Synthesis of novel 9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e] [1,2,4] triazolo[1,5-c]pyrimidin-11(10H)-one derivatives

Article abstract of DOI:10.3184/174751914X14053476598397

Novel 9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c] pyrimidin-11(10H)-one derivatives were synthesised by the reactions of triethyl orthoformate or aromatic aldehydes with chromeno[2,3-d]pyrimidine derivatives, which were prepared by

Full text of DOI:10.3184/174751914X14053476598397

4
80 RESEARCH PAPER
VOL. 38 AUGUST, 480–485
JOURNAL OF CHEMICAL RESEARCH 2014
Synthesis of novel 9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e] [1,2,4]
triazolo[1,5-c]pyrimidin-11(10H)-one derivatives
a
a
b
a
a,b
Zhong-Xia Wang , Bei Li , Zheng Xing , Li-Zhuang Chen and Guang-Fan Han *
a
Department of Applied Chemistry, School of Environmental and Chemical Engineering, Jiangsu University of Science & Technology, Zhenjiang,
Jiangsu 212003, P.R. China
bZhenjiang College, Zhenjiang, Jiangsu 212000, P.R. China
Novel 9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one derivatives were synthesised
by the reactions of triethyl orthoformate or aromatic aldehydes with chromeno[2,3-d]pyrimidine derivatives, which were
prepared by the reactions of hydrazine monohydrate and formimidate derivatives. Formimidate were synthesised by the
reactions of 2-amino-7,7-dimethyl-5-oxo-4-aryl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives and triethyl
orthoformate. The structures of 12-(4-methoxyphenyl)-9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]
pyrimidin-11(10H)-one was determined by single crystal X-ray diffraction analysis.
Keywords: chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-11(10H)-one, formimidate, chromeno[2,3-d]pyrimidine
The triazolo heterocyclic ring system has received
considerable attention among synthetic chemists in recent
years, because molecules bearing this feature display a
wide range of biological activities in medicinal chemistry,
such as antioxidant, antimalarial, anti-ocular hypertension
Results and discussion
The synthetic route to the title compounds are shown in
Scheme 1. 2-Amino-7,7- dimethyl-5-oxo-4-aryl-5,6,7,8-
tetrahydro-4H-chromene-3-carbonitrile derivatives
synthesised by the reaction of 5,5-dimethylcyclohexane-
1,3-dione with 2-arylylidene malononitrile derivatives 1,
2 were
1–4
10
properties.
Furthermore, 1,2,4-triazolo[1,5-c]pyrimidines
which were prepared by the reaction of aromatic aldehydes
exhibited antimicrobial activities such as antiviral,
11
5
–7
and malononitrile with KF·2H O as catalyst in ethanol.
antibacterial and antithrombotic agents. The pyrazolo[4,3-e]
1,2,4]triazolo[1,5-c]pyrimidine nucleus has been recognised
2
Compounds 2 and excess triethyl orthoformate were heated
to give ethyl N-(4-aryl-3-cyano-7,7-dimethyl-5-oxo-5,6,7,8-
tetrahydro-4H-chromen-2-yl)formimidate derivatives 3, which
reacted with hydrazine monohydrate to afford 3-amino-5-aryl
[
as a promising template for the development of new adenosine
8
receptor antagonists. In addition, antigenotoxic activity
has been found in the pyrano[3,2-e][1,2,4]triazolo[1,5-c]
4
-imino-8,8-dimethyl-5,7,8,9-tetrahydro-3H-chromeno[2,3-d]
9
pyrimidine derivatives.
pyrimidin-6(4H)-one derivatives 4. 12-Aryl-9,9-Dimethyl-8,12-
dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-
We now report the structural modification of certain
biological active heterocyclic nuclei through the study of the
synthesis of several novel analogues of chromeno[3,2-e][1,2,4]
triazolo[1,5-c]pyrimidine derivatives with the aim of enhancing
their biological activities (Scheme 1).
11(10H)-one derivatives 5 and 6 were synthesised by the reaction
of compounds 4 with excess triethyl orthoformate or aromatic
aldehydes. The melting points and yields of compounds 3, 4, 5
and 6 are shown in Tables 1, 2, 3 and 4, respectively.
R1
R1
O
NC
CN
O
O
CH(OEt)3
CN
CN
O
CHO
R1
O
NH2
O
N=CHOEt
2
3
NH NH2
2
R1
R
2
R1
R1
CHO
O
N
O
NH
N
O
N
NH2
N
CH(OEt)3
N
N
R2
N
O
N
O
N
O
N
Scheme 1
*
Correspondent. E-mail: gf552002@163.com

JOURNAL OF CHEMICAL RESEARCH 2014 481
1
The data of IR, H NMR, elemental analysis shown in the
peak of 12-H. The structures of these compounds were further
proved by their IR spectra through several typical absorption
experimental section are in accordance with the chemical
structures of the target compounds.
In the H NMR spectrum of compound 3c, a sharp single
–1
–1
bands of 1659 cm for (C=O), 2892, 2952 cm for (–CH ), and
3
1
–1
3118 cm for (aromatic-H).
proton peak at δ 4.46 was the characteristic absorption proton
peak of 4-H. The structures of these compounds were further
testified by their IR spectra through several typical absorption
Interaction of compounds 3 with hydrazine monohydrate in
absolute ethanol gave the key intermediates compounds 4. Note
that compounds 3 can be reduced to afford the raw material 2
if excess hydrazine monohydrate 99% was used in the reaction.
This may be attributed to the reaction of excess hydrazine
monohydrate 99% with the iminoether 3 that took place with
preferential elimination of ethyl formate hydrazone rather than
cyclisation to give the pyrimidine ring. At the high activity,
hydrazine monohydrate was added dropwise to the reaction
system; the optimal reaction temperature was 0–5 °C. If the
temperature of the reaction was higher, the reaction was too
intense to yield compounds 4. Moreover, all reagents used in
reaction were dried.
–1
–1
–1
bands of 1624 cm for (C=N), 2220 cm for (–CN), 2931 cm
–
1
–1
for (–CH ), 2980 cm for (–CH ), 3053 cm for (CH-aromatic).
2
1
3
In the H NMR spectrum of compound 4c, a sharp single
proton peak at δ 4.66 was the characteristic absorption proton
peak of 5-H. The structures of these compounds were further
testified by their IR spectra through several typical absorption
bands of 1660 cm for (C=O), 2959 cm for (–CH ), 3190 cm
for (cyclohexane–CH ), and 3283 cm for (N–H).
In the H NMR spectrum of compound 5c, a sharp single
proton peak at δ 5.48 was the characteristic absorption proton
peak of 12-H. The structures of these compounds were further
proved by their IR spectra through several typical absorption
bands of 1656 cm for (C=O), 2837, 2967 cm for (–CH ), and
083 cm for (aromatic-H).
12
–1
–1
–1
3
–1
2
1
Originally, the final compounds 5 were obtained by reaction
of compounds 4 with triethyl orthoformate (1:1) with piperidine
–1
–1
or KF·2H O as catalysts under reflux in ethanol. However, we
2
3
–1
found the yield was very low (ca 20%). In order to increase the
productivity, we directly added excessive triethyl orthoformate
at reflux. In this way, the reaction temperature was improved
from 78 to 143 °C, and the yields reached up to around 80%. In
addition, the reactant compounds 4 and triethyl orthoformate
were all purified.
In the synthesis process of compounds 6, a series of aromatic
aldehydes were involved. However, it was found that the yield
of aromatic aldehydes containing the electron-withdrawing
3
1
In the H NMR spectrum of compound 6c, a sharp single
proton peak at δ 5.44 was the characteristic absorption proton
Table 1 Synthesis of 4-aryl-ethyl N-(3-cyano-7,7-dimethyl-5-oxo-5,6,7,8-
tetrahydro-4H-chromen-2-yl)formimidate derivatives 3a–ga
Derivative
R
M.p./°C
Yield/%b
3
3
3
3
3
a
b
c
d
e
H
216–218
124–126
126–128
116–118
212–214
114–116
154–156
72
75
70
80
76
72
70
4-OCH3
3,4-(OCH3)2
4-CH3
2,4-Cl2
3-NO2
2-Cl
Table 4 Synthesis of 2,12-diaryl-9,9-dimethyl-8,12-dihydro-9H-chromeno
[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H )-one derivatives 6a–ga
3
f
R1
R2
Yield/%b
Derivative
M.p./°C
3
g
6
6
6
6
6
a
b
c
d
e
H
4-OCH3
4-OCH3
3,4-(OCH3)2
4-OCH3
3,4-(OCH3)2
4-OCH3
208–210
136–138
132–134
118–120
156–158
118–120
214–216
70
75
73
72
77
68
73
aReaction conditions: 15 mL triethyl orthoformate, 10 mmol compounds 2,
4-OCH3
4-OCH3
3,4-(OCH3)2
3,4-(OCH3)2
4-CH3
reflux.
b
Isolated yield.
6
6
f
g
Table 2 Synthesis of 3-amino-4-imino-8,8-dimethyl-3,4,8,9-5-phenyl-
4-CH3
3,4-(OCH3)2
a
tetrahydro-5H-chromeno[2,3-d ]pyrimidin-6(7H )-one derivatives 4a–g
aReaction condition: 15 mL ethanol, 10 mmol compounds 4, 10 mmol
Derivative
R
M.p./°C
Yield/%b
aromatic aldehydes, 1 drop piperidine, reflux.
b
4
4
4
4
4
a
b
c
d
e
H
214–216
178–180
174–176
176–178
178–180
202–204
166–168
61
70
73
79
75
76
72
Isolated yield.
4-OCH3
3,4-(OCH3)2
4-CH3
2,4-Cl2
3-NO2
Table 5 Crystallographic data for compound 5b
Empirical formula
C H N O
21 20 4 3
4
f
Formula weight
376.41
4
g
2-Cl
Wavelength/nm
Crystal system
Space group
a/Å
0.71073
Orthorhombic
P 2 2 2
6.898(3)
13.722(6)
19.927(8)
90.00
90.00
90.00
1886.4(14)
4
aReaction conditions: 10 mL ethanol, 5 mmol 99% hydrazine monohydrate,
5
mmol formimidate derivatives 3, room temperature.
b
1 1 1
Isolated yield.
b/Å
Table 3 Synthesis of 12-aryl-9,9-dimethyl-8,12-dihydro-9H-chromeno
a
c/Å
[
3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H )-one derivatives 5a–g
o
Yield/%b
α/( )
Derivative
R
M.p./°C
β/(o)
5
5
5
5
5
a
b
c
d
e
H
188–190
208–210
202–204
206–208
222–224
214–216
238–240
65
72
76
73
63
63
66
γ/(o)
4-OCH3
3,4-(OCH3)2
4-CH3
Volume/Å3
Z
2,4-Cl2
–3
Calculated density/g·cm
Absorption coefficient/mm
F (000)
Final R indices [I>2s(I)]
R indices (all data)
1.325
0.091
5
f
3-NO2
2-Cl
–1
5
g
792
aReaction condition: 10 mL triethyl orthoformate, 5 mmol compounds 4,
1
2
R =0.0526, wR = 0.1088
R =0.1188, wR = 0.1522
reflux.
1
2
b
Isolated yield.

4
82 JOURNAL OF CHEMICAL RESEARCH 2014
group was lower than that containing the electron-donating
group (such as methoxy) in the same reaction time. It was in
the presence of the electron-donating group, that the activity
of aromatic aldehydes was increased. So, aromatic aldehydes
containing the methoxy group were incorporated into the
experiment.
aryl-4-imino-8,8-dimethyl-3,4,8,9-tetrahydro-5H-chromeno[2,3-d]
pyrimidin-6(7H)-one derivatives 4 as crystalline powder.
Synthesis of 12-aryl-9,9-dimethyl-8,12-dihydro-9H-chromeno[3,2-e]
[1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one derivatives (5a–g);
general procedure
A solution of compounds 4 (5 mmol) and triethyl orthoformate (10 mL)
was heated to reflux for 6 h. After cooling to room temperature, the
precipitate was filtered off and recrystallised from ethanol to yield
12-aryl-9,9-dimethyl-8,12-dihydro-9H-chromeno-[3,2-e][1,2,4]
triazolo[1,5-c]pyrimidin-11(10H)-one derivatives 5 as crystalline
powder.
Conclusion
The present study synthesised a series of novel 9,9-dimethyl-
8
,12-dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]
pyrimidin-11(10H)-one derivatives from chromeno [2,3-d]
pyrimidine in good yields in a route that is also useful for drug
research. Moreover, the new synthetic route offers several
advantages including simple operation, available raw materials,
and good yields, which makes it an attractive process for the
synthesis of the title compounds.
Synthesis of 2,12-diaryl-9,9-dimethyl-8,12-dihydro-9H-chromeno
[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one derivatives (6a–g);
general procedure
Piperidine (one drop) as a catalyst was added to a solution of the
corresponding compounds 4 (10 mmol) and aromatic aldehydes
(
10 mmol) in ethanol (15 mL). The mixture was stirred at 80 °C for 4 h,
Experimental
the progress of the reaction was monitored by TLC. Then the resultant
mixture was cooled to room temperature. The filtrate was purified
by silica gel flash chromatography using ethyl acetate/petroleum
ether (2:1) as the eluent to obtain pure 2,12-diaryl-9,9-dimethyl-
8,12-dihydro-9H-chromeno-[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-
11(10H)-one derivatives 6.
Melting points were determined by an electrothermal apparatus and
the temperature was uncorrected. Microanalysis was performed
by the PerkinElmer 2400 Microanalytical Service. IR spectra were
1
determined on a PerkinElmer 1700 spectrophotometer. H NMR
spectra were recorded on a Bruker ARX-400 instrument. Mass
spectra were recorded by JMS-DX300 mass spectrometer with an
ionisation potential of 70 eV. All reactions were monitored by TLC,
which carried out on 0.2 mm silica GF254 (Merck) plates using UV
light (254 and 365 nm) for detection.
Single-crystal X-ray crystallography
X-ray diffraction experiments were carried out using Bruker SMART
APEX CCD with MoKα radiation (λ=0.71073 Å) at 291(2) K. Data
collection, cell refinement, and data reduction were performed by
using the Crystal Clear software package. The structures of 5b were
solved by direct methods and refined by the full-matrix method based
on F2 using the SHELXTL software package. All non-hydrogen
atoms were refined anisotropically, and the positions of all hydrogen
atoms were generated geometrically. Crystallographic data (excluding
structure factors) for the structure in this paper have been deposited
with the Cambridge Crystallographic Data Centre as supplementary
publication CCDC Nos. 1005559. Crystal data for 5b: C H N O ,
Synthesis of ethyl N-(4-aryl-3-cyano-7,7-dimethyl-5-oxo-5,6,7,8-
tetrahydro-4H-chromen-2-yl)formimidate derivatives (3a–g); general
procedure
The ethyl 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-
chromene-3-carbonitrile derivatives 2 (10 mmol) was added to excess
triethyl orthoformate (15 mL) and refluxed for 6 h. The resulting
dark brown solution was allowed to cool to room temperature and
evaporated under reduced pressure to give a brown residue. Then the
crude product was filtered off and recrystallised from ethanol.
21
20
4
3
M =376.41, orthorhombic P2 2 2 , a=6.898(3) Å, b=13.722(6)
Å, c=19.927(8) Å, V=1886.4(14) Å , Z=4, D =1.325 g cm , R
(
w
1 1 1
3
−3
1
c
Synthesis of 3-amino-5-aryl-4-imino-8,8-dimethyl-3,4,8,9-tetrahydro-
2
−1
I > 2σ) = 0.0526, wR = 0.1088, μ = 0.091 m m , S=1.000; Flack
5H-chromeno[2,3-d]pyrimidin-6(7H)-one derivatives (4a–g); general
value=0.4 (10).
procedure
The single crystal structure of 5b was determined by single-crystal
X-ray diffraction analysis (Figs 1 and 2) and a summary of the crystal
data and structure refinement is presented in Table 5.
Ethyl N-(3-cyano-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-
Compounds 3 (5 mmol) were dissolved in ethanol (10 mL), and
9
9% hydrazine monohydrate (5 mmol) was added dropwise to the
solution. The solution was stirred at 0–5 °C for 3 h, during which
time precipitate separated out from the solution. The precipitate was
filtered off and recrystallised from ethanol to afford 3-amino-5-
4
H-chromen-2-yl)formimidate (3a): Yield 72%; m.p. 216–218 °C.
–1
1
IR (KBr, ν, cm ): 3053, 2978, 2935, 2213, 1621; H NMR (CDCl ,
3
4
00 MHz) δ 1.08 (s, 3H, –CH ), 1.14 (s, 3H, –CH ), 1.31–1.40 (t,
3 3
8
J=7.1 Hz, 3H, –OCH CH ), 2.21–2.31 (m, 2H, C –H), 2.48–2.56 (m,
2
3
Fig. 1 Molecular structure of compound 5b.
Fig. 2 Packing diagram of compound 5b in the unit cell.

JOURNAL OF CHEMICAL RESEARCH 2014 483
6
2
H, C –H), 4.38–4.44 (q, J=7.1 Hz, 2H, –OCH CH ), 4.54 (s, 1H,
calcd for C H N O : C, 67.84; H, 5.99; N, 16.66; found C, 67.32; H,
6.08; N, 16.76%.
3-Amino-4-imino-5-(4-methoxyphenyl)-8,8-dimethyl-3,4,8,9-
2
3
19 20
4
2
4
C –H), 7.22–7.35 (m, 5H, Ph–H), 8.26 (s, 1H, –N=CHOEt). Anal. calcd
for C H N O : C, 71.98; H, 6.33; N, 7.99; found C, 71.83; H, 6.20; N,
2
1
22
2
3
7
.81%.
Ethyl N-(3-cyano-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-
tetrahydro-4H-chromen-2-yl)formimidate (3b): Yield 75%; m.p.
tetrahydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one (4b): Yield 70%;
–1
1
m.p. 178–180 °C. IR (KBr, ν, cm ): 3315, 3277, 3191, 2964, 1662; H
NMR (CDCl , 400 MHz) δ 0.99 (s, 3H, –CH ), 1.11 (s, 3H, –CH ),
3
3
3
–1
1
9
7
124–126 °C. IR (KBr, ν, cm ): 3050, 2985, 2924, 2223, 1620; H NMR
2.17–2.28 (dd, J =16.4 Hz, J =27.1 Hz, 2H, C –H), 2.54 (s, 2H, C –H),
1 2
3.76 (s, 3H, –OCH ), 4.68 (s, 1H, C –H), 4.76 (s, 2H, –NH ), 6.80–6.82
5
(CDCl , 400 MHz) δ 1.05 (s, 3H, –CH ), 1.12 (s, 3H, –CH ), 1.35–1.38
3
3
3
3
2
(
2
t, J=7.1 Hz, 3H, –OCH CH ), 2.19–2.28 (dd, J =16.4 Hz, J =21.7 Hz,
(d, J=8.6 Hz, 2H, 3′+5′-H), 7.26–7.28 (d, J=8.6 Hz, 2H, 2′+6′-H),
2
3
1
2
8
6
2
H, C –H), 2.48 (s, 2H, C –H), 3.77 (s, 3H, –OCH ), 4.36–4.42
8.03 (m, 1H, C –H). Anal. calcd for C H N O : C, 65.56; H, 6.05; N,
3
20 22
4
3
4
(q, J=7.0 Hz, 2H, –OCH CH ), 4.47 (s, 1H, C –H), 6.82–6.85 (d,
15.29; found C, 65.42; H, 6.25; N, 15.34%.
2
3
J=8.4 Hz, 2H, 3′+5′-H), 7.17–7.19 (d, J=8.5 Hz, 2H, 2′+6′-H), 7.26
3-Amino-5-(3,4-dimethoxyphenyl)-4-imino-8,8-dimethyl-3,4,8,9-
(
7
s, 1H, –N=CHOEt). Anal. calcd for C H N O : C, 69.46; H, 6.36; N,
.36; found C, 69.32; H, 6.25; N, 7.30%.
Ethyl N-(3-cyano-4-(3,4-dimethoxyphenyl)-7,7-dimethyl-5-oxo-
tetrahydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one (4c): Yield 73%;
2
2
24
2
4
–1
1
m.p. 174–176 °C. IR (KBr, ν, cm ): 3283, 3190, 2959, 1660; H NMR
(CDCl , 400 MHz) δ 0.99 (s, 3H, –CH ), 1.11 (s, 3H, –CH ), 2.18–2.28
3
3
3
9
7
5
,6,7,8-tetrahydro-4H-chromen-2-yl)formimidate (3c): Yield 70%;
(dd, J =16.4 Hz, J =24.5 Hz, 2H, C –H), 2.53 (s, 2H, C –H), 3.81–3.84
1 2
(d, 6H, 2×–OCH ), 4.66 (s, 1H, C –H), 4.77 (s, 2H, –NH ), 6.75–6.77
–1
5
m.p. 126–128 °C. IR (KBr, ν, cm ): 3053, 2980, 2931, 2220, 1624;
3
2
1
H NMR (CDCl , 400 MHz) δ 1.08 (s, 3H, –CH ), 1.13 (s, 3H, –CH ),
(d, J=8.7 Hz, 1H, 2′-H), 6.86–6.88 (d, J=6.1 Hz, 2H, 5′+6′-H), 8.03
3
3
3
2
1
.35–1.38 (t, J=7.1 Hz, 3H, –OCH CH ), 2.21–2.30 (dd, J =16.5 Hz,
(s, 1H, C –H). Anal. calcd for C H N O : C, 63.62; H, 6.10; N, 14.13;
2
3
6
1
21 24
4
4
8
J =20.1 Hz, 2H, C –H), 2.49 (s, 2H, C –H), 3.84–3.87 (d, 6H, 2×–
OCH ), 4.37–4.42 (q, J=7.0 Hz, 2H, –OCH CH ), 4.46 (s, 1H, C –H),
found C, 63.42; H, 6.34; N, 14.17%.
3-Amino-5-(p-tolyl)-4-imino-8,8-dimethyl-3,4,8,9-tetrahydro-
2
4
3
2
3
6
.76–6.82 (m, 3H, Ph–H), 8.23 (s, 1H, –N=CHOEt). Anal. calcd for
5H-chromeno[2,3-d]pyrimidin-6(7H)-one (4d): Yield 69%; m.p.
–1
1
C H N O : C, 67.30; H, 6.38; N, 6.82; found C, 67.21; H, 6.31; N,
176–178 °C. IR (KBr, ν, cm ): 3318, 3287, 3195, 2966, 1659; H NMR
(CDCl , 400 MHz) δ 0.98 (s, 3H, –CH ), 1.10 (s, 3H, –CH ), 2.16–2.27
2
3
26
2
5
6.90%.
3
3
3
9
Ethyl N-(3-cyano-7,7-dimethyl-5-oxo-4-p-tolyl-5,6,7,8-tetrahydro-
(dd, J =16.4 Hz, J =28.5 Hz, 2H, C –H), 2.27 (s, 3H, 4′–CH ), 2.53
1 2 3
(s, 2H, C –H), 4.67 (s, 1H, C –H), 4.78 (s, 2H, –NH ), 7.06–7.08 (d,
7
5
4H-chromen-2-yl)formimidate (3d): Yield 80%; m.p. 116–118 °C.
2
–1
1
IR (KBr, ν, cm ): 3052, 2980, 2921, 2224, 1618; H NMR (CDCl ,
4
J=7.9 Hz, 2H, 3′+5′-H), 7.21–7.28 (d, J=8.0 Hz, 2H, 2′+6′-H), 7.99
3
2
00 MHz) δ 1.06 (s, 3H, –CH ), 1.12 (s, 3H, –CH ), 1.34–1.38 (t,
(s, 1H, C –H). Anal. calcd for C H N O : C, 68.55; H, 6.33; N, 15.99;
3
3
20 22
4
2
J=7.1 Hz, 3H, –OCH CH ), 2.18–2.29 (dd, J =16.4 Hz, J =22.3 Hz,
found C, 68.67; H, 6.21; N, 15.89%.
3-Amino-5-(2,4-dichlorophenyl)-4-imino-8,8-dimethyl-3,4,8,9-
2
3
1
2
8
6
2
H, C –H), 2.29 (s, 3H, –CH ), 2.48 (s, 2H, C –H), 4.35–4.41 (q,
3
4
J=7.1 Hz, 2H, –OCH CH ), 4.48 (s, 1H, C –H), 7.09–7.16 (m, 4H, Ph–
tetrahydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one (4e): Yield 75%;
2
3
–1
1
H), 8.23 (s, 1H, –N=CHOEt). Anal. calcd for C H N O : C, 72.50; H,
m.p. 178–180 °C. IR (KBr, ν, cm ): 3335, 3293, 3195, 2957, 1663; H
NMR (CDCl , 400 MHz) δ 1.02 (s, 3H, –CH ), 1.14 (s, 3H, –CH ),
2
2
24
2
3
6
.64; N, 7.69; found C, 72.38; H, 6.50; N, 7.82%.
3
3
3
9
7
Ethyl N-(3-cyano-4-(2,4-dichlorophenyl)-7,7-dimethyl-5-oxo-
2.17–2.31 (dd, J =16.4 Hz, J =37.1 Hz, 2H, C –H), 2.57 (s, 2H, C –H),
1 2
5
5
,6,7,8-tetrahydro-4H-chromen-2-yl)formimidate (3e): Yield 76%;
4.78 (s, 2H, –NH ), 5.13 (s, 1H, C –H), 7.20 (s, 2H, 5′+6′-H), 7.37 (s,
2
–1
1
2
m.p. 212–214 °C. IR (KBr, ν, cm ): 3047, 2981, 2934, 2218, 1622; H
NMR (CDCl , 400 MHz) δ 1.07 (s, 3H, –CH ), 1.12 (s, 3H, –CH ),
1H, 3′-H), 8.04 (m, 1H, C –H). Anal. calcd for C H Cl N O : C, 56.31;
1
9
18
2
4
2
H, 4.48; N, 13.82; found C, 56.43; H, 4.38; N, 13.75%.
3
3
3
1
.35–1.38 (t, J=7.1 Hz, 3H, –OCH CH ), 2.18–2.28 (dd, J =16.4 Hz,
3-Amino-4-imino-8,8-dimethyl-5-(3-nitrophenyl)-3,4,8,9-
tetrahydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one (4f): Yield 76%;
2
3
6
1
8
J =26.2 Hz, 2H, C –H), 2.48 (s, 2H, C –H), 4.37–4.42 (q, J=7.1 Hz,
2
4
–1
1
2
1
6
H, –OCH CH ), 4.94 (s, 1H, C –H), 7.20 (s, 2H, 5′+6′-H), 7.37 (s,
m.p. 202–204 °C. IR (KBr, ν, cm ): 3331, 3290, 3188, 2957, 1659; H
NMR (CDCl , 400 MHz) δ 0.99 (s, 3H, –CH ), 1.13 (s, 3H, –CH ),
2
3
H, 3′-H), 8.24 (s, 1H, –N=CHOEt). Anal. calcd for C H Cl N O : C,
21
20
2
2
3
3
3
3
9
0.15; H, 4.81; N, 6.68; found C, 59.92; H, 4.69; N, 6.80%.
Ethyl N-(3-cyano-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-
tetrahydro-4H-chromen-2-yl)formimidate (3f): Yield 72%; m.p.
2.19–2.30 (dd, J =16.4 Hz, J =40.9 Hz, 2H, C –H), 2.55–2.63 (dd,
1 2
J =18.0 Hz, J =22.6 Hz, 2H, C –H), 4.71 (s, 2H, –NH ), 4.88 (s, 1H,
C –H), 7.48–7.52 (t, J=7.9 Hz, 1H, 5′-H), 7.82–7.83 (d, J=7.6 Hz, 1H,
6′-H), 8.08 (s, 1H, 4′-H), 8.10 (s, 1H, C –H), 8.16 (s, 1H, 2′-H). Anal.
7
1
5
2
2
–1
1
2
114–116 °C. IR (KBr, ν, cm ): 3052, 2983, 2924, 2220, 1621;
H
NMR (CDCl , 400 MHz) δ 1.07 (s, 3H, –CH ), 1.14 (s, 3H, –CH ),
calcd for C H N O : C, 59.84; H, 5.02; N, 18.36; found C, 59.79; H,
3
3
3
19 19
5
4
1
.36–1.39 (t, J=7.1 Hz, 3H, –OCH CH ), 2.20–2.31 (dd, J =16.4 Hz,
5.12; N, 18.33%.
2
3
1
8
J =26.2 Hz, 2H, C –H), 2.49–2.60 (dd, J =17.9 Hz, J =24.1 Hz, 2H,
3-Amino-5-(2-chlorophenyl)-4-imino-8,8-dimethyl-3,4,8,9-
tetrahydro-5H-chromeno[2,3-d]pyrimidin-6(7H)-one (4g): Yield
2
1
2
6
4
C –H), 4.39–4.44 (q, J=7.1 Hz, 2H, –OCH CH ), 4.65 (s, 1H, C –H),
2
3
–1
7
8
.50–7.54 (t, J=7.9 Hz, 1H, 5′-H), 7.72–7.74 (d, J=7.5 Hz, 1H, 6′-H),
.07–8.12 (m, 2H, 2′+4′-H), 8.29 (s, 1H, –N=CHOEt). Anal. calcd for
C H N O : C, 63.79; H, 5.35; N, 10.63; found C, 63.61; H, 5.24; N,
72%; m.p. 166–168 °C. IR (KBr, ν, cm ): 3329, 3297, 3187, 2948,
1
1670; H NMR (CDCl , 400 MHz) δ 1.02 (s, 3H, –CH ), 1.13 (s, 3H,
3
3
9
–CH ), 2.17–2.31 (dd, J =16.4 Hz, J =43.4 Hz, 2H, C –H), 2.57 (s,
21
21
3
5
3
1
2
7
5
1
0.71%.
Ethyl N-(4-(2-chlorophenyl)-3-cyano-7,7-dimethyl-5-oxo-5,6,7,8-
tetrahydro-4H-chromen-2-yl)formimidate (3g): Yield 70%; m.p.
2H, C –H), 4.72 (s, 2H, –NH ), 5.17 (s, 1H, C –H), 7.13–7.16 (m, 1H,
2
6′-H), 7.19–7.22 (m, 1H, 4′-H), 7.25–7.28 (m, 1H, 5′-H), 7.34–7.35 (d,
J=7.8 Hz, 1H, 3′-H), 8.02 (s, 1H, C –H). Anal. calcd for C H ClN O :
C, 61.54; H, 5.16; N, 15.11; found C, 61.43; H, 5.20; N, 15.07%.
2
19
19
4
2
–1
1
154–156 °C. IR (KBr, ν, cm ): 3051, 2978, 2934, 2217, 1625;
H
NMR (CDCl , 400 MHz) δ 1.07 (s, 3H, –CH ), 1.12 (s, 3H, –CH ),
9,9-Dimethyl-12-phenyl-8,12-dihydro-9H-chromeno[3,2-e]
3
3
3
1
.34–1.38 (t, J=7.1 Hz, 3H, –OCH CH ), 2.17–2.28 (dd, J =16.3 Hz,
[1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (5a): Yield 65%; m.p.
2
3
6
1
8
–1
1
J =25.9 Hz, 2H, C –H), 2.49 (s, 2H, C –H), 4.36–4.41 (q, J=7.0 Hz,
188–190 °C. IR (KBr, ν, cm ): 2962, 2929, 2880, 1654; H NMR
(CDCl , 400 MHz) δ 1.12 (s, 3H, –CH ), 1.18 (s, 3H, –CH ), 2.27–2.37
2
4
2
1
H, –OCH CH ), 4.99 (s, 1H, C –H), 7.15–7.35 (m, 4H, Ph–H), 8.24 (s,
2
3
3
3
3
8
H, –N=CHOEt). Anal. calcd for C H ClN O : C, 65.54; H, 5.50; N,
(dd, J =16.5 Hz, J =23.2 Hz, 2H, C –H), 2.66–2.76 (dd, J =18.1 Hz,
1 2 1
J =24.1 Hz, 1H, C –H), 5.52 (s, 1H, C –H), 7.16–7.46 (m, 5H, Ph–H),
8.32 (s, 1H, C –H), 9.13 (s, 1H, C –H). Anal. calcd for C H N O : C,
20 18 4 2
21
21
2
3
10
12
7.28; found C, 65.43; H, 5.38; N, 7.41%.
2
5
2
3
-Amino-4-imino-8,8-dimethyl-5-phenyl-3,4,8,9-tetrahydro-
5
H-chromeno[2,3-d]pyrimidin-6(7H)-one (4a): Yield 61%; m.p.
69.35; H, 5.24; N, 16.17; found C, 69.45; H, 5.10; N, 16.27%.
12-(4-Methox yphenyl)-9,9- dimethyl- 8,12- dihydro-9H-
–1
1
214–216 °C. IR (KBr, ν, cm ): 3397, 3328, 3215, 2964, 1662; H NMR
(
CDCl , 400 MHz) δ 1.06 (s, 3H, –CH ), 1.13 (s, 3H, –CH ), 2.19–2.29
chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (5b):
3
3
3
9
7
–1
(dd, J =16.3 Hz, J =21.8 Hz, 2H, C –H), 2.48 (s, 2H, C –H), 4.43 (s,
Yield 72%; m.p. 208–210 °C. IR (KBr, ν, cm ): 3112, 2950, 2895, 1660;
1
2
5
2
1
1
H, C –H),4.56 (s, 2H, –NH ),7.22–7.33 (m, 6H, Ph+C –H). Anal.
H NMR (CDCl , 400 MHz) δ 1.12 (s, 3H, –CH ), 1.17 (s, 3H,–CH ),
2
3
3
3

4
84 JOURNAL OF CHEMICAL RESEARCH 2014
8
10
2
.27–2.37 (dd, J =16.3 Hz, J =22.5 Hz, 2H, C –H), 2.64–2.75 (dd,
2H, C –H), 3.75 (s, 3H, 12-OCH ), 3.86 (s, 3H, 2-OCH ), 5.26 (s, 1H,
3 3
1
2
10
12
J =17.7 Hz, J =22.7 Hz, 2H, C –H), 3.74 (s, 3H, 12-OCH ), 5.47 (s,
H, C –H), 6.79–6.81 (d, J=8.7 Hz, 2H, 12-(3′+5′)-H), 7.35–7.37 (d,
J=8.7 Hz, 2H, 12-(2′+6′)-H), 8.32 (s, 1H, C –H), 9.12 (s, 1H, C –H).
C –H), 6.80–6.82 (d, J=8.7 Hz, 2H, 12-(3′+5′)-H), 6.93–6.95 (d,
J=8.8 Hz, 2H, 2-(3′+5′)-H), 7.30–7.31 (m, 1H, 12-2′-H), 7.65–7.71
(m, 3H, 12-6′+2-(2′+6′)-H), 8.48 (s, 1H, C –H). Anal. calcd for
1
2
3
12
1
5
2
5
Anal. calcd for C H N O : C, 67.01; H, 5.36; N, 14.88; found C, 67.21;
C H N O : C, 69.70; H, 5.43; N, 11.61; found C, 69.83; H, 5.33; N,
21
20
4
3
28 26
4
4
H, 5.21; N, 14.74%.
2-(3,4-Dimethoxyphenyl)-9,9-dimethyl-8,12-dihydro-9H-
chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (5c):
11.56%.
1
2-(3,4-Dimethoxyphenyl)-12-(4-methoxyphenyl)-9,9-dimethyl-8,12-
dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-
one (6c): Yield 73%; m.p. 132–134 °C. IR (KBr, ν, cm ): 3118, 2952,
–1
–1
Yield 76%; m.p. 202–204 °C. IR (KBr, ν, cm ): 3083, 2967, 2837, 1656;
1
1
H NMR (CDCl , 400 MHz) δ 1.14 (s, 3H, –CH ), 1.18 (s, 3H,–CH ),
2892, 1659; H NMR (CDCl , 400 MHz) δ 1.00 (s, 3H, –CH ), 1.36 (s,
3
3
3
3
3
8
8
2
.29–2.38 (dd, J =16.3 Hz, J =20.2 Hz, 2H, C –H), 2.66–2.75 (t,
3H,–CH ), 2.21–2.32 (dd, J =16.4 Hz, J =26.2 Hz, 2H, C –H), 2.60 (s,
3 1 2
1
10
2
10
J=18.5 Hz, 2H, C –H), 3.78 (s, 3H, 12-OCH ), 3.88 (s, 3H, 12-OCH ),
5
(
2H, C –H), 3.74 (s, 3H, 12-OCH ), 3.94 (s, 3H, 2-OCH ), 4.05 (s, 3H,
3
3
3
3
12
12
.48 (s, 1H, C –H), 6.74–6.76 (d, J=8.3 Hz, 1H, 12-6′-H), 6.88–6.91
m, 1H, 12-5′-H), 7.09–7.10 (d, J=2.0 Hz, 1H, 12-2′-H), 8.33 (s, 1H,
2-OCH ), 5.44 (s, 1H, C –H), 6.78–6.80 (d, J=8.7 Hz, 2H, 12-(3′+5′)-
3
H), 6.88–6.90 (d, J=8.3 Hz, 1H, 2-5′-H), 7.10–7.12 (d, J=8.3 Hz, 1H,
12-2′-H), 7.30 (s, 1H, 12-6′-H), 7.52 (s, 1H, 2-2′-H), 7.63 (s, 1H, 2-6′-H),
5
2
C –H), 9.13 (s, 1H, C –H). Anal. calcd for C H N O : C, 65.01; H,
2
2
22
4
4
5.46; N, 13.78; found C, 65.34; H, 5.32; N, 13.65%.
8.45 (s, 1H, C
0.93; found C, 67.76; H, 5.61; N, 10.98%.
2-(3,4-Dimethoxyphenyl)-2-(4-methoxyphenyl)-9,9-dimethyl-8,12-
5
–H). Anal. calcd for C H N O : C, 67.96; H, 5.51; N,
29 28 4 5
9
,9-Dimethyl-12-(p-tolyl)-8,12-dihydro-9H-chromeno[3,2-e]
1
[
2
1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (5d): Yield 73%; m.p.
06–208 °C. IR (KBr, ν, cm ): 3063, 2957, 2932, 2873, 1662; H
1
–1
1
dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-
one (6d): Yield 72%; m.p. 118–120 °C. IR (KBr, ν, cm ): 3080, 2961,
2841, 1662; H NMR (CDCl , 400 MHz) δ 1.03 (s, 3H, –CH ), 1.15
(s, 3H, –CH ), 2.24–2.34 (dd, J =16.3 Hz, J =23.8 Hz, 2H, C –H),
NMR (CDCl , 400 MHz) δ 1.12 (s, 3H, –CH ), 1.18 (s, 3H,–CH ),
–1
3
3
3
2
.26 (s, 3H, 12-CH ), 2.27–2.37 (dd, J =16.2 Hz, J =23.3 Hz, 2H,
1
3
1
2
3
3
8
10
C –H), 2.65–2.75 (dd, J =17.7 Hz, J =23.1 Hz, 2H, C –H), 5.48 (s,
8
1
2
3
1
2
12
1H, C –H), 7.07–7.09 (d, J=7.9 Hz, 2H, 12-(3′+5′)-H), 7.33–7.35 (d,
10
2
6
.61 (s, 2H, C –H), 3.71 (s, 3H, 2-OCH ), 3.82–3.86 (d, J=16.0 Hz,
H, 2×12-OCH ), 5.41 (s, 1H, C –H), 6.75–6.77 (d, J=8.3 Hz, 1H,
3
5
2
J=8.1 Hz, 2H, 12-(2′+6′)-H), 8.32 (s, 1H, C –H), 9.12 (s, 1H, C –H).
12
3
Anal. calcd for C H N O : C, 69.57; H, 5.60; N, 15.43; found C, 69.29;
21
20
4
2
12-6′-H), 6.83–6.86 (m, 1H, 12-5′-H), 6.95–6.97 (d, J=8.8 Hz, 3H,
2-2′+2-(3′+5′)-H), 7.71–7.73 (d, J=8.6 Hz, 2H, 2-(2′+6′)-H), 8.48
H, 5.51; N, 15.27%. 12-(2,4-Dichlorophenyl)-9,9-dimethyl-8,12-
1
dihydro-9H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-
5
(s, 1H, C –H). Anal. calcd for C H N O : C, 67.96; H, 5.51; N, 10.93;
29 28 4 5
–1
one (5e): Yield 63%; m.p. 222–224 °C. IR (KBr, ν, cm ): 3056, 2958,
found C, 67.76; H, 5.65; N, 10.98%.
2,12-bis(3,4-Dimethoxyphenyl)-9,9-dimethyl-8,12-dihydro-9H-
chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (6e):
Yield 77%; m.p. 156–158 °C. IR (KBr, ν, cm ): 3073, 2972, 2841,
1
2
1
2
931, 2873, 1660; H NMR (CDCl , 400 MHz) δ 1.12 (s, 3H, –CH ),
3
3
8
.17 (s, 3H,–CH ), 2.25–2.36 (dd, J =16.4 Hz, J =25.6 Hz, 2H, C –H),
3
1
2
1
0
12
.67 (s, 2H, C –H), 5.74 (s, 1H, C –H), 7.22–7.24 (m, 1H, 12-6′-H),
–1
7
.28 (s, 1H, 12-5′-H), 7.54–7.56 (d, J=8.2 Hz, 1H, 12-3′-H), 8.30 (s, 1H,
1
1
658; H NMR (CDCl , 400 MHz) δ 1.02 (s, 3H, –CH ), 1.14 (s, 3H,
3
3
5
2
C –H), 9.16 (s, 1H, C –H). Anal. calcd for C H Cl N O : C, 57.84; H,
8
2
0
16
2
4
2
–CH ), 2.22–2.32 (dd, J =16.4 Hz, J =23.5 Hz, 2H, C –H), 2.60 (s,
3
1
2
3
.88; N, 13.49; found C, 57.69; H, 3.98; N, 13.61%.
,9-Dimethyl-12-(3-nitrophenyl)-8,12-dihydro-9H-chromeno[3,2-e]
1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (5f): Yield 63%; m.p.
10
2
H, C –H), 3.65 (s, 3H, 12-4′–OCH ), 3.80 (s, 3H, 12-3′–OCH ), 3.94
3 3
9
12
(s, 3H, 2-4′–OCH ), 4.08 (s, 3H, 2-3′–OCH ), 5.60 (s, 1H, C –H),
3
3
[
6
.72–6.75 (d, J=8.3 Hz, 1H, 12-6′-H), 6.81–6.84 (m, 1H, 12-5′-H),
–1
1
214–216 °C. IR (KBr, ν, cm ): 3052, 2963, 2927, 2868, 1662; H NMR
6
.88–6.90 (d, J=8.3 Hz, 1H, 12-2′-H), 6.95 (s, 1H, 2-5′-H), 7.55–7.62
(
CDCl , 400 MHz) δ 1.14 (s, 3H, –CH ), 1.19 (s, 3H,–CH ), 2.29–2.38
5
3
3
3
(d, J=24.5 Hz, 2H, 2-(2′+6′)-H), 8.43 (s, 1H, C –H). Anal. calcd for
8
(dd, J =16.4 Hz, J =30.6 Hz, 2H, C –H), 2.70–2.81 (dd, J =17.8 Hz,
1
2
1
C H N O : C, 66.41; H, 5.57; N, 10.33; found C, 66.65; H, 5.31; N,
10
12
30 30
4
6
J =38.1 Hz, 2H, C –H), 5.62 (s, 1H, C –H), 7.47–7.51 (t, J=7.9 Hz,
2
10.41%.
1
H, 12-5′-H), 7.97–7.98 (d, J=7.6 Hz, 1H, 12-6′-H), 8.04–8.06 (d,
2
-(4-Methoxyphenyl)-9,9-dimethyl-12-(p-tolyl)-8,12-dihydro-9H-
5
J=8.1 Hz, 1H, 12-4′-H), 8.17 (s, 1H, 12-2′-H), 8.31 (s, 1H, C –H), 9.17
chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (6f):
Yield 68%; m.p. 118–120 °C. IR (KBr, ν, cm ): 3058, 2963, 2930,
2
(s, 1H, C –H). Anal. calcd for C H N O : C, 61.38; H, 4.38; N, 17.89;
–1
2
0
17
5
4
found C, 61.45; H, 4.22; N, 17.73%.
2- (2- Chlorophe nyl)-9,9 - dime thyl- 8 ,12- dihydro -9H-
chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (5g):
1
2
3
3
869, 1660; H NMR (CDCl , 400 MHz) δ 1.01 (s, 3H, –CH ), 1.14 (s,
H, –CH ), 2.28 (m, 5H, 12-4′+C –H), 2.60 (s, 2H, C –H), 3.86 (s,
H, –OCH ), 5.24 (s, 1H, C –H), 6.93–6.95 (d, J=8.9 Hz, 2H, 12-
3
3
1
8
10
3
1
2
–1
3
Yield 66%; m.p. 238–240 °C. IR (KBr, ν, cm ): 3048, 2962, 2927,
(3′+5′)-H), 7.08–7.10 (d, J=7.9 Hz, 2H, 12-(2′+6′)-H), 7.26–7.28 (d,
1
2
(
2
869, 1672; H NMR (CDCl , 400 MHz) δ 1.12 (s, 3H, –CH ), 1.17
3
3
J=8.2 Hz, 2H, 2-(3′+5′)-H), 7.69–7.71 (d, J=8.7 Hz, 2H, 2-(2′+6′)-
H), 8.49 (s, 1H, C –H). Anal. calcd for C H N O : C, 72.09; H, 5.62;
8
s, 3H,–CH ), 2.26–2.34 (dd, J =16.4 Hz, J =28.4 Hz, 2H, C –H),
.63–2.71 (dd, J =18.0 Hz, J =20.1 Hz, 2H, C –H), 5.79 (s, 1H,
1 2
C –H), 7.13–7.16 (m, 1H, 12-6′-H), 7.24–7.26 (m, 2H, 12-(4′+5′)-H),
.60–7.61 (d, J=6.7 Hz, 1H, 12-3′-H), 8.29 (s, 1H, C –H), 9.14 (s, 1H,
3
1
2
5
10
28 26
4
3
N, 12.01; found C, 72.29; H, 5.56; N, 11.90%.
-(3,4-Dimethoxyphenyl)-9,9-dimethyl-12-(p-tolyl)-8,12-dihydro-
H-chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one
12
2
5
7
9
2
C –H). Anal. calcd for C H ClN O : C, 63.08; H, 4.50; N, 14.71; found
2
0
17
4
2
–1
(6g): Yield 73%; m.p. 214–216 °C. IR (KBr, ν, cm ): 3061, 2955, 2933,
C, 63.12; H, 4.44; N, 14.82%.
-(4-Methoxyphenyl)-9,9-dimethyl-12-phenyl-8,12-dihydro-9H-
chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (6a):
1
2
870, 1661; H NMR (CDCl , 400 MHz) δ 1.01 (s, 3H, –CH ), 1.14 (s,
3
3
2
8
10
3H, –CH ), 2.21–2.31 (m, 5H, 12-4′+C –H), 2.60 (s, 2H, C –H), 3.94
3
12
(s, 3H, –OCH ), 4.05 (s, 3H, –OCH ), 5.45 (s, 1H, C –H), 6.87–6.90
–1
3
3
Yield 70%; m.p. 208–210 °C. IR (KBr, ν, cm ): 3050, 2960, 2928,
(d, J=8.3 Hz, 1H, 2-5′-H), 7.06–7.27 (m, 5H, (12-Ph+2-2′)-H), 7.63 (s,
1
2
(
3
869, 1658; H NMR (CDCl , 400 MHz) δ 1.14 (s, 3H, –CH ), 1.27
3
3
5
1H, 2-6′-H), 8.45 (s, 1H, C –H). Anal. calcd for C H N O : C, 70.15;
8
10
29 28 4 4
s, 3H, –CH ), 2.31–2.41 (m, 2H, C –H), 2.67–2.73 (m, 1H, C –H),
3
H, 5.68; N, 11.28; found C, 70.34; H, 5.48; N, 11.31%.
10
12
.16–3.23 (m, 1H, C –H), 3.81 (s, 3H, –OCH ), 5.42 (s, 1H, C –H),
3
6
.82–6.96 (m, 2H, 2-(3′+5′)-H), 7.11–7.23 (m, 5H, Ph–H), 7.45–7.57
5
The research is supported by the National Natural Science
Foundation of China (Grant no. 21201087) and sponsored by
Qing Lan Project of Jiangsu Province.
(m, 2H, 2-(2′+6′)-H), 8.18 (s, 1H, C –H). Anal. calcd for C H N O :
2
7
24
4
3
C, 71.67; H, 5.35; N, 12.38; found C, 71.45; H, 5.43; N, 12.45%.
,12-bis(4-Methoxyphenyl)-9,9-dimethyl-8,12-dihydro-9H-
chromeno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-11(10H)-one (6b):
2
–1
Yield 75%; m.p. 136–138 °C. IR (KBr, ν, cm ): 3120, 2957, 2887,
Received 14 April 2014; accepted 27 June 2014
Paper 1402582 doi: 10.3184/174751914X14053476598397
Published online: 12 August 2014
1
1663; H NMR (CDCl , 400 MHz) δ 1.01 (s, 3H, –CH ), 1.13 (s, 3H,
3
3
8
–
CH ), 2.21–2.32 (dd, J =16.4 Hz, J =26.7 Hz, 2H, C –H), 2.60 (s,
3
1
2

JOURNAL OF CHEMICAL RESEARCH 2014 485
6
7
L.N. Dianova, T.G. Koksharova, N.V. Volkova, G.M. Anoshina, V.I.
Il’enko, G.G. Vatulina. Khim-Farm. Zh. 1992, 26, 30, Chem. Abstr., 1992,
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