Efficient one-pot synthesis of β-unsaturated isoxazol-5-ones and pyrazol-5-ones under ultrasonic irradiation

Article abstract of DOI:10.1080/00397911.2010.535949

4-Arylmethylidene-3-isopropylisoxazol-5-ones and 4-arylmethylidene-1- phenyl- 3-isopropylpyrazol-5-ones have been prepared from the reactions of hydroxylamine and phenylhydrazine with methyl 4-methyl-3-oxovalerate and aromatic aldehydes in an aqueous medium at room temperature in the presence of pyridine under ultrasonic irradiation. The simple and facile method produced products in good yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/00397911.2010.535949

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Efficient One-Pot Synthesis of β-
Unsaturated Isoxazol-5-ones and
Pyrazol-5-ones Under Ultrasonic
Irradiation
Keyume Ablajan a & Hainimu Xiamuxi a
a College of Chemistry and Chemical Enginnering , Xinjiang
University , Urumqi , China
Accepted author version posted online: 07 Oct 2011.Published
online: 22 Dec 2011.
To cite this article: Keyume Ablajan & Hainimu Xiamuxi (2012) Efficient One-Pot Synthesis
of β-Unsaturated Isoxazol-5-ones and Pyrazol-5-ones Under Ultrasonic Irradiation, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry,
42:8, 1128-1136, DOI: 10.1080/00397911.2010.535949
To link to this article: http://dx.doi.org/10.1080/00397911.2010.535949
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Synthetic Communications1, 42: 1128–1136, 2012
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2010.535949
EFFICIENT ONE-POT SYNTHESIS OF
b-UNSATURATED ISOXAZOL-5-ONES AND
PYRAZOL-5-ONES UNDER ULTRASONIC IRRADIATION
Keyume Ablajan and Hainimu Xiamuxi
College of Chemistry and Chemical Enginnering, Xinjiang University,
Urumqi, China
GRAPHICAL ABSTRACT
Abstract 4-Arylmethylidene-3-isopropylisoxazol-5-ones and 4-arylmethylidene-1-phenyl-
3-isopropylpyrazol-5-ones have been prepared from the reactions of hydroxylamine and
phenylhydrazine with methyl 4-methyl-3-oxovalerate and aromatic aldehydes in an aqueous
medium at room temperature in the presence of pyridine under ultrasonic irradiation. The
simple and facile method produced products in good yields.
Supplemental materials are available for this article. Go to the publisher’s online edition
of Synthetic Communications1 to view the free supplemental file.
Keywords Isoxazol-5-one; 4-methyl-3-oxovalerate; one-pot synthesis; pyrazol-5-one;
three-component reaction
INTRODUCTION
Isoxazolone as an important class of heterocyclic compounds are of both bio-
logical and chemical interest. Some isoxazole derivatives have shown a wide range of
biological activities including antitumor, anti-HIV, cytotoxic, anti-inflammatory,
and anticonvulsant activities.[1–4] Recent studies reveal some isoxazoles derivatives
are potent dual inhibitors.[5] Pyrazole derivatives have a broad spectrum of biologi-
cal activities such as antibacterial, antifungal, and anti-inflammatory activities.[6–9]
A
new pyrazolone derivative is being used as a drug in clinical practice for treatment of
brain ischemia and myocardial ischemia.[10,11] Some of the pyrazolone derivatives
were also found to have varying efficiency in the treatment of HIV and AIDS.[12]
Recently, a series of androgen antagonists with isoxazolone or pyrazolone moiety
Received August 16, 2010.
Address correspondence to Keyume Ablajan, College of Chemistry and Chemical Engineering,
Xinjiang University, 830046 Urumqi, China. E-mail: ablajan209@hotmail.com
1128

ISOXAZOL-5-ONES AND PYRAZOL-5-ONES
1129
Scheme 1. Synthesis of 4-arylmethylidene-3-isopropylisoxazol-5-one (4).
Scheme 2. Synthesis of 4-arylmethylidene-1-phenyl-3-isopropylpyrazol-5-one (6).
were synthesized, and some of them exhibited full antagonistic activity toward
human prostate tumor LNCaP cells.[13,14] The isoxazole derivatives containing iso-
propyl groups exhibited various biological activities,[15] and the pharmacological
activities of heterocycle compounds were significantly affected by the alkyl group
in the heterocyclic ring.[16] Hence, the synthesis of isoaxazolone and pyrazolone deri-
vatives received considerable attention because of their importance in drug industry.
Green methods used in synthetic chemistry have attracted much attention for
their easy operation, environmental friendliness, and economical manipula-
tions.[17,18] Multicomponent reactions (MCRs) have become widely used in organic
synthesis and combinatorial chemistry because of their straightforward reactions,
simple experimentation, and high yields of the products.[19–21] The most evident
improvement for the synthesis of target compounds by using MCRs are in the
reduction of reaction time, use of green solvent, and fewer side products. If the reac-
tion could be carried out in water, it would be the most green method and more
advantageous economically and environmentally.[22–24] Ultrasonic irradiation can
be used as an efficient technique for accelerating organic reactions.[25] Compared
with conventional methods, ultrasonic irradiation is widely applied to promote
numerous organic reaction in good yields and shorter reaction times.[26]
As part of our current studies on developing efficient and simple syntheses
of biologically potential products, herein we report a three-component, one-pot
syntheses of b-unsaturated isoxazol-5-ones and pyrazol-5-ones under ultrasonic
irradiation. The reactions were carried out in water and aqueous ethanol (50%),
respectively (Schemes 1 and 2).
RESULTS AND DISCUSSION
A one-pot reaction of methyl 4-methyl-3-oxovalerate, hydroxylamine, and
aromatic aldehyde afforded 4-arylmethylidene-3-isopropylisoxazol-5-one (4) in

1130
K. ABLAJAN AND H. XIAMUXI
Table 1. Yields for compounds 4 and 6
Entry
R1
R2
Products=yieldsa (%)
Product=yieldsa (%)
1
2
Me
Me
Me
Me
Me
Me
Me
Et
H
4a=83
4b=96
4c=88
4d=86
4e=86
4f=75
4g=92
4a=75
4b=88
4c=80
4d=75
4e=77
4f=63
4g=85
6a=78
6b=90
6c=80
6d=72
6e=84
6f=64
6g=87
6a=70
6b=84
6c=73
6d=64
6e=75
6f=56
6g=80
(Me)2N
MeO
Cl
3
4
5
Me
6
O2N
HO
7
8
H
9
Et
Et
(Me)2N
MeO
Cl
10
11
12
13
14
Et
Et
Me
Et
Et
O2N
HO
aYields of the isolated products.
good yields under promotion of ultrasonic irradiation (Table 1). Accordingly, the
reaction between methyl 4-methyl-3-oxovalerate, phenyl hydrazine, and aromatic
aldehyde produced 4-arylmethylidene-1-phenyl-3-isopropylpyrazol-5-one (6) in good
yield via a one-pot process (Table 1). In the synthesis of compound 4, a high-yield
product was obtained when water was used as a solvent. However, water is not an
ideal solvent for the formation of compound 6. Because of the difference in proper-
ties of hydroxylamine and phenylhydrazine (Schemes 1 and 2), the reaction in 50%
ethanol gave a good yield for compound 6. All reactions were clean and free from
any by-products. It is important to note that the simultaneous mixing of reactants
and catalyst leads to the reaction in 15–35% yield. Thus, the reaction between ethyl
4-methyl-3-oxovalerate and hydroxylamine (or phenyl hydrazine) should be carried
out for 5 min before adding aryl aldehyde. To establish an efficient method, the same
reaction was also performed in ethanol under heating in the absence of ultrasonic
irradiation. As a result, the yields of products 4 and 6 were less than those obtained
under ultrasonic irradiation. So, we suggested that the reaction under ultrasound
irradiation was a best method for the synthesis of these types of compounds.
Furthermore, if ethyl 4-methyl-3-oxovalerate is replaced by methyl 4-methyl-3-
oxovalerate, the yield can be increased around 5–10% (Table 1). We assume that the
removal of methanol was easier than that of ethanol from an intermediate molecule
because of the low steric effect of the methyl group. In addition, the yields of pro-
ducts were significantly affected by the substitutions at the phenyl ring of aldehydes
in which electron-withdrawing groups were more reactive and give better yields.
The structures of products were determined on the bases of infrared (IR),
1H NMR, mass spectra, and elemental analysis. The corresponding spectral data
were in agreement with the proposed structures of products 4 and 6. The 1H
NMR spectrum of 4c exhibited a sharp singlet at 7.40 ppm, which was assigned to
one H atom of CH linked to isoxazole and the phenyl ring. The six protons appeared
as two doublets at 3.01 ppm and were assigned to the H atoms of two CH3, and one
proton appeared as multiplets at 1.38 ppm and was assigned to one H atom of CH in

ISOXAZOL-5-ONES AND PYRAZOL-5-ONES
1131
Scheme 3. Proposed mechanism for the formation of compound 4.
isopropyl group, which was determined by coupling constant J ¼ 6.8 Hz. Two
doublets appeared at 8.44 ppm and 7.01 ppm corresponding to four H atoms at
the p-methoxylated phenyl ring, according to coupling constant J ¼ 8.8 Hz. The mass
spectrum of 4c displayed the molecular ion [M þ H]þ and [M þ Na]þ peaks, which
provide molecular weight information consistent with the theoretical mass weight.
The IR spectrum of 4c showed an absorption band at 1743 cmꢀ1, indicating the
=
presence of lactone C O.
On the basis of the established structures of products, it is reasonable to
=
assume that the first step could involve the condensation of C O of compound 1
with hydroxyl amine 2 to give the intermediate 7, and subsequent reaction with alde-
hyde in the presence of pyridine catalyst leads to the intermediate 8. Intramolecular
reaction between hydroxyl and carbonyl groups followed by the removing of H2O
forms intermediate 9, which could undergo the loss of CH3OH to afford the
isolated products 4 (Scheme 3).
CONCLUSION
In conclusion, we have described an efficient and simple procedure for the syn-
thesis of b-unsaturated isoxazol-5-one and b-unsaturated pyrazol-5-one from methyl
4-methyl-3-oxovalerate, hydroxylamine=phenylhydrazine, and aromatic aldehyde
via a three-component, one-pot reaction. These methods have some advantages such
as green pathways and good product yields.
EXPERIMENTAL
The melting point was determined on a Buchi 2540 microscopic melting appar-
1
atus. The H NMR spectrum was recorded on a Varian Inova 400 instrument with
CDCl3 as solvent and tetramethylsilane (TMS) as internal standard. IR spectrum
was measured with a Bruker-Equinox 55 spectrometer as KBr pellets. The elemental
analysis was performed with a Perkin-Elmer EA-1110 instrument. Mass spectral

1132
K. ABLAJAN AND H. XIAMUXI
(MS) data were obtained on an MDS mass spectrometer. All chemicals were
obtained from commercial suppliers and used without further purification.
General Procedure for the Synthesis of 4-Arylmethylidene-3-
isopropylisoxazol-5-one (4a–4g)
Methyl 4-methyl-3-oxovalerate 1 (4 mmol), hydroxylamine hydrochloride 2
(4 mmol), and pyridine (4 mmol) were mixed in 15 mL water and reacted under ultra-
sonic irradiation for 5 minutes. Aromatic aldehyde 3 (4 mmol) was added to the mix-
ture, and the mixture was further reacted under ultrasonic irradiation for 40 min.
After the reaction was completed, the precipitate was filtered off and washed with
H2O and ether. The crude product was recrystallized from EtOH (90%) to afford
pure product 4.
Data
1
Compound 4a. Yellow crystal, mp 99–101 ꢁC; H NMR (400 MHz, CDCl3)
d: 6.95–8.41 (m, 10H, Ph-H), 7.39 (s, 1H, ArCH¼), 3.01 (m, J ¼ 6.8 Hz, 1H, CH),
1.38 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3075 (Ar-H), 2845 (C-H), 1740
(C O), 1605, 1590, 1550 (C C, C N), 820 (C6H4) cmꢀ1; ESI-MS m=z (%): 238
(M þ Na, 33), 216 (M þ H, 100). Anal. calcd. for C13H13NO2: C, 72.54; H 6.09;
N, 6.08. Found: C, 72.68; H, 6.14; N, 6.39.
=
=
=
1
Compound 4b. Light yellow crystal, mp 167–169 ꢁC; H NMR (400 MHz,
CDCl3) d: 8.42 (d, J ¼ 9.2 Hz, 2H, p-(CH3)2N-C6H4), 6.73 (d, J ¼ 9.2 Hz, 2H,
p-(CH3)2N-C6H4), 7.28 (s, 1H, ArCH¼), 3.16 [s, 6H, N(CH3)2], 2.98 (m, J ¼ 6.8 Hz,
Hz, 1H, CH), 1.37 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3081 (Ar-H), 2969, 2930
(C-H), 1744, (C O); 1619, 1571, 1556, 1528 (C C, C N) cmꢀ1; ESI-MS m=z (%):
281 (M þ Na, 100), 259 (M þ H, 38). Anal. calcd. for C15H18N2O2: C, 69.74; H,
7.02; N, 10.84. Found: C, 69.77; H, 7.08; N, 10.86.
=
=
=
Compound 4c. Pale yellow crystal, mp 110–112 ꢁC; 1H NMR (400 MHz,
CDCl3) d: 8.44 (d, J ¼ 8.8 Hz, 2H, p-H3CO-C6H4), 7.40 (s, 1H, ArCH¼), 7.01 (d,
J ¼ 8.8 Hz, 2H, p-H3CO-C6H4), 3.92 (s, 3H, OCH3), 3.01 (m, J ¼ 6.8 Hz, 1H, CH),
1.38 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3084 (Ar-H), 2977, 2938 (C-H), 1743,
(C O), 1619, 1591, 1557 (C C, C N) cmꢀ1; ESI-MS m=z (%): 274 (M þ K, 34),
283 (M þ Na, 100), 246 (M þ H, 98). Anal. calcd. for C15H18NO3: C, 68.56; H,
6.16; N, 5.71. Found: C, 68.50; H, 6.29; N, 5.55.
=
=
=
1
Compound 4d. Faint yellow crystal, mp 127–129 ꢁC; H NMR (400 MHz,
CDCl3) d: 8.30 (d, J ¼ 8.8 Hz, 2H, p-Cl-C6H4), 7.49 (d, J ¼ 8.8 Hz, 2H, p-Cl-C6H4),
7.42 (s, 1H, ArCH¼), 3.02 (m, J ¼ 6.8 Hz, 1H, CH), 1.39 (d, J ¼ 6.8 Hz, 6H, 2CH3);
=
=
=
IR (KBr) n: 3075 (Ar-H), 2820 (C-H), 1747 (C O), 1645, 1593, 1550 (C C, C N)
cmꢀ1; ESI-MS m=z (%): 250 (M þ H, 100). Anal. calcd. for C13H12ClNO2:
C, 62.53; H, 4.84; N, 5.61. Found: C, 62.57; H, 4.86; N, 5.48.
Compound 4e. Green yellow crystal, mp 92–94 ꢁC; 1H NMR (400 MHz,
CDCl3) d: 8.27 (d, J ¼ 8.0 Hz, 2H, p-H3C-C6H4), 7.44 (s, 1H, ArCH¼), 7.33 (d,
J ¼ 8.0 Hz, 2H, p-H3C-C6H4), 3.02 (m, J ¼ 7.2 Hz, 1H, CH), 2.45 (s, 3H, CH3),

ISOXAZOL-5-ONES AND PYRAZOL-5-ONES
1133
=
1.38 (d, J ¼ 7.2 Hz, 6H, 2CH3); IR (KBr) n: 3085 (Ar-H), 2925 (C-H), 1734 (C O),
1635, 1595, 1564 (C C, C N) cmꢀ1; ESI-MS m=z (%): 261 (M þ K, 12), 252
(M þ Na, 100), 230 (M þ H, 65). Anal. calcd. for C15H18NO2: C, 73.34; H, 6.59;
N, 6.11. Found: C, 73.46; H, 6.47; N, 5.99.
=
=
1
Compound 4f. Red crystal, mp 118–119 ꢁC; H NMR (400 MHz, CDCl3) d:
8.40 (d, J ¼ 8.8 Hz, 2H, ArH), 7.38 (s, 1H, ArCH¼), 7.04 (d, J ¼ 8.8 Hz, 2H, ArH),
3.02 (m, J ¼ 6.8 Hz, 1H, CH), 1.39 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3076
(Ar-H), 2925 (C-H); 1734 (C O), 1611, 1598, 1560 (C C, C N) cmꢀ1; ESI-MS
m=z (%): 283 (M þ Na, 100). Anal. calcd. for C13H12N2O4: C, 61.08; H, 5.49; N,
10.18. Found: C, 61.09; H, 5.51; N, 10.23.
=
=
=
Compound 4g. Yellow crystal, mp 212–214 ꢁC; 1H NMR (400 MHz, CDCl3)
d: 8.40 (d, J ¼ 8.8 Hz, 2H, p-HO-C6H4), 7.39 (s, 1H, ArCH¼), 6.97 (d, J ¼ 8.8 Hz,
2H, p-HO-C6H4), 5.57 (s, 1H, OH), 3.01 (m, J ¼ 6.8 Hz, 1H, CH), 1.37 (d, J ¼ 6.8 Hz,
=
Hz, 6H, 2CH3); IR (KBr) n: 3347 (O-H), 3077 (Ar-H), 2927 (C-H), 1729 (C O),
1607, 1597, 1557 (C C, C N) cmꢀ1; ESI-MS m=z (%): 261 (M þ K, 30), 254
(M þ Na, 100), 232 (M þ H, 85). Anal. calcd. for C14H13NO3: C, 67.52; H, 5.67;
N, 6.06. Found: C, 67.64; H, 5.76; N, 5.93.
=
=
General Procedure for the Synthesis of 4-Arylmethylidene-1-phenyl-
3-isopropylpyrazol-5-one (6a–6g)
Methyl 4-methyl-3-oxovalerate 1 (4 mmol), phenyl hydrazine 5 (4 mmol), and
pyridine (4 mmol) were mixed in 15 mL 50% ethanol and ultrasonically irradiated
for 5 min. Then the aromatic aldehyde 3 (4 mmol) was added to the mixture, and
the mixture was further reacted under ultrasonic irradiation for 40 min. After the
reaction completed, the solid compound was filtered off and washed with H2O
and ether. The crude product was recrystallized from EtOH (90%) to afford pure
product 6.
Data
Compound 6a. Yellow crystal, mp 183–185.1 ꢁC; 1H NMR (400 MHz,
CDCl3) d: 6.93–8.27 (m, 10H, Ph-H), 7.30 (s, 1H, ArCH¼), 3.07 (m, J ¼ 7.2 Hz,
1H, CH), 1.39 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3075, 2970 (C-H), 1668
(C O), 1615, 1593, 1560 (C C, C N) cmꢀ1; ESI-MS m=z (%): 313 (M þ Na, 33),
291 (M þ H, 100). Anal. calcd. for C19H18N2O: C, 78.59; H, 6.25; N, 9.65. Found:
C, 78.63; H, 6.28; N, 9.49.
=
=
=
Compound 6b. Brown crystal, mp 151–153 ꢁC; 1H NMR (400 MHz, CDCl3)
d: 8.57 (d, J ¼ 9.2 Hz, 2H, p-(CH3)2N-C6H4), 7.15–8.04 (m, 5H, Ph-H), 7.32 (s, 1H,
ArCH¼), 6.73 (d, J ¼ 9.2 Hz, 2H, p-(CH3)2N-C6H4), 3.13 [s, 6H, N(CH3)2], 3.06 (m,
J ¼ 6.8 Hz, 1H, CH), 1.38 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3075 (Ar-H), 2970,
2927 (C-H), 1652 (C O), 1620, 1596, 1563, 1546 (C C, C N) cmꢀ1; ESI-MS m=z
(%): 372 (M þ K, 100), 356 (M þ Na, 100), 334 (M þ H, 68). Anal. calcd. for
C21H23N3O: C, 75.65; H, 6.95; N, 12.60. Found: C, 75.69; H, 6.98; N, 12.67.
=
=
=

1134
K. ABLAJAN AND H. XIAMUXI
Compound 6c. Orange crystal, mp 101–103 ꢁC; 1H NMR (400 MHz, CDCl3)
d: 8.58 (d, J ¼ 9.2 Hz, 2H, p-H3CO-C6H4), 7.17–8.01 (m, 5H, Ph-H), 7.39 (s, 1H,
ArCH¼), 7.01 (d, J ¼ 9.2 Hz, 2H, p-H3CO-C6H4), 3.91 (s, 6H, OCH3), 3.09 (m,
J ¼ 6.8 Hz, 1H, CH), 1.39 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3056, IR (KBr)
=
=
n: 3056 (Ar-H), 2964, 2927 (C-H), 1677 (C O), 1597, 1585, 1549, 1512 (C C,
C N) cmꢀ1; ESI-MS m=z (%): 343 (M þ Na, 100), 321 (M þ H, 68). Anal. calcd.
=
for C20H20N2O2: C, 74.98; H, 6.29; N, 8.74. Found: C, 75.01; H, 6.32; N, 8.77.
Compound 6d. Orange crystal, mp 280–282 ꢁC; 1H NMR (400 MHz, CDCl3)
d: 8.61 (d, J ¼ 8.8 Hz, 2H, ArH), 7.21–8.12 (m, 5H, Ph-H), 7.38 (s, 1H, ArCH¼), 7.06
(d, J ¼ 9.2 Hz, 2H, ArH), 3.07 (m, J ¼ 8.8, 1H, CH), 1.38 (d, J ¼ 7.2, 6H, 2CH3); ꢀIR1
=
=
=
(KBr) n: 3076, 2974 (C-H), 1679 (C O), 1605, 1589, 1559 (C C, C N) cm
;
ESI-MS m=z (%): 347 (M þ Na, 33), 327 (M þ 2 þ H, 35), 325 (M þ H, 100). Anal.
calcd. for C19H17ClN2O: C, 70.26; H, 5.28; N, 8.62. Found: C, 70.29; H, 5.34; N, 8.64.
Compound 6e. Orange crystal, mp 114–116 ꢁC; 1H NMR (400 MHz, CDCl3)
d: 8.41 (d, J ¼ 8.4 Hz, 2H, p-CH3-C6H4), 7.16–8.00 (m, 5H, Ph-H), 7.32 (s, 1H,
ArCH¼), 7.31 (d, J ¼ 9.2 Hz, 2H, p-CH3-C6H4), 3.10 (m, J ¼ 6.8 Hz, 1H, CH),
2.44 (s, 3H, CH3), 1.40 (d, J ¼ 7.2 Hz, 6H, 2CH3); IR (KBr) n: 3012, 2910 (C-H),
1677 (C O), 1604, 1595, 1569 (C C, C N) cmꢀ1; ESI-MS m=z (%): 327 (M þ Na,
Na, 33), 305 (M þ H, 100). Anal. calcd. for C20H20N2O: C, 78.92; H, 6.62; N, 9.20.
Found: C, 78.95; H, 6.76; N, 9.25.
=
=
=
1
Compound 6f. Scarlet crystal, mp 161–163 ꢁC; H NMR (400 MHz, CDCl3)
d: 8.58 (d, J ¼ 9.2 Hz, 2H, ArH), 7.17–8.01 (m, 5H, Ph-H), 7.39 (s, 1H, ArCH¼), 7.0
(d, J ¼ 9.2 Hz, 2H, ArH), 3.91 (s, 6H, OCH3), 3.08 (m, J ¼ 7.2 Hz, 1H, CH), 1.39 (d,
=
J ¼ 7.2 Hz, 6H, 2CH3); IR (KBr) n: 3072, 2964 (C-H), 1687 (C O), 1607,1592, 1564
=
=
(C C, C N) cm-1; ESI-MS m=z (%): 358 (M þ Na, 100), 336 (M þ H, 63). Anal.
calcd. for C19H17N3O3: C, 68.05; H, 5.11; N, 12.50. Found: C, 68.08; H, 5.15; N,
12.58.
Compound 6g. Scarlet crystal, mp 268–270 ꢁC; 1H NMR (400 MHz, CDCl3)
d: 8.51 (d, J ¼ 8.8 Hz, 2H, p-HO-C6H4), 7.43 (s, 1H, ArCH¼), 7.18–7.96 (m, 5H,
Ph-H), 7.00 (d, J ¼ 8.8 Hz, 2H, p-HO-C6H4), 6.21 (s, 1H, OH), 3.10 (m, J ¼ 6.8 Hz,
Hz, 1H, CH), 1.40 (d, J ¼ 6.8 Hz, 6H, 2CH3); IR (KBr) n: 3334 (O-H), 3068, 2975
(C-H), 1669 (C O), 1596, 1589, 1563 (C C, C N) cmꢀ1; ESI-MS m=z (%): 329
(M þ Na, 100). Anal. calcd. for C19H18N2O2: C, 74.49; H, 5.92; N, 9.14. Found:
C, 74.51; H, 5.95; N, 9.17.
=
=
=
ACKNOWLEDGMENT
This research was supported by the Natural Science Foundation of Xinjiang
Science Technology Agency (No. 2009211A02).
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