One-pot, fast cyclopropanation reaction of indandione with various aldehydes in the presence of cyanogen bromide and trimethylamine

Article abstract of DOI:10.1002/jccs.201800419

A new, fast, and easy one-pot cyclopropanation reaction of aromatic and aliphatic aldehydes with 1H-indene-1,3(2H)-dione and cyanogen bromide (BrCN) was developed for synthesizing 3′-(aryl[alkyl])-dispiro[indan-2,1′-cyclopropane-2′,2′′-indan]-1,1′′,3,3′′-

Full text of DOI:10.1002/jccs.201800419

Received: 5 November 2018
DOI: 10.1002/jccs.201800419
Accepted: 21 March 2019
A R T I C L E
One-pot, fast cyclopropanation reaction of indandione with
various aldehydes in the presence of cyanogen bromide and
trimethylamine
Michael Aalinejad | Nader Noroozi Pesyan
Department of Organic Chemistry, Faculty
of Chemistry, Urmia University, Urmia, Iran
Abstract
A new, fast, and easy one-pot cyclopropanation reaction of aromatic and aliphatic
Correspondence
Nader Noroozi Pesyan, Department of
Organic Chemistry, Faculty of Chemistry,
Urmia University, Urmia 57159, Iran.
aldehydes with 1H-indene-1,3(2H)-dione and cyanogen bromide (BrCN) was
developed for synthesizing 30-(aryl[alkyl])-dispiro[indan-2,10-cyclopropane-20,200-
indan]-1,100,3,300-tetrone in excellent yields in a short time (about 15 s) under basic
Email: n.noroozi@urmia.ac.ir
1
media. All structures were characterized using IR, H NMR, and 13C NMR spec-
troscopy techniques.
Funding information
Urmia University Research Council
K E Y W O R D S
cyanogen bromide, cyclopropane, indandione, one-pot reaction
The cyclopropyl group is a significant structural subject
in many herbal compounds, showing antibacterial, antiviral,
and some enzyme inhibition activities.[4–11] The techniques
of cyclopropane synthesis have been distributed into two
main groups: namely intramolecular cyclization and addition
among alkenes and carbenes. On the other hand, Michael
Initiated Ring Closer (MIRC) is an essential synthetic
method for cyclization.[3]
1 | INTRODUCTION
Indandione is an important initial material that has drawn
great attention in numerous organic transformation because
of its qualities, such as low price, easy handling, and eco-
friendliness usually affording the conforming products in
excellent yields.[1]
The growth of methods that permit access to structurally
diverse cyclopropane-containing compounds is a significant
goal in synthetic organic chemistry. Truly, cyclopropanes
are the most suitable class of multipurpose building blocks
and numerous biologically active molecules contain the
cyclopropane part. The construction of cyclopropane rings is
of great significance for their intrinsic value of key interme-
diates for more transformations.[2] In multicomponent reac-
tions (MCRs), two or more reactants come together in a
solitary reaction to give a product with atom economy. This
reaction is becoming increasingly significant in organic and
pharmaceutical chemistry because it permits to gain
extremely sophisticated polyfunctional molecules through
simple one-pot procedures. In the past decade, industrial and
theoretical research has made dominant MCR strategies into
one of the most effective and cost-effective tools for combi-
natory synthesis.[3]
BrCN is very suitable reagent in organic synthesis.[12,13] It is
useful and capable substance for the synthesis of
cyanamides,[12] cyanates,[13] and also used for selective partition
of the methionyl peptide bonds in ribonuclease.[14] Moreover,
this compound is a suitable brominating and cyanating agent for
the bromination and cyanation of imidazoles.[15] More recently,
good results were obtained from reaction of cyanogen bromide
with aldehyde derivatives and malononitrile,[3,16] ethyl
cyanoacetate,[4] dispiro cyclopropanation of Meldrum's
acids[17,18] by our research team.
Based on these conceptions, we have accomplished a
new and a very fast one-pot alteration of aldehydes and
1,3-indandione to 30-(aryl and/or alkyl)-dispiro[indan-2,10-
cyclopropane-20,200-indan]-1,100,3,300-tetrone in the presence
of BrCN in excellent yields in a few seconds under alkali
conditions.
© 2019 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2019;1–8.
http://www.jccs.wiley-vch.de
1

2
AALINEJAD AND NOROOZI PESYAN
method in the literature. Salts 4 were isolated and character-
ized using spectroscopic techniques (Scheme 3).
2 | RESULTS AND DISCUSSION
Representatively, the proposed mechanism for the synthe-
sis of 3b is shown in Scheme 2. Compound 3b was obtained
through path a and no paths b and c were occurred. First, the
Knoevenagel condensation of aldehyde 1b with 2 yielded
2-benzylidene indandione (8b) then the nucleophilic attack of
4a' on the β-carbon position of 8b as an α,β-unsaturated com-
pound afforded an intermediate triethylammonium 3-bromo-
2-phenyl-1,3-indandionepropan-1-ide (9b). Intramolecular C-
attack of carbanion on carbon atom containing bromine atom
(path a) as an electrophile (pushing the bromide ion out) pro-
duced 3b (Scheme 2).
This article describes a new one-pot reaction of aldehydes
(1) with 1,3-indandione (2) and BrCN to give 30-(aryl and/or
alkyl)-dispiro[indan-2,10-cyclopropane-20,200-indan]-
1,100,3,300-tetrone in the presence of trimethylamine (Et3N)
and/or sodium ethoxide (EtONa) in excellent yields in a very
short time (15 s) (Scheme 1).
When 1,3-indandione 2 reacted with aldehydes under
BrCN condition, the only product of cyclopropane is
obtained in good yields and no trace of dihydrofuran com-
pounds was obtained. The results are summarized in
Table 1. As shown in Table 1, the aromatic and aliphatic
aldehydes could react with 2 and gave the corresponding
cyclopropanes as the exclusive products in good yields.
Besides, Wang et al reported the formation of the mixtures
of cyclopropane and spiro dihydrofuran products in the reac-
tion of 2 with various aldehydes in the presence of I2/
DMAP.[2] Instead, in our method, the sole spiro cyclopro-
pane derivatives were obtained and this is the main advan-
tage of the present work. Interestingly, the reaction of
formaldehyde with 2 was very successful as it shows two
symmetry planes in the formula structure similar to the
cyclopropane derived from Medrum's acid.[17]
The 13C NMR spectra of compounds 3 were the best tool
for the confirmation of the structures of 3. All compounds
3 with the exception of 3a, which was derived from formal-
dehyde, showed two peaks for carbonyl carbon atoms.
Instead, 3a derived from formaldehyde showed a distinct
peak due to having two planes of symmetry (Figure 2).
3 | EXPERIMENTAL
3.1 | Subheading
The structures of compounds were drawn using ChemDraw
Professional 15.0 version software. Melting points were mea-
sured using a digital melting point device. IR spectra were deter-
mined in the region 4,000–400 cm−1 on a NEXUS 670 FT IR
In these reactions, the salt 4 plays a major role in the syn-
thesis of 3. The structures of salts 4a'–4b' are shown in
Figure 1. According to our previous reported mechanisms
for the formation of the salts 10[3] and 11,[19–25] a representa-
tive proposed reaction mechanism for the formation of salt
4a' is shown in Scheme 3. The salt of 7a' was formed in the
presence of Et3N and in the absence of BrCN (path b).
Instead, in the presence of BrCN and Et3N, salt of 4a' was
formed through intermediates 5 and 6 (Scheme 3). We have
examined the reaction of 2 with BrCN in the presence of
Et3N and in the absence of aldehydes 1, so that salt 4a' was
isolated in excellent yield. These experiments confirmed the
major role of 4 in the synthesis of 3. According to our sea-
rch, there is no report about synthesis of salts 4 using our
1
spectrometer using KBr pellets. The H and 13C NMR spectra
were verified on a Bruker 300 FT-NMR at 300 and 75 MHz,
respectively (Urmia University, Urmia, Iran). 1H and 13C NMR
spectra were gained on solution in DMSO-d6 and/or CDCl3 as
NMR solvent. The data are reported as: s = singlet, d = dou-
blet, t = triplet, q = quartet, m = multiplet, or unresolved,
bs = broad singlet, and coupling constant(s) in Hz, integration.
1
The H and 13C NMR spectra were investigated by MestReC
software using original spectra files. Cyanogen bromide was
synthesized based on reported references.[26] Aliphatic and aro-
matic (di)aldehydes, Et3N, and solvents were bought from
Merck and Aldrich without more purification.
3.1.1 | General procedure for the synthesis of
30-(aryl[alkyl])-dispiro[indan-2,10-
cyclopropane-20,200-indan]-1,100,3,300-tetrone (3)
In a 25 mL round bottom flask equipped with a magnetic
stirrer and an ice bath, formaldehyde (1.0 mmol) and
indandione (2.0 mmol) were dissolved in 5 mL MeOH, the
appropriate base (1.33 mmol, see Table 1) was added, and
then cyanogen bromide (1.2 mmol) was added to the solution
at 0ꢀC to room temperature. The teflon-faced screw cap tube
prevents the evaporation of cyanogen bromide. A cream color
SCHEME 1 Synthesis of 3 in the reaction of aldehyde 1 with
1,3-indandione 2 in the presence of BrCN under alkali conditions

AALINEJAD AND NOROOZI PESYAN
3
TABLE 1 The structure of reactant, products, and reaction time and yields
Entry Aldehyde (1)
Product (3)
Base
(mmol)
Reaction time (sec),
yield (%)
Melting
point (ꢀC)
1
2
CH2O (a)
EtONa
(1.33)
15, 100
238-241
EtONa
(1.33)
15, 85
207-208
210-212[2]
(b)
3
Et3N (1.33)
15, 100
205-207
198-199[2]
(c)
4
Et3N (1.33)
15, 100
227-228
214-216[2]
(d)
5
Et3N
(1.33)
15, 95
177-179
176-178[2]
(e)
6
Et3N
(1.33)
15, 95
187-189
194-195[2]
(f)

4
AALINEJAD AND NOROOZI PESYAN
TABLE 1 (Continued)
Entry Aldehyde (1)
Product (3)
Base
(mmol)
Reaction time (sec),
yield (%)
Melting
point (ꢀC)
7
Et3N (1.33)
15, 100
195-197
193-194[2]
(g)
8
Et3N (1.33)
15, 90
198-200
207-210[2]
(h)
9
Et3N (1.33)
15, 85
172-173
180-181[2]
(i)
10
Et3N (1.33)
15, 80
170-171
178-180[2]
(j)
11
Et3N (1.33)
15, 78
168-170
(k)
12
Et3N (1.33)
15, 75
198-199
192-194[2]
(l)

AALINEJAD AND NOROOZI PESYAN
5
FIGURE 1 Formula structure of salts 4a0, 4b0 (this work), 10,[3]
and 11[14,19–25]
solid was precipitated after 15 s, after about 3 min it was fil-
tered off, washed with cool EtOH (3× 3 mL) and H2O, rec-
rystallized in minimum hot EtOH, filtered off and dried as a
colorless crystalline solid (0.236 g, 100% yield).
3.1.2 | Synthesis of dispiro[indene-2,10-
cyclopropane-20,200-indene]-1,100,3,300-
tetraone (3a)
SCHEME 3 Proposed mechanism for the formation of 4a0
Colorless solid; mp 238–241ꢀC; IR (KBr) ν cm−1: 3,072,
2,924, 2,676, 1988, 1,720, 1,589, 1,465, 1,430, 1,372,
1,350, 1,328, 1,240, 1,159, 1,051, 1,013, 968, 931,
886, 826, 768, 749, 710, 680, 556, and 434; 1H NMR
(300 MHz, CDCl3) δ (PPM): 7.91 (d, 2H, Ar–H), 7.27 (d,
2H, Ar–H), and 3.02 (s, 2H, cyclopropane-H); 13C NMR
(75 MHz, CDCl3) δ (PPM): 190.7, 141.7, 135.7, 134.3,
124.4, 122.0, 49.6, and 19.9.
3.1.3 | Synthesis of 30-phenyl-dispiro[indan-
2,10-cyclopropane-20,200-indan]-1,100,3,300-
tetrone (3b)
Colorless solid; mp 207–208ꢀC; IR (KBr) ν cm−1: 3,073,
2,952, 1,719, 1,591, 1,462, 1,412, 1,353, 1,241, 1,156,
1
1,092, 1,031, 748, 693, 565, and 433; H NMR (300 MHz,
CDCl3) δ (PPM): 7.95 (m, 2H, Ar–H), 7.87 (m, 2H, Ar–H),
7.75 (m, 4H, Ar–H), 7.27 (m, 5H, Ar–H), and 4.86 (s, 1H,
cyclopropane-H); 13C NMR (75 MHz, CDCl3) δ (PPM):
191.3, 189.3, 142.5, 141.0, 135.6, 135.5, 130.3, 129.4,
128.2, 128.1, 123.4, 52.3, and 41.2.
3.1.4 | Synthesis of 30-(3-nitrophenyl)-dispiro
[indan-2,10-cyclopropane-20,200-indan]-1,100,3,300-
tetrone (3c)
Colorless solid; mp 205–207ꢀC; IR (KBr) ν cm−1: 3,064,
1,759, 1,719, 1,597, 1,527, 1,485, 1,347, 1,245, 1,157,
1,111, 1,042, 973, 926, 816, 761, 743, 681, 573, and 440;
1H NMR (300 MHz, CDCl3) δ (PPM): 8.21 (d, 1H, Ar-H),
8.20 (s, 1H, Ar–H), 8.00 (m, 2H, Ar–H), 7.93 (m, 2H, Ar–
H), 7.84 (m, 4H, Ar–H), 7.66 (d, 1H, Ar–H), 7.53 (t, 1H,
Ar–H), and 4.86 (s, 1H, cyclopropane-H); 13C NMR
(75 MHz, CDCl3) δ (PPM): 190.4, 189.1, 148.0, 142.4,
141.1, 135.9, 135.8, 131.7, 129.1, 125.6, 123.6, 123.5,
123.2, 51.2, and 39.3.
SCHEME 2 Proposed reaction mechanism for the formation of
full-substituted cyclopropanes

6
AALINEJAD AND NOROOZI PESYAN
190.9, 189.2, 142.4, 141.0, 135.7, 135.6, 134.0, 131.7,
128.4, 128.0, 123.4, 123.3, 52.1, and 40.2.
3.1.7 | Synthesis of 30-(4-bromophenyl)-dispiro
[indan-2,10-cyclopropane-20,200-indan]-1,100,3,300-
tetrone (3f)
Colorless solid; mp 187–189ꢀC; IR (KBr) ν cm−1: 2,939,
1,754, 1,720, 1,595, 1,491, 1,423, 1,350, 1,329, 1,242,
1,155, 1,115, 1,043, 1,012, 966, 893, 822, 750, 697, 566,
1
495, and 438; H NMR (300 MHz, CDCl3) δ (PPM): 7.98
(m, 2H, Ar–H), 7.92 (m, 2H, Ar–H), 7.82 (m, 4H, Ar–H),
7.46 (m, 2H, Ar–H), 7.19 (d, 2H, Ar–H), and 4.77 (s, 1H,
cyclopropane-H); 13C NMR (75 MHz, CDCl3) δ (PPM):
190.9, 189.2, 142.4, 141.0, 135.7, 135.6, 132.1, 131.4,
128.6, 123.5, 123.4, 122.3, 52.2, and 40.4.
3.1.8 | Synthesis of 30-(2,4-dichlorophenyl)-
dispiro[indan-2,10-cyclopropane-20,200-indan]-
1,100,3,300-tetrone (3g)
Colorless solid; mp 195–197ꢀC; IR (KBr) ν cm−1: 3,073,
2,943, 1,760, 1,722, 1,596, 1,471, 1,427, 1,349, 1,327,
1,242, 1,157, 1,124, 1,034, 976, 914, 818, 763, 747, 575,
1
and 435; H NMR (300 MHz, CDCl3) δ (PPM): 7.98 (m,
FIGURE 2 Two planes of symmetry in 3a (equivalency of four
carbonyl groups) and a plane of symmetry in 3b–3l
2H, Ar–H), 7.93 (m, 2H, Ar–H), 7.83 (m, 4H, Ar–H), 7.43
(d, 1H, Ar–H), 7.40 (d, 1H, Ar–H), 7.18 (d, 1H, Ar–H),
and 4.74 (s, 1H, cyclopropane-H); 13C NMR (75 MHz,
CDCl3) δ (PPM): 190.6, 189.1, 142.4, 141.1, 135.8, 135.7,
132.4, 132.3, 132.2, 130.1, 129.9, 129.8, 123.5, 52.0,
and 39.4.
3.1.5 | Synthesis of 30-(4-nitrophenyl)-dispiro
[indan-2,10-cyclopropane-20,200-indan]-1,100,3,300-
tetrone (3d)
Colorless solid; mp 227–228ꢀC; IR (KBr) ν cm−1: 2960,
1,757, 1,721, 1,596, 1,517, 1,345, 1,243, 1,158, 1,111,
853, 747, 699, 566, and 438; 1H NMR (300 MHz, CDCl3) δ
(PPM): 8.20 (d, 2H, Ar–H), 8.01 (m, 2H, Ar–H), 7.95 (m,
2H, Ar–H), 7.85 (m, 4H, Ar–H), 7.49 (d, 2H, Ar–H), and
4.86 (s, 1H, cyclopropane-H); 13C NMR (75 MHz, CDCl3)
δ (PPM): 190.4, 189.1, 147.6, 142.3, 141.1, 137.2, 135.9,
135.8, 131.5, 123.6, 123.5, 123.3, 51.9, and 39.5.
3.1.9 | Synthesis of 30-(4-cyanophenyl)-dispiro
[indan-2,10-cyclopropane-20,200-indan]-1,100,3,300-
tetrone (3h)
Colorless solid; mp 198–200ꢀC; IR (KBr) ν cm−1: 2,955,
2,223, 1,755, 1,720, 1,591, 1,353, 1,242, 1,155, 1,125,
966, 896, 832, 749, 573, and 434; 1H NMR (300 MHz,
CDCl3) δ (PPM): 7.99 (m, 2H, Ar–H), 7.92 (m, 2H, Ar–H),
7.84 (m, 4H, Ar–H), 7.63 (d, 2H, Ar–H), 7.44 (d, 2H, Ar–
H), and 4.83 (s, 1H, cyclopropane-H); 13C NMR (75 MHz,
CDCl3) δ (PPM): 190.5, 189.1, 142.4, 141.1, 135.9, 135.8,
135.2, 131.9, 131.3, 123.6, 123.5, 118.7, 112.1, 52.0,
and 40.0.
3.1.6 | Synthesis of 30-(4-chlorophenyl)-dispiro
[indan-2,10-cyclopropane-20,200-indan]-1,100,3,300-
tetrone (3e)
Colorless solid; mp 177–179ꢀC; IR (KBr) ν cm−1: 2,955,
2,925, 1,758, 1,720, 1,593, 1,494, 1,402, 1,352, 1,329,
1,243, 1,157, 1,111, 1,016, 895, 827, 756, 709, 566, and
3.1.10 | Synthesis of 30-(4-methylphenyl)-
dispiro[indan-2,10-cyclopropane-20,200-indan]-
1,100,3,300-tetrone (3i)
Colorless solid; mp 172–173ꢀC; IR (KBr) ν cm−1: 2,925,
1
441; H NMR (300 MHz, CDCl3) δ (PPM): 7.98 (m, 2H,
Ar–H), 7.92 (m, 2H, Ar–H), 7.82 (m, 4H, Ar–H), 7.31 (d,
2H, Ar–H), 7.25 (d, 2H, Ar–H), and 4.79 (s, 1H,
cyclopropane-H); 13C NMR (75 MHz, CDCl3) δ (PPM):
1,755, 1,720, 1,595, 1,424, 1,351, 1,245, 1,159, 1,119,

AALINEJAD AND NOROOZI PESYAN
7
1
1,041, 966, 828, 775, 752, 571, 474, and 434; H NMR
(300 MHz, CDCl3) δ (PPM):7.97 (m, 2H, Ar–H), 7.91 (m,
2H, Ar–H), 7.79 (m, 4H, Ar–H), 7.17 (d, 2H, Ar–H), 7.14
(d, 2H, Ar–H), 4.84 (s, 1H, cyclopropane-H), and 2.36 (s,
3H, CH3); 13C NMR (75 MHz, CDCl3) δ (PPM): 191.4,
189.3, 142.5, 141.0, 137.8, 135.6, 135.4, 130.2, 129.0,
126.3, 123.4, 52.5, 41.4, and 21.4.
136.5, 135.9, 135.8, 135.7, 131.2, 129.5, 123.5, 123.4,
52.1, and 40.3.
4 | CONCLUSIONS
The one-pot cyclopropanation reaction of aromatic and ali-
phatic aldehydes with 1H-indene-1,3(2H)-dione and cyano-
gen bromide (BrCN) was developed that gives excellent
yields in a short time (about 15 s) under basic media.
3.1.11 | Synthesis of 30-(4-methoxyphenyl)-
dispiro[indan-2,10-cyclopropane-20,200-indan]-
1,100,3,300-tetrone (3j)
ACKNOWLEDGMENTS
Colorless solid; mp 170–171ꢀC; (KBr) ν cm−1: 3,073,
2,952, 1859, 1836, 1,720, 1,532, 1,457, 1,345, 1,242,
1,109, 1,039, 977, 926, 816, 749, 681, 571, and 459;
1H NMR (300 MHz, CDCl3) δ (PPM): 7.95 (d, 2H, Ar–
H), 7.90 (m, 2H, Ar–H), 7.77 (m, 4H, Ar–H), 7.25 (d,
2H, Ar–H), 6.86 (d, 2H, Ar–H), 4.82 (s, 1H,
cyclopropane-H), and 3.82 (s, 3H, –OCH3); 13C NMR
(75 MHz, CDCl3) δ (PPM): 191.2, 189.4, 142.3, 140.9,
136.5, 135.6, 134.1, 132.3, 130.5, 124.4, 122.0, 121.1,
114.0, 113.1, and 52.4.
We thank the Urmia University Research Council for
supporting this work.
ORCID
Nader Noroozi Pesyan https://orcid.org/0000-0002-4257-
434X
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[23] N. Noroozi Pesyan, M. Jalilzadeh, J. Chem. Sci. Tech. 2012, 1, 1.
[24] N. Noroozi Pesyan, A. Shokr, M. Behroozi, E. S¸ahin, J. Iran.
Chem. Soc. 2013, 10, 565.
3.1.13 | Synthesis of 30-(4-formylphenyl)-
dispiro[indan-2,10-cyclopropane-20,200-indan]-
1,100,3,300-tetrone (3l)
Colorless solid; mp 198–199ꢀC; IR (KBr) ν cm−1: 2,959,
1,756, 1,721, 1,700, 1,604, 1,350, 1,243, 1,158, 1,105,
1,037, 966, 896, 831, 787, 750, 687, 566, and 436; 1H
NMR (300 MHz, CDCl3) δ (PPM): 10.0 (s, 1H, CHO),
7.99 (m, 2H, Ar–H), 7.92 (m, 2H, Ar–H), 7.86 (d, 2H,
Ar–H), 7.83 (m, 4H, Ar–H), 7.47 (d, 2H, Ar–H), and
4.87 (s, 1H, cyclopropane-H); 13C NMR (75 MHz,
CDCl3) δ (PPM): 191.8, 190.7, 189.1, 142.4, 141.1,

8
AALINEJAD AND NOROOZI PESYAN
[25] N. Noroozi Pesyan, A. Shokr, A. Gharib, T. Tunç, E. S¸ahin,
J. Chin. Chem. Soc. 2015, 62, 234.
[26] W. W. Hartman, E. E. Dreger, Org. Synth. Coll. 1943, 2, 150.
How to cite this article: Aalinejad M, Noroozi
Pesyan N. One-pot, fast cyclopropanation reaction of
indandione with various aldehydes in the presence of
cyanogen bromide and trimethylamine. J Chin Chem
Soc. 2019;1–8. https://doi.org/10.1002/jccs.
201800419
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