArH), 10.63 (s, 1H, NH), 11.66 (s, 1H,
NH). Anal. Calcd for C26H13FN2O3: C, 74.28; H, 3.12; N,
6.66%. Found: C, 74.37; H, 3.06; N, 6.60%.
50-Nitro-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-in-
doline]-20,10,12-trione (4h). Red powder (92%); m.p
>
Because of very low solubility of the products, we cannot
report the 13C NMR data for these products.
300ꢀC. IR (KBr) (mmax/cmꢁ1): 3211, 3048, 1706, 1631, 1600.
1
MS (EI, 70 eV) m/z: 447 (Mþ). H NMR (300 MHz, DMSO-
Typical procedure for the preparation of 5H-Spiro[diin-
deno[1,2-b:20,10-e]pyridine-11,30-indoline]-20,10,12-trione
(4a). A mixture of 1,3-indandione 1a (0.30 g, 2 mmol), ammo-
nium acetate 2 (0.46 g, 3 mmol), and isatin 3a (0.15 g, 1
mmol) in refluxing (5 mL) was stirred for 4 h (the progress of
the reaction was monitored by TLC). After completion, the
reaction mixture was filtered and the precipitate washed with
water (10 mL) and recrystallized by EtOH to afford the pure
product 4a as red powder (87%); m.p >300ꢀC (dec). IR (KBr)
(mmax/cmꢁ1): 3169, 2996, 1694, 1672, 1631. MS (EI, 70 eV)
d6): dH 7.07–8.15 (m, 11H, ArH), 11.36 (s, 1H, NH), 11.93 (s,
1H, NH). Anal. Calcd for C26H13N3O5: C, 69.80; H, 2.93; N,
9.39%. Found: C, 69.72; H, 2.86. N, 9.31%.
50-Bromo-10-methyl-5H-spiro[diindeno[1,2-b:20,10-e]pyri-
dine-11,30-indoline]-20,10,12 -trione (4l). Dark red powder
(76%); m.p > 300ꢀC. IR (KBr) (mmax/cmꢁ1): 2917, 1680,
1640, 1608. MS (EI, 70 eV) m/z: 496 (Mþþ2), 494 (Mþ). H
1
NMR (300 MHz, DMSO-d6): dH 3.21 (s, 3H, NCH3), 7.04-
7.81 (m, 11H, ArH), 11.72 (s, 1H, NH). Anal. Calcd for
C27H15BrN2O3: C, 65.47; H, 3.05; N, 5.66%. Found: C, 65.35;
H, 3.14; N, 5.75%.
1
m/z: 402 (Mþ). H NMR (300 MHz, DMSO-d6): dH 6.83–7.74
(m, 12H, ArH), 10.66 (s, 1H, NH), 11.62 (s, 1H, NH). Anal.
Calcd for C26H14N2O3: C, 77.60; H, 3.51; N, 6.96%. Found:
C, 77.51; H, 3.45; N, 6.88%.
50-Bromo-10-ethyl-5H-spiro[diindeno[1,2-b:20,10-e]pyri-
dine-11,30-indoline]-20,10,12-trione (4j). Red powder (78%);
m.p > 300ꢀC. IR (KBr) (mmax/cmꢁ1): 2931, 1714, 1667. MS
10-Methyl-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-
indoline]-20,10,12-trione (4b). Dark red powder (85%); m.p >
300ꢀC. IR (KBr) (mmax/cmꢁ1): 2926, 1701, 1678, 1617. MS
(EI, 70 eV) m/z: 416 (Mþ). 1H NMR (300 MHz, DMSO-d6):
dH 3.27 (s, 3H, NCH3), 7.07–8.53 (m, 12H, ArH), 11.13 (s,
1H, NH). Anal. Calcd for C27H16N2O3: C, 77.87; H, 3.87; N,
6.73%. Found: C, 77.95; H, 3.80; N, 6.66%.
1
(EI, 70 eV) m/z: 510 (Mþþ2), 508 (Mþ). H NMR (300 MHz,
DMSO-d6): dH 1.21 (bs, 3H, CH3), 3.78 (bs, 2H, NCH2),
7.06–7.79 (m, 11H, ArH), 11.96 (s, 1H, NH). Anal. Calcd for
C28H17BrN2O3: C, 66.03; H, 3.36; N, 5.50%. Found: C, 66.14;
H, 3.30; N, 5.59%.
10-Methyl-50-nitro-5H-spiro[diindeno[1,2-b:20,10-e]pyri-
dine-11,30-indoline]-20,10,12-trione (4k). Red powder (79%);
m.p > 300ꢀC. IR (KBr) (mmax/cmꢁ1): 2996, 1693, 1608. MS
(EI, 70 eV) m/z: 461 (Mþ). 1H NMR (300 MHz, DMSO-d6):
dH 3.33 (s, 3H, NCH3), 7.21–8.29 (m, 11H, ArH), 11.85(s,
1H, NH). Anal. Calcd for C27H15N3O5: C, 70.28; H, 3.28; N,
9.11%. Found: C, 70.19; H, 3.34; N, 9.04%.
10-Ethyl-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-in-
doline]-20,10,12-trione (4c). Red powder (82%); m.p
>
300ꢀC. IR (KBr) (mmax/cmꢁ1): 3219, 2921, 1707, 1652 . MS
(EI, 70 eV) m/z: 430 (Mþ). 1H NMR (300 MHz, DMSO-d6):
dH 1.23–1.27 (m, 3H, CH3), 3.78–3.80 (m, 2H, NCH2), 6.90–
7.80 (m, 12H, ArH), 11.63(1H, s, NH). Anal. Calcd for
C28H18N2O3: C, 78.13; H, 4.21; N, 6.51%. Found: C, 78.01;
H, 4.13; N, 6.62%.
10-Ethyl-50-nitro-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-
11,30-indoline]-20,10,12-trione (4l). Red powder (77%); m.p
> 300ꢀC. IR (KBr) (mmax/cmꢁ1): 2964, 1692, 1645. MS (EI,
70 eV) m/z: 475 (Mþ). 1H NMR (300 MHz, DMSO-d6): dH
10-Benzyl-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-
indoline]-20,10,12-trione (4d). Dark red powder (80%); m.p ¼
270ꢀC IR (KBr) (mmax/cmꢁ1): 3048, 1706, 1666, 1607. MS
(EI, 70 eV) m/z: 492 (Mþ). 1H NMR (300 MHz, DMSO-d6):
dH 5.00 (bs, 2H, NCH2), 6.72–7.81 (m, 17H, ArH), 11.68
(s, 1H, NH). Anal. Calcd for C33H20N2O3: C, 80.47; H, 4.09;
N, 5.69%. Found: C, 80.38; H, 4.01; N, 5.58%.
3
3
1.26 (t, JHH ¼ 6.9 Hz, 3H, CH3), 3.90 (q, JHH ¼ 6.6 Hz,
2H, NCH2), 7.27–8.27 (m, 11H, ArH), 11.83 (s, 1H, NH).
Anal. Calcd for C28H17N3O5: C, 70.73; H, 3.60; N, 8.84%.
Found: C, 70.67; H, 3.55; N, 8.91%.
Scheme 4
50-Bromo-5H-spiro[diindeno[1,2-b:20,10-e]pyridine-11,30-
indoline]-20,10,12-trione (4e). Red powder (91%); m.p >
300ꢀC. IR (KBr) (mmax/cmꢁ1): 3222, 2922, 1698, 1640, 1603.
1
MS (EI, 70 eV) m/z: 482 (Mþþ2), 480 (Mþ). Anal. H NMR
(300 MHz, DMSO-d6): dH 6.84–7.94 (m, 11H, ArH), 10.78
(s, 1H, NH), 11.66 (s, 1H, NH). Calcd for C26H13BrN2O3:
C, 64.88; H, 2.72; N, 5.82%. Found: C, 64.81; H, 2.78; N,
5.89%.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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R. Ghahremanzadeh, F. Fereshtehnejad, and A. Bazgir
Vol 47
2H,50H-Spiro[acenaphthylene-1,110-diindeno[1,2-b:20,10-
[12] Heintzelman, G. R.; Averill, K. M.; Dodd, J. H.; Demarest,
K. T.; Tang Y.; Jackson, P. F. Pat. Appl. Publ. U.S. Pat. 2004,082,578
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e]pyridine]-2,100,120-trione (8). Dark red powder (82%); m.p
> 270ꢀC. IR (KBr) (mmax/cmꢁ1): 3059, 1692, 1640. MS (EI,
70 eV) m/z: 437 (Mþ). 1H NMR (300 MHz, DMSO-d6): dH
7.14–8.29 (m, 15H, ArH, NH). 13C NMR (75 MHz, DMSO-
d6): dC (ppm) 51.5, 11.8, 120.5, 121.2, 121.3, 123.9, 125.0,
128.9, 129.3, 129.7, 130.2, 131.3, 132.9, 133.7, 1373.3, 137.9,
141.3, 143.9, 158.0, 190.5, 205.4. Anal. Calcd for C30H15NO3:
C, 82.37; H, 3.46; N, 3.20%. Found: C, 82.48; H, 3.38; N,
3.29%.
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5H-Spiro[diindeno[1,2-b:20,10-e]pyridine-11,20-indene]-
10,30,10,12-tetraone (10). Dark red powder (78%); m.p >
260ꢀC dec. IR (KBr) (mmax/cmꢁ1): 2922, 1703, 1651. MS (EI,
70 eV) m/z: 415 (Mþ). 1H NMR (300 MHz, DMSO-d6): dH
7.29–8.09 (m, 12H, ArH), 11.94 (s, 1H, NH). Anal. Calcd for
C27H13NO4: C, 78.07; H, 3.15; N, 3.37%. Found: C, 77.97; H,
3.09; N, 3.29%.
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Acknowledgment. We gratefully acknowledge financial
support from the Research Council of Shahid Beheshti
University.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet