untitled


European	Journal	of	Chemistry	3	(3)	(2012)	310‐313	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2012	EURJCHEM	

DOI:10.5155/eurjchem.3.3.310‐313.659	

	
	

	

	

European	Journal	of	Chemistry	
Journal	homepage:	www.eurjchem.com	

	 	 	

Knoevenagel	condensation	of	isatins	with	malononitrile/ethyl	cyanoacetate		
in	the	presence	of	sulfonic	acid	functionalized	silica	(SBA‐Pr‐SO3H)		
as	a	new	nano‐reactor	

Negar	Lashgaria,	Ghodsi	Mohammadi	Ziarania,*,	Alireza	Badieib	and	Parisa	Gholamzadeha	

a	Department	of	Chemistry,	Alzahra	University,	Vanak	Square,	199389‐1176,	Tehran,	Iran	
b	School	of	Chemistry,	College	of	Science,	University	of	Tehran,	14155‐6455,	Tehran,	Iran	

*Corresponding	author	at:	Department	of	Chemistry,	Alzahra	University,	Vanak	Square,	199389‐1176,	Tehran,	Iran.		
Tel.:	+98.21.88041344;	fax:	+98.21.88041344.	E‐mail	address:	gmziarani@hotmail.com	(G.M.	Ziarani).	

	
	

	 	

	 	 	
ARTICLE	INFORMATION	 	 ABSTRACT	
Received:	02	July	2012	
Received	in	revised	form:	12	July	2012	
Accepted:	12	July	2012	
Online:	30	September	2012	

KEYWORDS	

	 The	 Knoevenagel	 condensation	 between	 isatins	 and active	 methylene	 compounds	 like
malononitrile	 and	 ethyl	 cyanoacetate	 to	 prepare	 2‐oxoindolin‐3‐ylidene	 malononitrile/
cyanoacetates	is	described.	The	reactions	occur	in	the	presence	of	sulfonic	acid	functionalized
silica	SBA‐15	(SBA‐Pr‐SO3H)	in	an	aqueous	medium	giving	excellent	yields	of	the	products	in
short	 reaction	 times.	 SBA‐Pr‐SO3H	with	 a	 pore	 size	 of	 6	 nm	 is	 found	 to	 be	 an	 efficient	 and
environmentally	benign	catalyst	for	this	reaction.	

Isatin	
SBA‐Pr‐SO3H	
Nano‐reactor	
Malononitrile	
Knoevenagel	condensation	
2‐Oxoindolin‐3‐ylidene	malononitrile	

	
1.	Introduction	
	

The	Knoevenagel	condensation	is	one	of	the	most	effective	
and	general	reactions	for	the	formation	of	carbon‐carbon	bonds	
[1].	 Furthermore,	 isatin	 has	 been	 used	 extensively	 in	 organic	
synthesis	[2,3].	There	are	various	reports	about	the	application	
of	 isatin	 in	 Knoevenagel	 condensation	 [4‐7].	 Many	 of	 these	
products	present	significant	biological	activities	[8]	or	they	are	
used	in	the	synthesis	of	natural	products	[9,	10].	Malononitrile	
as	 a	 versatile	 reagent	 has	 been	 widely	 used	 in	 condensation	
reactions	to	give	a	variety	of	addition	products	and	heterocyclic	
compounds	 [11].	 Condensation	 of	 malononitrile	 or	 ethyl	
cyanoacetate	 with	 isatin	 and	 its	 derivatives	 to	 prepare	 2‐
oxoindolin‐3‐ylidene	 malononitrile/cyanoacetate	 using	
different	 solvents	 such	as	 ethanol	 [12,13],	methanol	 [14],	 and	
DMSO	 [15]	 has	 been	 studied.	 Microwave	 irradiation	 [16‐18]	
and	grinding	in	the	presence	of	1‐5	equiv.	of	water	[19]	are	the	
other	methods	for	the	synthesis	of	these	compounds.	

Recently,	different	mesoporous	ordered	silicas	such	as	SBA‐
15	 have	 received	 great	 attention	 in	 organic	 synthesis.	 These	
materials	 characterized	 by	 large	 surface	 area,	 hexagonal	
arrangement	 of	 uniform	 pores,	 thick	 walls,	 and	 high	
hydrothermal	 stability.	 Organic	 functional	 groups	 have	 been	
incorporated	 onto	 the	 mesoporous	 silica	 materials	 by	 either	
grafting	 or	 co‐condensation	 methods	 [20,21].	 These	 organic‐
inorganic	hybrids	are	 a	new	class	of	materials	 that	have	been	
extensively	 investigated	in	 the	field	of	catalysis.	Many	sulfonic	
acid	 functionalized	 SBA‐15	 mesoporous	 silicas	 have	 been	
reported	as	catalysts	 in	different	organic	 transformations	[22‐
25].		

Here,	 in	 continuation	 of	 our	 studies,	 on	 the	 application	 of	
heterogeneous	solid	 catalysts	 to	organic	 synthesis	 [26‐30]	we	

report	 our	 results	 on	 the	 condensation	 of	 isatin	 with	
malononitrile	or	ethyl	cyanoacetate	in	the	presence	of	sulfonic	
acid	 functionalized	nanoporous	silica	 (SBA‐Pr‐SO3H)	as	 a	new	
nano‐reactor.	
	
2.	Experimental	
	
2.1.	Instrumentation	
	

All	 chemicals	 were	 obtained	 commercially	 and	 used	
without	 further	 purification.	 The	 IR	 spectra	 were	 recorded	
from	 KBr	 disk	 using	 a	 FT‐IR	 Bruker	 Tensor	 27	 instrument.	
Melting	 points	 were	 measured	 by	 using	 the	 capillary	 tube	
method	with	an	electro	thermal	9200	apparatus.		

The	1H	NMR	spectra	was	run	on	a	Bruker	DPX,	at	250	MHz	
in	CDCl3	 using	TMS	as	 an	 internal	 standard.	GC‐Mass	 analysis	
was	 performed	 on	 a	 GC‐Mass	 model:	 5973	 network	 mass	
selective	 detector,	 GC	 6890	 Agilent.	 SEM	 analysis	 was	
performed	on	a	Philips	XL‐30	field‐emission	scanning	electron	
microscope	operated	at	16	kV	while	TEM	was	carried	out	on	a	
Tecnai	G2	F30	at	300	kV.	

	
2.2.	Synthesis	
	
2.2.1.	Synthesis	and	functionalization	of	SBA‐15	

	
The	 nanoporous	 compound	 SBA‐15	 was	 synthesized	 and	

functionalizaed	according	 to	our	previous	 report	 [28]	 and	 the	
modified	 SBA‐15‐Pr‐SO3H	was	 used	 as	 nanoporous	 solid	 acid	
catalyst	in	the	following	reaction.		
	
	



Lashgari	et	al.	/	European	Journal	of	Chemistry	3	(3)	(2012)	310‐313	 311	
 

	 	

 
	

Scheme	1
	
	
Table	1.	SBA‐Pr‐SO3H	catalyzed	the	synthesis	of	2‐oxoindolin‐3‐ylidene	malononitrile/cyanoacetate	derivatives	3a‐h.	
Entry	 R	 X	 Product Time	(min) Yield	(%) M.p.	(°C)	 M.p.	(Lit.)
1	 H	 CN	 3a	 5	 95	 239‐240	 239	[31]	
2	 Cl	 CN	 3b	 5 90 228‐230	 225‐227	[32]
3	 Br	 CN	 3c	 5 93 236‐238	 220‐221	[19]
4	 NO2	 CN	 3d	 5 90 262‐264	 260‐261	[4]
5	 H	 CO2Et	 3e	 10 90 208‐209	 196‐198	[12]
6	 Cl	 CO2Et	 3f	 15 90 225‐227	 ‐	
7	 Br	 CO2Et	 3g	 15 85 225‐227	 ‐	
8	 NO2	 CO2Et	 3h	 15 85 238‐239	 230‐231	[4]
	
	
Table	2.	Solvent	effects	on	the	synthesis	of	2‐oxoindolin‐3‐ylidene	malononitrile/cyanoacetate	derivatives	3a‐h.	
No.	 Solvent	 Time	(min)	 Yield	of	3a	(%)	
1	 EtOH	 4 90
2	 EtOH/H2O	(1:1)	 10	 80	
3	 H2O	 5	 95	
4	 Neat	(120	°C)	 15 80
	
	
	
2.2.2.	General	procedure	for	the	synthesis	of	2‐oxoindolin‐3‐
ylidene	malononitrile/cyano	acetates	
	

To	 a	mixture	 containing	 isatin	 derivative	1	 (1	mmol)	 and	
malononitrile	 or	 ethyl	 cyanoacetate	 2	 (1	 mmol)	 in	 water	 (5	
mL),	was	added	SBA‐Pr‐SO3H	(0.02	g)	and	stirred	under	reflux	
condition	 as	 reported	 time	 in	 Table	 1.	 After	 completion	 of	
reaction	(TLC	monitoring),	the	generated	solid	was	dissolved	in	
hot	 ethanol,	 filtered	 for	 removing	 the	 insoluble	 catalyst	 and	
then	 the	 filtrate	 was	 cooled	 to	 afford	 the	 pure	 product	 3a	
(Scheme	1).	

2‐(2‐Oxoindolin‐3‐ylidene)	 malononitrile	 (3a):	 Color:	 Red.	
Yield:	95%.	M.p.:	239‐240	°C.	FT‐IR	(KBr,	ν,	cm‐1):	3358,	3299,	
3134,	2928,	2880,	2195,	1718,	1663,	1609,	1365,	1224,	792.	

2‐(5‐Chloro‐2‐oxoindolin‐3‐ylidene)	 malononitrile	 (3b):	
Color:	Red.	Yield:	90%.	M.p.:	 228‐230	 °C.	 FT‐IR	 (KBr,	 ν,	 cm‐1):	
3571,	3508,	3131,	3064,	2969,	2235,	1729,	1595,	1460,	825.	1H	
NMR	(250	MHz,	CDCl3,	δ,	ppm):	11.36	(s,	1H,	NH),	7.76	(s,	1H,	
ArH),	7.61	(d,	J	=	5.25	Hz,	1H,	ArH),	6.96	(d,	J	=	5	Hz,	1H,	ArH).	
MS	(EI,	m/z	(%)):	229	(M+,	100),	203	(51),	175	(19),	139	(55),	
112	(17),	87	(12).	

2‐(5‐Bromo‐2‐oxoindolin‐3‐ylidene)	 malononitrile	 (3c):	
Color:	Red.	Yield:	93%.	M.p.:	 236‐238	 °C.	 FT‐IR	 (KBr,	 ν,	 cm‐1):	
3580,	3513,	3102,	2851,	2232,	1727,	1619,	1594,	1466,	849.	1H	
NMR	(250	MHz,	CDCl3,	δ,	ppm):	11.36	(s,	1H,	NH),	7.89	(s,	1H,	
ArH),	 7.63	 (d,	 J	 =	 5.25	Hz,	 1H,	 ArH),	 6.92	 (d,	 J	 =	 4.25	Hz,	 1H,	
ArH).	MS	 (EI,	m/z	 (%)):	 273	 (M+,	 20),	 245	 (8),	 167	 (24),	 149	
(100),	139	(32),	112	(16),	71	(32),	57	(61),	43	(58).	

2‐(5‐Nitro‐2‐oxoindolin‐3‐ylidene)	malononitrile	(3d):	Color:	
Red.	 Yield:	 90%.	M.p.:	 262‐264	 °C.	 FT‐IR	 (KBr,	 ν,	 cm‐1):	 3376,	
2972,	2924,	2854,	2199,	1711,	1646,	1614,	1529,	1474,	1076,	
814.	

Ethyl	 2‐(2‐oxoindolin‐3‐ylidene)	 cyano	 acetate	 (3e):	 Color:	
Red.	 Yield:	 90%.	M.p.:	 208‐209	 °C.	 FT‐IR	 (KBr,	 ν,	 cm‐1):	 3446,	
3367,	2923,	2854,	2215,	1727,	1614,	1581,	1462,	1268,	764.	

Ethyl	2‐(5‐chloro‐2‐oxoindolin‐3‐ylidene)	cyano	acetate	(3f):	
Color:	Red.	Yield:	90%.	M.p.:	 225‐227	 °C.	 FT‐IR	 (KBr,	 ν,	 cm‐1):	
3449,	3357,	3283,	3131,	3090,	2980,	2926,	2854,	2213,	1724,	
1612,	 1581,	 1368,	 1250,	 845.	 1H	 NMR	 (250	 MHz,	 CDCl3,	 δ,	
ppm):	8.39	(s,	1H,	NH),	7.52	(d,	J	=	11	Hz,	1H,	ArH),	7.43	(d,	J	=	
8.5	Hz,	1H,	ArH),	6.86	(dd,	J	=	8.50,	7.25	Hz,	1H,	ArH),	4.26	(q,	J	

=	6	Hz,	2H,	CH2),	1.45	(t,	J	=	7.25	Hz,	3H,	CH3).	MS	(EI,	m/z	(%)):	
276	(M+,	100),	231	(38),	204	(80),	176	(59),	148	(40),	114	(19).	

Ethyl	 2‐(5‐bromo‐2‐oxoindolin‐3‐ylidene)	 cyano	 acetate	
(3g):	 Color:	 Red.	 Yield:	 85%.	M.p.:	 225‐227	 °C.	 FT‐IR	 (KBr,	 ν,	
cm‐1):	3448,	3363,	3131,	3093,	2924,	2854,	2213,	1724,	1611,	
1580,	1448,	1250,	764.	1H	NMR	(250	MHz,	CDCl3,	δ,	ppm):	8.54	
(s,	1H,	NH),	7.54	(d,	J	=	1.75	Hz,	1H,	ArH),	7.46	(d,	J	=	5.75	Hz,	
1H,	ArH),	6.77	 (d,	 J	=	8.25	Hz,	1H,	ArH),	4.50	 (q,	 J	=	7	Hz,	2H,	
CH2),	1.45	(t,	J	=	7	Hz,	3H,	CH3).	MS	(EI,	m/z	(%)):	320	(M+,	4),	
279	(8),	167	(12),	149	(78),	97	(20),	81	(48),	69	(88),	57	(100),	
41	(70).	

Ethyl	2‐(5‐nitro‐2‐oxoindolin‐3‐ylidene)	cyano	acetate	 (3h):	
Color:	Red.	Yield:	 85%.	M.p.:	238‐239	 °C.	FT‐IR	 (KBr,	 ν,	 cm‐1):	
3317,	3121,	2929,	2860,	2194,	1730,	1660,	1610,	1474,	1358,	
1217,	862,	758.	
	
3.	Results	and	discussion		

	
In	 this	 manuscript,	 2‐oxoindolin‐3‐ylidene	 malononitrile/	

cyanoacetate	 derivatives	3a‐h	 were	 synthesized	 via	 a	 simple,	
mild	 and	 effective	 reaction	 of	 isatins	 1	 and	 malononitrile	 or	
ethyl	cyanoacetate	2	 in	 the	presence	of	nanoporous	solid	acid	
catalyst	 (SBA‐Pr‐SO3H)	 in	 aqueous	 medium	 (Scheme	 1).	
Considering	 solvent	 effects	 in	 this	 reaction,	 it	was	 found	 that	
water	 is	 the	 solvent	 of	 choice	 which	 results	 in	 high	 product	
yields	 in	 shorter	 reaction	 times	 (Table	 2).	 Four	 substituted	
isatins	 were	 subjected	 to	 this	 reaction	 to	 investigate	 the	
generality	 of	 this	 method	 and	 corresponding	 products	 were	
successfully	synthesized	(Table	1).	It	was	found	that	when	ethyl	
cyanoacetate	was	used,	the	reaction	time	was	longer	than	those	
with	malononitrile.	After	completion	of	the	reaction	(monitored	
by	 TLC),	 the	 crude	 product	was	 dissolved	 in	 hot	 ethanol,	 the	
heterogeneous	solid	catalyst	was	removed	by	simple	filtration,	
and	 after	 cooling	 of	 the	 filtrate,	 the	 pure	 crystals	 of	 products	
were	obtained	as	red	crystals.	

The	most	probable	mechanism	for	this	reaction	is	shown	in	
Scheme	 2.	 Initially,	 the	 solid	 acid	 catalyst	 protonates	 the	
carbonyl	 group	 of	 isatin	 1,	 which	 then	 condenses	 with	 CH‐
acidic	group	of	malononitrile	or	ethyl	cyanoacetate	2	through	a	
fast	Knoevenagel	 condensation	 to	 afford	 the	desired	 products	
3a‐h	(Scheme	2).	



312	 Lashgari	et	al.	/	European	Journal	of	Chemistry	3	(3)	(2012)	310‐313	
	

	

 
	

Scheme	2
	
	

Table	3.	Comparison	of	different	conditions	in	the	synthesis	of	2‐oxoindolin‐3‐ylidene	malononitrile/cyanoacetate	derivatives	3a‐h.	
Entry	 Catalyst	 Solvent Condition* Time	(min) Yield	(%)	 Year	 Ref.
1	 Piperidine	 EtOH Reflux 240 73	 1958	 [12]
2	 ‐	 MeOH Stir.	(r.t.) 15 77	 1972	 [14]
3	 ‐	 EtOH	 Stir.	(r.t.)	 90		 93	 1989	 [13]	
4	 ‐	 DMSO	 Heating	 120	 92	 1989	 [15]	
5	 Neutral	alumina	 ‐	 MW	 5	 78	 1999	 [16]	
6	 Triethanolamine	 EtOH Stir.	(r.t.) 120 70	 2007	 [33]
7	 Tris(2‐hydroxy‐ethyl)amine	 EtOH	 Heating	 60	 90	 2008	 [34]	
8	 Neutral	alumina	 MeOH Stir.	(r.t.) 20 96	 2009	 [4]
9	 DBU	 EtOH Heating 15 88	 2009	 [35]
10	 ‐	 H2O	(1‐5	equiv.) Grinding 15 99	 2011	 [19]
11	 SBA‐Pr‐SO3H	 H2O	 Reflux 5 95	 This	work
*	r.t.:	Room	temperature.	
	

	
	

Figure	1.	SBA‐Pr‐SO3H	acts	as	a	nano‐reactor.
	

	

	
	

Figure	2.	Schematic	illustration	for	the	preparation	of	SBA‐Pr‐SO3H.	
	
	
Literature	surveys	reveal	that	various	conditions	have	been	

employed	 for	 the	 synthesis	 of	 2‐oxoindolin‐3‐ylidene	
malononitrile/cyanoacetate	 derivatives.	 Table	 3	 illustrates	 a	
comparison	of	the	effectiveness	of	various	catalysts	used	in	the	
synthesis	of	these	compounds.	

The	 high	 yields	 of	 reactions	 are	 attributed	 to	 the	 high	
efficiency	 of	 nanopore	 size	 about	 6	 nm	 of	 solid	 acid	 catalyst,	
which	 could	 act	 as	 a	 nano‐reactor	 (Figure	 1).	 A	 schematic	
illustration	 for	 the	 preparation	 of	 SBA‐Pr‐SO3H	was	 shown	 in	
Figure	2.		



Lashgari	et	al.	/	European	Journal	of	Chemistry	3	(3)	(2012)	310‐313	 313	
 

	

	
(a)																																																																																					(b)	

	
Figure	3.	SEM	image	(a)	and	TEM	image	(b)	of	SBA‐Pr‐SO3H.

	
	
First,	the	calcined	SBA‐15	silica	was	functionalized	with	(3‐

mercaptopropyl)	 trimethoxysilane	 (MPTS)	 and	 then,	 the	 thiol	
groups	could	be	completely	oxidized	 into	sulfonic	acid	groups	
by	 hydrogen	 peroxide.	 The	 texture	 properties	 of	 SBA‐15	 and	
SBA‐Pr‐SO3H	such	as	 the	surface	area,	 average	pore	diameter,	
and	 pore	 volume	 have	 been	 measured.	 The	 surface	 of	 the	
catalyst	was	 analyzed	by	different	methods	 such	 as	TGA,	BET	
and	 other	 methods	 which	 were	 confirmed	 that	 the	 organic	
groups	(propyl	sulfonic	acid)	were	immobilized	into	the	pores	
[28].	

Figure	 3	 illustrates	 the	 SEM	 and	 TEM	 images	 of	 SBA‐Pr‐
SO3H.	SEM	image	(Figure	3a)	shows	uniform	particles	about	1	
µm.	The	same	morphology	was	observed	for	SBA‐15.	It	can	be	
concluded	that	morphology	of	solid	was	saved	without	change	
during	 the	 surface	modifications.	On	 the	 other	hand,	 the	TEM	
image	 (Figure	 3b)	 reveals	 the	 parallel	 channels,	 which	
resemble	the	pores	configuration	of	SBA‐15.	This	indicates	that	
the	 pore	 of	 SBA‐Pr‐SO3H	was	 not	 collapsed	 during	 two	 steps	
reactions.	
	
4.	Conclusion	

	
In	 summary	 an	 efficient	 method	 for	 Knoevenagel	

condensation	 of	 isatins	 with	 malononitrile	 or	 ethyl	
cyanoacetate	 in	 the	presence	of	a	 catalytic	 amount	of	 SBA‐Pr‐
SO3H	 in	 aqueous	 medium	 was	 described.	 We	 have	
demonstrated	 that	 sulfonic	 acid	 functionalized	 SBA‐15	 is	 a	
remarkably	efficient	catalyst	for	the	synthesis	of	2‐oxoindolin‐
3‐ylidene	 malononitrile/cyanoacetate	 derivatives	 3a‐h.	 Short	
reaction	times,	excellent	product	yields,	being	environmentally	
benign,	 and	 simple	 workup	 procedure	 are	 the	 advantages	 of	
this	methodology.	
	
Acknowledgements	
	

We	 gratefully	 acknowledge	 for	 financial	 support	 from	 the	
Research	 Council	 of	 Alzahra	 University	 and	 University	 of	
Tehran.	
	
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