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European	Journal	of	Chemistry	8	(1)	(2017)	42‐45	

	

European	Journal	of	Chemistry	
ISSN	2153‐2249	(Print)	/	ISSN	2153‐2257	(Online)		2017	Atlanta	Publishing	House	LLC	‐	All	rights	reserved	‐	Printed	in	the	USA	

http://dx.doi.org/10.5155/eurjchem.8.1.42-45.1519 

	
	

	

	

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

	 	 	

One	pot	synthesis	of	substituted	1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐one	
derivatives	

Yellanki	Jagannadham	1,2,	Bhoomireddy	Ramadevi	2	and	Bethanamudi	Prasanna	1,2,*	

1	Research	Center,	Department	of	Chemistry,	Chaitanya	Post	Graduate	College	(Autonomous),	Hanamkonda,	Warangal,	506001,	India	
2	College	of	Engineering,	Jawaharlal	Nehru	Technological	University,	Hyderabad,	500085,	India	

*	Corresponding	author	at:	Research	Center,	Department	of	Chemistry,	Chaitanya	Post	Graduate	College	(Autonomous),	Hanamkonda,	Warangal,	506001,	India.		
Tel.:	+91.986.6825885.	Fax:	+91.986.6825885.	E‐mail	address:	prasschem@gmail.com	(B.	Prasanna).	

	
	

	 	

	 	 	

ARTICLE	INFORMATION	 	 ABSTRACT	

	
DOI: 10.5155/eurjchem.8.1.42-45.1519	

Received:	15	December	2016	
Received	in	revised	form:	19	January	2017	
Accepted:	21	January	2017	
Published	online:	31	March	2017	
Printed:	31	March	2017

 

	 The	 title	 compounds,	 substituted	 1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones	 were
obtained	 by	 reacting	 3‐aryl‐1‐(3‐coumarinyl)propen‐1‐ones	 with	 2‐napthol	 catalyzed	 by
DBU	 (1,8‐diazabicyclo[5,4,0]undec‐7‐ene)	 and	 concentrated	 H2SO4	 in	 ample	 yields.	 Their
structures	were	characterized	by	IR,	1H	NMR,	13C	NMR,	mass	spectral	and	elemental	analysis.
All	 the	 synthesized	 compounds	have	 been	 evaluated	 for	 their	 in‐vitro	antibacterial	 activity
against	Escherichia	coli,	Staphylococcus	aureus,	and	Pseudomonas	aeruginosa	and	antifungal
activity	against	Aspergillus	Niger	and	Candida	albicans	by	using	serial	broth	dilution	method.
Among	those	compounds	3	band	3c	exhibits	prominent	results.	

KEYWORDS	
DBU	
Coumarins	
Sulfuric	acid	
Cinnamoyl	chromens	
Antimicrobial	activity	
Hydroxyl	naphthalene	

Cite	this: Eur.	J.	Chem.	2017,	8(1),	42‐45

	
1.	Introduction	
	

Chromene	derivatives	 are	known	 to	 exhibit	 a	wide	 range	
of	 biological	 activities,	 such	 as	 antifungal,	 antibacterial	 [1‐5],	
antioxidative	 [6],	 antileishmanial	 [7],	 antitumor	 [8,9],	 hypo‐
tensive	 [9],	 antiproliferation	 [10,11],	 local	 anesthetic	 [12],	
antiallergenic	 [13,14],	 central	 nervous	 system	 activities	 and	
effects	 [15],	 as	 well	 as	 efficacious	 in	 the	 treatment	 of	
Alzheimer’s	 disease	 [16]	 and	 schizophrenia	 disorder	 [17].	
Coumarins	 are	 of	 scientific	 interest	 as	 anti‐HIV	 agents	 [18],	
antituberculosis	 agents	 [19],	 cholinesterase	 and	 monoamine	
oxidase	 inhibitors	 [20],	 antioxidants	 and	 anti‐inflammatory	
[21,22].	

In	 continuation	of	our	work	on	 the	 synthesis	of	 tetrazolo	
and	 triazolo	 pyrimidin‐yl‐2H‐chromen‐2‐ones	 [23],	 we	 have	
developed	 a	 new	 route	 to	 synthesis	 of	 substituted	 1H‐benzo	
[f]chromen‐3‐yl‐2H‐chromen‐2‐ones	 from	 3‐aryl‐1‐(3‐couma‐
rinyl)propen‐1‐ones	 with	 2‐napthol	 catalyzed	 by	 1,8‐diaza	
bicyclo[5,4,0]undec‐7‐ene	 (DBU)	 and	 concentrated	 H2SO4	 in	
high	yields	and	also	studied	their	antimicrobial	activity.	
	
2.	Experimental	
	
2.1.	Instrumentations	

Melting	points	were	 recorded	 in	open	 capillary	 and	were	
uncorrected.	 Column	 chromatography	 was	 performed	 using	
silicagel	 (100‐200	mesh	 size)	 purchased	 from	Thomas	Baker	
and	 TLC	 was	 carried	 out	 using	 aluminum	 sheets	 pre‐coated	
with	silica	gel	60F254	purchased	from	Merck.	 IR	spectra	(KBr)	
were	 recorded	 on	 a	 Bruker	 WM‐4(X)	 spectrometer	 (577	
model).	 1H	 NMR	 (300	MHz)	 and	 13C	 NMR	 (75	MHz)	 spectra	
were	 recorded	 on	 Bruker	 AC‐300	 spectrometer	 in	 DMSO‐ 6	

with	 TMS	 as	 an	 internal	 standard.	 Mass	 spectra	 (ESI)	 were	
recorded	 on	 JEOL	 SX‐102	 spectrometer.	 CHN	 analysis	 was	
done	by	Carlo	Erba	EA	1108	automatic	elemental	analyzer.		
	
2.2.	Materials	
	

The	 chemicals	 and	 solvents	 used	 were	 of	 commercial	
grade	 and	 were	 used	 without	 further	 purification	 unless,	
otherwise,	stated.	
	
2.3.	Synthesis	
	
2.3.1.	Synthesis	of	substituted‐1H‐benzo[f]chromen‐3‐yl‐2H‐
chromen‐2‐ones	(3a‐e)	
	

	



Jagannadham	et	al.	/	European	Journal	of	Chemistry	8	(1)	(2017)	42‐45	 43	
 

	

O O

O

+

OH

O

OO

R

R

DBU

H2SO4

1a-e
2 3a-e

R = a) -C6H4-Cl; b) -C6H4-OMe; c)-C6H3-Cl2; d) -C6H4-OH; e) -C5H4N
 

Scheme	1
	
	
To	 a	 stirred	 solution	 of	 compound	1a‐e	 (0.12	mmol),	 2‐

naphthol	 (2)	 (0.12	mmol)	 and	DBU	 (0.02	mmol)	 in	DCM	(2.0	
mL)	was	 reacted	 at	 room	 temperature	 for	 12	 h,	 the	 reaction	
was	monitored	by	TLC.	Then	a	drop	of	concentrated	H2SO4	was	
added	 directly	 and	 stirring	 was	 continued	 for	 3	 h	 at	 room	
temperature.	 The	 crude	 reaction	 mixture	 was	 purified	 by	
column	chromatography	by	using	ethyl	acetate	and	petroleum	
ether	(1:9,	v:v)	to	give	the	corresponding	products	(Scheme	1).	

3‐(1‐(2‐Chlorophenyl)‐	 1H‐benzo[f]chromen‐3‐yl)‐2H‐chro	
men‐2‐one	 (3a):	 Color:	 White.	 Yield:	 78%.	 M.p.:	 172‐173	 °C.	
FT‐IR	(KBr,	,	cm‐1):	1742	(CO),	1645	(cyclic	CO),	1592	(C=C),	
1056	(C‐Cl).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	4.84	(d,	1H,	
CH),	5.78	(d,	1H,	CH),	7.19‐7.26	(m,3H,	Ar‐H),	7.48‐7.50	(d,	2H,	
Ar‐H),	 7.54‐7.58	 (m,	 3H,	 Ar‐H),	 7.72‐7.74	 (d,	 2H,Ar‐H),	 7.80‐
7.84	 (m,	 2H,	 Ar‐H),	 8.14‐8.18	 (m,	 2H,	 Ar‐H),	 8.52	 (s,	 1H,	
coumarin‐H).	13C	NMR	(75	MHz,	DMSO‐d6,	δ,	ppm):	38.4	(1C,	C‐
4’),	98.4	(1C,	C‐3’),	117.4	(1C,	C‐8),	119.3	(1C,	C‐9),	119.8	(1C,	
C‐7’),	123.4	(1C,	C‐10’),124.5	(1C,	C‐5’),	125.1	(1C,	C‐6),	125.9	
(1C,	 C‐4),	 127.2	 (1C,	 C‐7),	 127.6	 (1C,	 C‐4’’),	 128.0	 (1C,	 C‐6’’),	
128.7(1C,	 C‐12’),	 129.1	 (1C,	 C‐11’),	 129.5	 (1C,	 C‐5),	 129.9(1C,	
C‐9’),	 130.4	 (1C,	 C‐13’),	 130.9	 (1C,	 C‐5’’),	 131.4	 (1C,	 C‐14’),	
132.0	(1C,	C‐8’),	132.4	(1C,	C‐7),	133.8	(1C,	C‐3),	150.3	(1C,	C‐
1’’),	150.8	(1C,	C‐6’),	151.8	(1C,	C‐10),	157.4	(1C,	‐O‐C‐2’),	159.5	
(1C,	 CO),	 160.4	 (1C,	 C‐3’’).	 MS	 (EI,	 m/z):	 437	 (M+1)+.	 Anal.	
calcd.	 for	 C28H17ClO3:	 C,	 76.98;	 H,	 3.92.	 Found:	 C,	 76.92;	 H,	
3.89%.	

3‐(1‐(3‐Methoxyphenyl)‐	1H‐benzo[f]chromen‐3‐yl)‐2H‐chro	
men‐2‐one	 (3b):	 Color:	 White.	 Yield:	 69%.	 M.p.:	 201‐203	 °C.	
FT‐IR	(KBr,	,	 cm‐1):	1746	(CO),	1648	(cyclic	CO),1590	(C=C).	
1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	3.84	(s,	3H,	OCH3),	5.10	
(d,	1H,	CH),	6.19	(d,	1H,	CH),	6.67‐6.76	(m,3H,	Ar‐H),	7.02‐7.05	
(d,	4H,	Ar‐H),	7.41‐7.50	(m,	3H,	Ar‐H),	7.69‐7.76	(m,	2H,	Ar‐H),	
7.92‐7.94	(d,	2H,	Ar‐H),	8.63	(s,	1H,	coumarin‐H).	13C	NMR	(75	
MHz,	DMSO‐d6,	δ,	ppm):	42.4	(1C,	OCH3,	C‐7’’),	56.2	 (1C,	C‐4’),	
96.2	(1C,	C‐3’),	113.4	(1C,	C‐4’),	114.2	(1C,	C‐2’),	117.2	(1C,	C‐
9),	120.4	(1C,	C‐5),	121.2	(1C,	C‐6’’),	121.7	(1C,	C‐5’),	123.5	(1C,	
C‐12’),	124.3	(1C,	C‐10’),	124.9	(1C,	C‐7),	126.2	(1C,	C‐6),	126.9	
(1C,	 C‐4),	 127.5	 (1C,	 C‐9’),	 128.4	 (1C,	 C‐8’),	 129.8	 (1C,	 C‐11’),	
130.2	(1C,	C‐3),	131.3	(1C,	C‐5’’),	131.9	(1C,	C‐14’),	132.4	 (1C,	
C‐13’),	144.6	(1C,	C‐1’),	152.4	(1C,	C‐6’),	152.9	(1C,	C‐10),	157.2	
(1C,	C‐2’),	167.2	(1C,	‐CO,	C‐2),	171.4	(1C,	‐C‐CH3,	C‐3’’).	MS	(EI,	
m/z):	 433	 (M+1)+.	Anal.	 calcd.	 for	C29H20O4:	C,	80.54;	H,	4.66.	
Found:	C,	80.48;	H,	4.63%.	

3‐(1‐(2,	 3‐Dichlorophenyl)‐1H‐benzo[f]chromen‐3‐yl)‐2H‐
chromen‐2‐one	(3c):	Color:	Grey.	Yield:	65%.	M.p.:	186‐187	°C.	
FT‐IR	(KBr,	,	cm‐1):	1742	(CO),	1652	(cyclic	CO),	1585	(C=C).	
1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	5.76	(s,	1H,	CH),	6.73	(d,	
1H,	CH),	7.15‐7.28	(m,	2H,	Ar‐H),	7.34‐7.39	(m,	3H,	Ar‐H),	7.43‐
7.53	(m,	3H,	Ar‐H),	7.57‐7.63	(m,	3H,	Ar‐H),	7.96‐8.00	(d,	2H,	
Ar‐H),	8.58	(s,	1H,	coumarin‐H).	13C	NMR	(75	MHz,	DMSO‐d6,	δ,	
ppm):	41.4	(1C,	C‐4’),	98.4	(1C,	C‐3’),	117.5	(1C,	C‐8),	119.2	(1C,	
C‐9),	 119.9	 (1C,	 C‐7’),	 124.6,	 (1C,	 C‐10’),	 125.3	 (1C,	 C‐12’),	
125.9	(1C,	C‐11’),	126.8	(1C,	C‐6’’),	127.6	(1C,	C‐4’’),	128.2	(1C,	
C‐5’’),	128.7	(1C,	C‐9’),	129.3	(1C,	C‐5),	129.9	(1C,	C‐14’),	130.4	
(1C,	 C‐2’),	 130.9	 (1C,	 C‐3),	 131.8	 (1C,	 C‐3’),	 132.0	 (1C,	 C‐13’),	
132.4	(1C,	C‐3’),	135.2	(1C,	C‐13’’),	153.2	(1C,	C‐2’),	154.3	(1C,	

C‐1’),	157.9	(1C,	C‐10),	160.7	(1C,	‐O‐C‐2’),	162.8	(1C,‐OC,‐C‐2).	
MS	(EI,	m/z):	472	(M+1)+.	Anal.	calcd.	for	C28H16Cl2O3:	C,	71.35;	
H,	3.42.	Found:	C,	71.32;	H,	3.39%.	

3‐(1‐(2‐Hydroxyphenyl)‐1H‐benzo[f]chromen‐3‐yl)‐2H‐chro	
men‐2‐one	(3d):	Color:	Brown.	Yields:	71%.	M.p.:	197‐199	°C.	
FT‐IR	(KBr,	,	cm‐1):	1740	(CO),	1657	(cyclic	CO),	1585	(C=C),	
3345(OH).	1H	NMR	(300	MHz,	DMSO‐d6,	δ,	ppm):	4.82	(d,	1H,	
CH),	 5.48	 (s,	 1H,	 CH),	 6.92‐7.08	 (m,	 2H,	 Ar‐H),	 7.09‐7.10	 (m,	
2H,	 Ar‐H),	 7.35‐7.39	 (m,	 4H,	 Ar‐H),	 7.65‐7.67	 (m,	 2H,	 Ar‐H),	
7.73‐7.75	 (m,	2H,	Ar‐H),	8.20‐8.32	 (m,	2H,	Ar‐H),	8.61	 (s,	1H,	
coumarin‐H),	9.71	(br,	1H,	OH).	13C	NMR	(75	MHz,	DMSO‐d6,	δ,	
ppm):	42.2	(1C,	C‐4’),	98.4	(1C,	C‐3’),	117.7	(1C,	C‐8),	119.9	(1C,	
C‐9),	119.9	(1C,	C‐7’),	120.4	(1C,	C‐3’’),	124.3	(1C,	C‐1’’),	124.6	
(1C,	C‐5’),	124.8	(1C,	C‐12’),	125.9	(1C,	C‐10’),	126.8	(1C,	C‐11’),	
127.3	(1C,	C‐4),	128.4	(1C,	C‐9’),	128.7	(1C,	C‐4’’),	129.2	(1C,	C‐
6),	129.8	(1C,	C‐8’),	129.9	(1C,	C‐5),	130.6	(1C,	C‐7),	130.9	(1C,	
C‐14’),	131.0	(1C,	C‐6’),	132.4	(1C,	C‐13’),	135.2	(1C,	C‐3),	153.4	
(1C,	C‐10),	154.3	(1C,	C‐6’),	157.9	(1C,	‐C‐OH,	C‐2’),	161.4	(1C,	‐
O‐C‐2’),	 162.5	 (1C,	 CO,	 ‐C‐2).	MS	 (EI,	m/z):	 419	 (M+1)+.	Anal.	
calcd.	for	C28H18O4:	C,	80.37;	H,	4.34.	Found:	C,	80.30;	H,	4.32%.	

3‐(1‐(Pyridine‐2‐yl)‐1H‐benzo[f]chromen‐3‐yl)‐2H‐chromen	
‐2‐one	 (3e):	 Color:	 Grey.	 Yield:	 58%.	M.p.:	 161‐163	 °C.	 FT‐IR	
(KBr,	 ,	 cm‐1):	 1744	 (CO),	 1652	 (cyclic	 CO),	 1588	 (C=C).	 1H	
NMR	 (300	MHz,	DMSO‐d6,	 δ,	 ppm):	 4.92	 (d,	 1H,	 CH),	 5.82	 (s,	
1H,	CH),	6.96‐7.04	(d,	2H,	Ar‐H),	7.10‐7.14	(d,	2H,	Ar‐H),	7.37‐
7.42	(m,	4H,	Ar‐H),	7.58‐7.62	(m,	2H,	Ar‐H),	7.73‐7.76	(m,	2H,	
Ar‐H),	 8.20‐8.27	 (d,	 2H,	 Ar‐H),	 8.68	 (s,	 1H,	 coumarin‐H).	 13C	
NMR	(75	MHz,	DMSO‐d6,	δ,	ppm):	41.2	(1C,	C‐4’),	98.4	(1C,	C‐
3’),	118.1	(1C,	C‐8),	119.4	(1C,	C‐7’),	119.8	(1C,	C‐9),	121.4	(1C,	
C‐5’’),	 121.5	 (1C,	 C‐5’’),	 123.2	 (1C,	 C‐10’),	 124.2	 (1C,	 C‐12’),	
124.6	(1C,	C‐6),	126.8	(1C,	C‐4),	127.4	(1C,	C‐5),	128.9	(1C,	C‐
3’’),	129.0	(1C,	C‐7),	129.4	(1C,	C‐14’),	129.9	(1C,	C‐11’’),	130.4	
(1C,	 C‐8’),	 131.6	 (1C,	 C‐13’),	 132.5	 (1C,	 C‐9’),	 134.5	 (1C,	 C‐3),	
135.2	(1C,	C‐4’’),	149.6	(1C,	C‐6’’),	154.2	(1C,	C‐6’),	154.8	(1C,	C‐
10),	 156.4	 (1C,	 ‐O‐C‐2’),	 160.2	 (1C,	 C‐2’’),	 164.2	 (1C,	 CO,	C‐2).	
MS	(EI,	m/z):	404	(M+1)+.	Anal.	calcd.	for	C27H17NO3:	C,	80.38;	
H,	4.25,	N,	3.47.	Found:	C,	80.30;	H,	4.21,	N,	3.45%.	
	
2.4.	Antibacterial	activity	
	

The	 antibacterial	 susceptibility	 test	 was	 done	 by	 deter‐
mining	 the	 zone	 of	 inhibition	 by	 using	 disc	 diffusion	method	
[24].	 The	 substituted	 1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐
2‐ones	 (3a‐e)	was	 dissolved	 in	 dimethyl	 sulfoxide	 solvent	 to	
make	a	solution	of	120	µM/mL.	From	this	stock	solution,	serial	
dilutions	have	 been	done	 to	20,	 10,	 5,	 and	 1.25	 µM/mL	with	
dimethyl	 sulfoxide	 in	 sterile	 test	 tubes.	 Sterilized	 filter	 discs	
were	 dipped	 in	 these	 solutions	 and	 subsequently	 dried	 to	
remove	 the	 dimethyl	 sulfoxide.	 Nutrient	 agar	medium	 plates	
were	prepared	using	Muller‐Hinton	agar	and	were	allowed	to	
solidify.	 The	 three	 different	 bacteria	 like	E.	 coli,	 S.	 aureus,	 P.	
aeruginosa	 were	 selected,	 and	 1	 mL	 of	 each	 bacteria	 and	
culture	broth	were	added	to	the	plate	and	spread	with	the	help	
of	a	sterile	spreader.		

	
	



44	 Jagannadham	et	al.	/	European	Journal	of	Chemistry	8	(1)	(2017)	42‐45	
	

	
Table	1.	Zone	of	inhibition	in	mm	of	1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones,	(3a‐e).	
Compound	 3a	 3b	 3c	 3d	 3e	
Escherichia	coli	 10 14 16 10	 08
Staphylococcus	aureus	 12 16 15 08	 10
Pseudomonas	aeruginosa	 08	 15	 14	 08	 10	
Norfloxacin	standard	drug	 14	 14	 14	 14	 14	

	
Table	2.	MIC	of	1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones,	(3a‐e).	
Compound	 3a 3b 3c 3d	 3e
Escherichia	coli	 17 08 10 19	 15
Staphylococcus	aureus	 19 08 06 16	 17
Pseudomonas	aeruginosa	 20 09 08 22	 19
Norfloxacin	standard	drug	 14 14 14 14	 14

	
Table	3.	Zone	of	inhibition	in	mm	of	1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones	(3a‐e)	against	fungi.	
Compound	 3a 3b 3c 3d 3e	
A.	niger	 09	 18	 14	 10	 08	
C.	albicans	 08	 20	 15	 08	 10	
Fluconazole	standard	drug	 16 16 16 16 16	

	
Table	4.	MIC	of	1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones	(3a‐e)	against	fungi.	
Compound	 3a 3b 3c 3d 3e	
A.	niger	 18 08 10 22 20	
C.	albicans	 20 10 09 20 18	
Fluconazole	standard	drug	 12 12 12 12 12	
	

	
The	 filter	 paper	 discs	 soaked	 in	 solution	 of	 1H‐

benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones	 (3a‐e)	 derivatives	
were	placed	aseptically	over	the	inoculated	plates	using	sterile	
forceps.	 The	 plates	 were	 incubated	 at	 37	 °C	 for	 24	 h	 with	
respect	 to	 standard	 drug	 Norfloxacin.	 The	 zone	 of	 inhibition	
was	measured.	
	
2.5.	Antifungal	activity	
	

The	 antifungal	 susceptibility	 test	was	 done	 by	 using	 disc	
diffusion	 method.	 PDA	 (Potato	 Dextrose	 Agar)	 plates	 were	
prepared	 and	 the	 standardized	 suspension	 of	 fungal	 spores	
was	 poured	 and	 uniformly	 spread.	 All	 the	 synthesized	
compounds	 1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones	
(3a‐e)	 were	 dissolved	 in	 dimethyl	 sulfoxide	 to	 make	 a	
concentration	of	 120	µM/mL	and	 serially	diluted	 to	different	
concentrations	of	20,	10,	and	5	µM/mL.	Sterile	discs	with	150	
mm	 diameter	 were	 further	 sterilized	 and	 loaded	 with	
synthesized	 compounds	 and	 after	 drying	 these	 discs	 were	
stored	at	4	°C.	The	fungi	strains	such	as	C.	albicans	and	A.	niger	
was	 incubated	 in	 PDA	 (Potato	 Dextrose	 Agar)	 at	 25	 °C	 for	 5	
days	with	 respect	 to	 standard	drug	Fluconozole.	 The	 zone	of	
inhibition	was	measured.		
	
3.	Results	and	discussion	
	
3.1.	Chemistry	
	

To	develop	a	new	method	for	the	synthesis	of	substituted	
1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐ones	 (3a‐e),	 experi‐
ments	 were	 conducted	 by	 reacting	 3‐aryl‐1‐(3‐coumarinyl)	
propen‐1‐ones(1a‐e)	with	2‐napthol	(2)	catalyzed	by	DBU	and	
concentrated	 H2SO4	 for	 5	 h	 in	 ample	 yields	 (Scheme	 1).	 The	
new	molecules	 (3a‐e)	were	 confirmed	 on	 the	 basis	 of	 IR,	 1H	
NMR,	13C	NMR,	mass	spectral	data,	and	elemental	analysis.		

	
3.2.	Antibacterial	activity	
	

The	antibacterial	activity	of	1H‐benzo[f]chromen‐3‐yl‐2H‐
chromen‐2‐ones	 (3a‐e)	 were	 tested	 on	 bacterial	 resistant’s	
like	Escherichia	 coli,	Staphylococcus	aureus,	 and	Pseudomonas	
aeruginosa	 by	 micro	 dilution	 broth	 method.	 The	 results	 are	
tabulated	 in	 Table	 1	 and	 2.	 The	 zone	 of	 inhibition	 of	Norflo‐
xacin	was	 14	mm	while	 the	 synthesized	molecule	3b	 and	3c	
shown	 14‐16	 mm	 against	 Escherichia	 coli,	 Staphylococcus	
aureus	 and	 Pseudomonas	 aeruginosa.	 Derivatives	 of	 1H‐

benzo[f]chromen‐3‐yl‐2H‐chromen‐2‐one	 (3a‐e)	 exhibited	
prominent	 results.	 The	 most	 encouraging	 results	 were	
obtained	in	the	case	of	compound	3b	and	3chaving	MIC	value	
8‐10	 µM/mL	 against	 Escherichia	 coli,	 Staphylococcus	 aureus	
and	 Pseudomonas	 aeruginosa,	 while	 norfloxacin	 as	 standard,	
shows	MIC	of	14	µM/mL.	
	
3.3.	Antifungal	activity	
	

Antifungal	 activity	 of	 synthesized1H‐benzo[f]chromen‐3‐
yl‐2H‐chromen‐2‐ones	(3a‐e)	tested	against	fungi	like	Candida	
albicans	and	Aspergillus	niger	using	Fluconazole	as	a	standard	
drug.	 All	 the	 synthesized	 compounds	 3a‐e	 shows	 admirable	
antifungal	 results	 against	 Fluconazole	 as	 a	 standard	 drug.	
Among	these,	compounds	3b	and	3c	shows	most	encouraging	
results	 against	A.	niger	 and	C.	albicans.	The	 result	 of	 zone	 of	
inhibition	 of	 Fluconazole	 was	 16	 mm	 while	 the	 synthesized	
molecules	 3b	 and	 3c	 exhibits	 18‐20	 mm.	 The	 results	 are	
shown	in	Table	3	and	4.	
	
4.	Conclusions	
	

Using	 a	 concise	 synthetic	 method,	 we	 successfully	
designed	 substituted	 1H‐benzo[f]chromen‐3‐yl‐2H‐chromen‐
2‐ones	 (3a‐e)	 scaffolds	 and	 obtained	 by	 treating	 3‐aryl‐1‐(3‐
coumarinyl)propen‐1‐ones	with	 2‐napthol	 in	 the	 presence	 of	
DBU	as	catalyst	and	concentrated	H2SO4in	ample	yields.	All	the	
synthesized	compounds	have	been	evaluated	for	their	in	vitro	
antibacterial	 activity	 against	 Escherichia	 coli,	 Staphylococcus	
aureus,	 and	 Pseudomonas	 aeruginosa	 and	 antifungal	 activity	
against	 Aspergillus	 niger	 and	 Candida	 albicans,	 among	 those	
compounds	3b	and	3c	exhibits	prominent	results.	
	
Acknowledgements	
	

The	authors	are	thankful	to	the	Chairman,	Dr.	Chintalapani	
Venkata	 Purushottam	 Reddy,	 Chaitanya	 Colleges	 (Autono‐
mous),	 Hanamakonda,	 Warangal,	 for	 providing	 research	
facilities	and	financial	support.		
	
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