Abstract
Treatment of 2-(2-bromoacetyl)-3H-benzo[f]chromen-3-one with pyridine, quinoline, and 2-methylquinoline afforded the corresponding pyridinium, quinolinium and 2-methylquinolinium bromides. The latter salts underwent [3 + 2] 1,3-dipolar cycloaddition with some electron deficient acetylene and ethylene derivatives to give the corresponding indolizine and pyrrolo[1,2-a]quinoline derivatives. Moreover, 2-(2-bromoacetyl)-3H-benzo[f]chromen-3-one reacted with arylidene cyanothioacetamides to afford the corresponding 2-amino-4,5-dihydrothiophene-3-carbonitriles. The synthesised compounds were characterised based on their elemental analysis and spectral data. Antimicrobial activity of some of the synthesised compounds was evaluated.
References
1.
Artico
M.
,
Massa
S.
,
Stefancich
G.
,
Silvestri
R.
,
Di Santo
R.
, and
Corelli
F.
, J. Heterocycl. Chem. , 1989 , 26 , 503 .
2.
Bols
M.
,
Lillelund
V.H.
,
Jensen
H.H.
, and
Liang
X.
, Chem. Rev. , 2002 , 102 , 515 .
3.
Pearson
W.H.
, and
Guo
L.
, Tetrahedron Lett. , 2001 , 42 , 8267 .
4.
Asano
N.
,
Nash
R.J.
,
Molyneux
R.J.
, and
Fleet
G.W.J.
, Tetrahedron: Asymmetry , 2000 , 11 , 1645 .
5.
Kallay
K.R.
, and
Doerge
R.F.
, J. Pharm. Sci. , 1972 , 61 , 949 .
6.
Kitadokoro
K.
,
Hagishita
S.
,
Sato
T.
,
Ohtani
M.
, and
Miki
K.
, J. Biochem. , 1998 , 123 , 619 .
7.
Bolle
L.D.
,
Andrei
G.
,
Snoeck
R.
,
Zhang
Y.
,
Lommel
A.V.
,
Otto
M.
,
Bousseau
A.
,
Roy
C.
,
Clercq
E.D.
, and
Naesens
L.
, Biochem. Pharmacol. , 2004 , 67 , 325 .
8.
Campagna
F.
,
Carotti
A.
,
Casini
G.
, and
Macripo
M.
, Heterocycles , 1990 , 31 , 97 .
9.
Comins
D.L.
, and
Zeller
E.
, Tetrahedron Lett. , 1991 , 42 , 5889 .
10.
Billeret
D.
,
Blondeau
D.
, and
Sliwa
H.
, J. Heterocycl. Chem. , 1993 , 30 , 671 .
11.
Wang
C.J.
,
Hsieh
Y.J.
,
Chu
C.Y.
,
Lin
Y.L.
,
Tseng
T.H.
, Cancer Lett. , 2002 , 83 , 163 .
12.
Gomha
S.M.
, and
Khalil
Kh. D.
, Molecules , 2012 , 17 , 9335 .
13.
Kayser
O.
, and
Kolodziej
H.
, Planta. Med. , 1997 , 63 , 508 .
14.
Olayinka
O.A.
, and
Obinna
C.N.
, J. Heterocycl. Chem. , 2010 , 47 , 179 .
15.
Doucet
C.
,
Pochet
L.
,
Thierry
N.
,
Pirotte
B.
,
Delarge
J.
, and
Reboud-Ravaux
M.
, J. Med. Chem. , 1999 , 42 , 4161 .
16.
Pochet
L.
,
Doucet
C.
,
Schynts
M.
,
Therry
N.
,
Boggetto
N.
,
Pirotte
B.
,
Jiang
K.Y.
,
Masereel
B.
,
de Tullio
P.
,
Delarge
J.
, and
Ravaux
M.R.
, J. Med. Chem. , 1996 , 39 , 2579 .
17.
Cravotto
G.
,
Nano
G.M.
,
Palmisano
G.
, and
Tagliapietra
S.
, Tetrahedron: Asymmetry , 2001 , 12 , 707 .
18.
Dawood
K.M.
, Expert Opin. Therap. Patents , 2013 , 23 , 1133 .
19.
Gomha
S.M.
,
Khalil
Kh. D.
,
El-Zanate
A.M.
, and
Riyadh
S.M.
, Heterocycles , 2013 , 87 , 1109 .
20.
Gomha
S.M.
, and
Abdel-Aziz
H.M.
, J. Chem. Res. , 2013 , 5 , 298 .
21.
Badrey
M.G.
, and
Gomha
S.M.
, Molecules , 2012 , 17 , 11538 .
22.
Gomha
S.M.
, and
Abdel-Aziz
H.A.
, Heterocycles , 2012 , 85 , 2291 .
23.
Gomha
S.M.
, and
Riyadh
S.M.
, Molecules , 2011 , 16 , 8244 .
24.
Gomha
S.M.
, Monatsh. Chem. , 2009 , 140 , 213 .
25.
Moustapha
C.
,
Abdel-Riheem
N.A.
, and
Abdelhamid
A.O.
, Synth. Commun. , 2005 , 35 , 249 .
26.
Kheder
N.A.
,
Darwish
E.S.
, and
Dawood
K.M.
, Heterocycles , 2009 , 78 , 177 .
27.
Katritzky
A.R.
,
Grzeskowiak
N.E.
, and
Alvarez-Builla
J.
, J. Chem. Soc., Perkin Trans. 1 , 1981 , 1180 .
28.
Kesteleyn
B.
,
Puyvelde
L.V.
, and
De Kimpe
N.
, J. Org. Chem. , 1999 , 64 , 438 .
29.
Samet
A.V.
,
Shestopalov
A.M.
,
Nesterov
V.N.
, and
Semenov
V.V.
, Synthesis , 1997 , 623 .
30.
Dawood
K.M.
, Synth. Commun. , 2001 , 31 , 1647 .
31.
Hanedanian
M.
,
Loreau
O.
,
Taran
F.
, and
Mioskowski
C.
, Tetrahedron Lett. , 2004 , 45 , 7035 .
32.
Dawood
K.M.
,
Abdel-Gawad
H.
,
Ellithey
M.
,
Mohamed
H.A.
, and
Hegazi
B.
, Arch. Pharm. Chem. Life Sci. , 2006 , 339 , 133 .
33.
Brunskill
J.S.A.
,
De
A.
, and
Ewing
D.F.
, J. Chem. Soc., Perkin Trans. 1 , 1978 , 629 .
34.
Smania
A.
,
Monache
F.D.
,
Smania
E.F.A.
, and
Cuneo
R.S.
, Int. J. Med. Mushrooms , 1999 , 1 , 325 .