J Chem Crystallogr (2011) 41:449–452
DOI 10.1007/s10870-010-9899-z
ORIGINAL PAPER
Synthesis and Crystal Structure of 1,3-disubstituted-2-propyleno-
1-one Containing Pyrazole Moiety
•
Y.-L. Zhou X.-L. Wu Fang-Ming Liu
•
Received: 19 January 2010 / Accepted: 17 November 2010 / Published online: 8 December 2010
Ó Springer Science+Business Media, LLC 2010
Abstract A series of novel 1,3-disubstituted-2-propyleno-
1-one derivatives containing pyrazole ring were synthesized
and characterized by IR, MS, H1NMR and elemental anal-
ysis. The structure of C25H20N2O2 (3a) was determined by
single crystal X-ray crystallography. C25H20N2O2 is mono-
are joined by a three-carbon a,b-unsaturated carbonyl
system. Chalcone derivatives, especially some heterocyclic
containing chalcones, have been reported to possess
many biological activities, such as anti-inflammatory, anti-
microbial, anti-fungal, anti-oxidant, anti-cancer, anti-tumor
and cytotoxic activities [2–4]. In addition, literature cites
many reports on valuable biological activity of various
pyrazole derivatives [5–8]. Keeping these observations in
mind and in continuation of our studies on the synthesis of
biologically active heterocyclic compounds [9, 10], we
report herein the synthesis of chalcones containing pyra-
zole moiety, which might have useful biological and
therapeutic activities.
clinic with space group P21/c and cell constans: a =
3
˚
˚
˚
˚
9.863(2)A, b = 20.054(4)A, c = 10.274(2)A V = 2028.0(7)A
and Z = 4. In addition, the crystal structure was solved by
direct methods and refined by full-matrix least-squares on F2
to final values of R1 = 0.0657 and wR2 = 0.1806, and it
shows that the complex units are linked by non-classical
hydrogen-bonding. The molecule adopts a trans configura-
tion about the central C = C double bond. The crystal
structure is stabilized by C–OÁÁÁp intermolecular hydrogen
bonds and p–p stacking interactions.
Experimental
Keywords Chalcone Á X-ray Structure Á Pyrazole Á
All chemical reagents were obtained from a commercial
source and used without further purification. Melting points
were recorded on a X-5 micro melting point apparatus and
temperature were uncorrected. The IR spectra were recor-
ded from KBr on a Bruker Tensor 27 spectrophotometer.
MS were recorded on an Agilent 5975 mass selective
detector. X-ray diffraction data were obtained on a Hitachi
F-4500 R-AXIS SPDER diffractometer. Element analyses
were performed on a Perkin-Elmer 240 CHN analyzer.
The synthesis of the target compounds were carried out
as shown in Scheme 1. 1-phenyl-3-methyl-5-phenyloxyl-
4-pyrazolocarbaldehyde 1 was prepared by literature reported
methods [11]. This compound was obtained as dark yellow
crystals. Yield(%): 85; M.p.: 94–95°. General procedure
for synthesis of 1-(4-substituted-phenyl)-3-(1-phenyl-
3-methyl-5-phenyloxyl -pyrazolo-4-yl)-2-propyleno-1-one 3.
To a solution of 1-phenyl-3-methyl-5-phenyloxyl-4-pyr-
azolocarbaldehyde (10 mmol) and 4-substituted acetophenone
Hydrogen Bonds
Introduction
Chalcones, as one of the important classes of natural
product, have been recently subjects of great interest for it
pharmacological activities [1]. Chemically they consist of
open-chain flavonoids in which the two aromatic rings
Y.-L. Zhou Á F.-M. Liu (&)
College of Materials and Chemical Engineering,
Hangzhou Normal University, 310036 Hangzhou,
People’s Republic of China
e-mail: fangmingliu895@yahoo.com.cn
X.-L. Wu Á F.-M. Liu
College of Chemistry and Chemical Engineering, Xinjiang
University, 830046 Urumqi, People’s Republic of China
123
Zhou
