Synthesis of some novel 3,6-bis(1,2,3-triazolyl)-s-triazolo[3,4-b]-1,3,4- thiadiazole derivatives

Article abstract of DOI:10.1002/jccs.200500015

The cyclization of 1-amino-2-mercapto-5-[1-(4-ethoxyphenyl)-5-methyl-1,2,3- triazol-4-yl]-1,3,4-triazole which was synthesized from p-ethoxyaniline with various triazole acid in absolute phosphorus oxychloride yields 3,6-bis(1,2,3-triazolyl)-s-triazolo[3,

Full text of DOI:10.1002/jccs.200500015

Journal of the Chinese Chemical Society, 2005, 52, 103-108
103
Synthesis of Some Novel
3,6-Bis(1,2,3-triazolyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole Derivatives
Heng-Shan Donga* (
) and Bin Wangb (
)
aState Key Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, College of Chemistry
and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, P. R. China
bCollege of Science and Engineering, Gansu Association University, Lanzhou, Gansu 730000, P. R. China
The cyclization of 1-amino-2-mercapto-5-[1-(4-ethoxyphenyl)-5-methyl-1,2,3-triazol-4-yl]-1,3,4-tri-
azole which was synthesized from p-ethoxyaniline with various triazole acid in absolute phosphorus
oxychloride yields 3,6-bis(1,2,3-triazolyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole derivatives 9a~j, and their
structures are established by MS, IR, CHN and 1H NMR spectral data.
Keywords: Synthesis; s-Triazolo[3,4-b]-1,3,4-thiadiazole; 1,2,3-Triazole; 1,3,4-Triazole;
3,6-Bis(1,2,3-triazolyl)-s-triazolo[3,4-b]-1,3,4-thiadiazole.
INTRODUCTION
In recent years in various publications, fused hetero-
triazole rings and one is a thiadiazole ring. The route of syn-
theses is in Scheme I.
cycles have been found to possess many unique properties in
synthesis and pharmacology. Especially, s-triazolo[3,4-b]-
1,3,4-thiadiazole derivatives have been attracting chemists
and pharmacologists. Certain compounds having a 1,3,4-tri-
azole nucleus have been reported as fungicidals,1 insecti-
cidals,2 antimicrobials3 and bactericidals.4 Compounds with
a 1,2,3-triazole nucleus have been reported as antibacterials,5
antifungals,6 antivirals,7 anti-inflammatories and analgesics.8
Recently, some new 1,3,4-triazole derivatives have been syn-
thesized as possible anticonvulsants9 and plant growth regu-
lators;10 and 1,2,3-triazole derivatives have been synthesized
to inhibit tumor proliferation, invasion, metastasis,11 and
have shown anti-HIV properties.12,13 Likewise, the 1,3,4-
thiadiazole nucleus which incorporates an N-C-S linkage ex-
hibits a large number of biological activities.14 The fused
s-triazolo[3,4-b]-1,3,4-thiadiazole derivatives show various
biological effects, such as antifungal,15 antibacterial, hy-
potensive, and CNS depressant activities.16 Phenacetin[N-
(4-Ethoxyphenyl)acetamide] is an antipyretic analgesic
which is included in our target compounds. For this reason,
the heterocyclic derivatives containing two 1,2,3-triazoles,
1,3,4-triazole, and 1,3,4-thiadiazole nucleus are very inter-
esting, and we also demonstrated that new the title com-
pounds of s-triazolo[3,4-b]-1,3,4-triazoles containing more
heterocycles can be studies, but their properties have not
been published in the literature up to now. There are six rings
in the complex structure of the compounds. Three rings are
EXPERIMENTAL SECTION
All melting points were uncorrected and determined on
an XT4-100x microscopic melting point apparatus. IR spectra
were obtained in KBr discs on a Shimadzu IR-435 spectrome-
ter. MS were performed on an HP-5988A spectrometer (EI at
70 eV). 1H NMR spectroscopy (CDCl3) were recorded on an
Avance Mercury plus-300 instrument with TMS as an inter-
nal standard. Elemental analyses were carried out on a Yanaco
CHN Corder MT-3 analyzer.
Phosphorus oxychloride was redistilled (b.p. 105).
2.1 5-Methyl-1-subsituted-1,2,3-triazol-4-caroxylic
acid (4a-j) were prepared following methods in the litera-
ture.17,18
2.2 Preparation of ethyl 1-(4-ethoxyphenyl)-5-methyl-
1,2,3-triazol-4-carboxyate (5)
In a 150 mL round bottomed flask was placed a mixture
of 4 (24.7 g, 0.10 mole), absolute ethanol (46 g, 59 mL, 1.0
mole) and concentrated sulfuric acid (6 mL), and the mixture
was refluxed gently for 12 hours, cooled to room tempera-
ture, and then refrigerated for 5 hours. A white solid was ob-
tained and filtered and the solid was washed with absolute
ethanol and recrystallized from absolute ethanol. The yield of
5 (a white crystalline solid, m.p. 113-114 °C) was 23.4 g
(85.0%). 1H NMR: 7.304-7.349 (d, 2H, J = 9.0 Hz, Ar1-3,5),
7.000-7.045 (d, 2H, J = 9.0 Hz, Ar1-2,6), 4.399-4.505 (q, 2H,

104 J. Chin. Chem. Soc., Vol. 52, No. 1, 2005
Dong and Wang
Ar1OCH2CH3). MS: 275 (
, 45), 247 (M-28-N2 or
Scheme I
CH2=CH2, 1), 230 (M-45-CH3CH2O, 10), 218 (M-57-N2-
CH3CH2, -17), 202 (M-CH3CH2OCO, 10), 190 (27), 174
(58), 146 (100), 121 (10), 83 (86), 65 (68). IR: 3411, 3091,
2983, 2935, 2884, 1717, 1593, 1563, 1516, 1435, 1375, 1349,
1248, 1222, 1120, 1103, 1049, 1023, 983, 837, 786 cm-1.
2.3 1-(4-Ethoxyphenyl)-5-methyl-1,2,3-triazol-4-car-
bonylhydrazine (6) was prepared from (5) following a proce-
dure in a method in the literature.19
N+2Cl-
NH2
N3
NaNO2,HCl
0~5oC
NaN3
OCH2CH3
1
OCH2CH3
3
OCH2CH3
2
COOH
CH3
A mixture of 0.1 mol compound 5 and 0.15 mole (85%
hydrazine hydrate) was refluxed in 200 mL of ethanol for 4
hours. A white solid was obtained and filtered. The solid was
recrystallized from dimethyl sulfoxide to gave 24.3 g (93.0%
yield) of product, m.p. 222-223 °C. 1H NMR: 7.477-7.521 (d,
2H, J = 8.8 Hz, Ar1-3,5), 7.095-7.139 (d, 2H, J = 8.8 Hz,
Ar1-2,6), 4.450-4.720 (broad peak, 3H, -NHNH2), 4.054-
4.157 (q, 2H, J = 7.0 Hz, Ar1OCH2-), 2.474 (s, 3H, TRZ1-
CH3), 1.315-1.385 (t, 3H, J = 7.0 Hz, Ar1OCH2CH3). MS: 261
COOEt
CH3
N
N
N
N
N
CH3COCH2CO2Et
EtONa,EtOH
EtOH
N
H2SO4
OCH2CH3
4
OCH2CH3
5
(
, 72), 217 (5), 204 (42), 202 (25), 174 (49), 162 (20), 146
CONHNHCSS-K+
CH3
CONHNH2
CH3
N
N
N
(86), 134 (15), 121 (16), 119 (21), 83 (31), 77 (25), 69 (50),
65 (66), 57 (77), 43 (100). IR: 3307, 3264, 3213 (N-H), 2979,
2931, 1669 (C=O), 1639, 1608, 1587, 1516, 1476, 1447,
1269, 1249 (Ar-O-R), 1119, 1045, 959 (1,2,3-triazole ring),
845, 658 cm-1.
N
N
N
H2NNH2 H2O
CS2,KOH
EtOH
OCH2CH3
OCH2CH3
2.4 1-Amino-5-[1-(4-ethoxyphenyl)-2-mercapto-5-
methyl-1,2,3-triazol-4-yl]-1,3,4-triazole (8) was prepared
from 6 via 7 following the method reported in the literature.20
Carbon disulfide (0.14 mol) was added dropwise to an
ice-cold solution of potassium hydroxide (0.15 mole) and
compound 6 (0.09 mole) in 150 mL absolute ethanol. The
mixture was stirred at room temperature for 15 hours. The
solid was filtered and washed with absolute diethyl ether (3 ´
50 mL). The product 7 was obtained in nearly quantitative
yield and employed in the next reaction without further puri-
fication.
6
7
N
N
N
N
N
SH
S
N
N
CH3
CH3
N
N
N
NH2
CH3
N
N
H NNH
2
2
4a~j
N
N
N
N
POCl
3
Ar
OCH2CH3
9a~j
OCH2CH3
8
A suspension of 7 (about 0.08 mol) and hydrazine hy-
drate 85% (0.16 mole) was refluxed while stirring for 4
hours. The color of the reaction mixture changed to dark
green, hydrogen sulfide was evolved, and a homogeneous so-
lution resulted. On dilution with 500 mL of cold water and
acidification with concentrated hydrochloric acid, a white
solid was precipitated. The product was filtered, washed with
water, and recrystallized from ethanol to give white flakes of
COOH
CH3
N
N
N+2Cl-
NH2
Ar
CH COCH CO Et
N
N3
Ar
3
2
2
NaNO ,HCl
2
NaN
3
Ar
EtONa,EtOH
o
Ar
0~5 C
4a~j
1
8, 17.8 g (70% yield), m.p. 204-205 °C. H NMR: 7.371-
J = 7.0 Hz, TRZ1CO2CH2-), 4.042-4.146 (q, 2H, J = 6.8 Hz,
Ar1OCH2-), 2.540 (s, 3H, TRZ1-CH3), 1.417-1.487 (t, 3H, J =
7.0 Hz, TRZ1CO2CH2CH3), 1.402-1.472 (t, 3H, J = 6.8 Hz,
7.400 (d, 2H, J = 8.7 Hz, Ar1-3,5), 7.047-7.076 (d, 2H, J = 8.7
Hz, Ar1-2,6), 4.080-4.150 (q, 2H, J = 7.0 Hz, Ar1-OCH2-),
2.525 (s, 3H, TRZ1-CH3), 2.521 (s, 1H, -SH), 1.620-1.840

3,6-Bistriazolyl-triazolo[3,4-b]thiadiazoles
J. Chin. Chem. Soc., Vol. 52, No. 1, 2005 105
Table 1. Structures and melting points of the compounds 4a-j
Compound No.
Ar.
Mp (°C) Compound No.
Ar
Mp (°C)
4a
4b
4c
4d
4e
4-CH3C6H4
3-ClC6H4
4-ClC6H4
4-BrC6H4
3-BrC6H4
183-184
186-188
177-179
204-205
181-182
4f
4g
4h
4i
2,5-Cl2C6H3
4-CH3OC6H4
4-C2H5OC6H4
a-C10H7
154-156
185-186
166-167
184-186
184-185
4j
b-C10H7
Table 2. Structures, yields and melting points of compounds 9a-j
Compound
R
Yield (%) M.P (°C) Compound
R
Yield (%) M.P (°C)
9a
9b
9c
9d
9e
4-CH3C6H4
3-ClC6H4
4-ClC6H4
4-BrC6H4
3-BrC6H4
65
76
72
66
74
242-243
228-229
289-290
290-291
227-228
9f
9g
9h
9i
2,5-Cl2C6H3
4-CH3OC6H4
4-C2H5OC6H4
a-C10H7
70
70
72
45
48
252-253
236-237
226-227
267-268
286-287
9j
b-C10H7
a Satisfactory microanalyses were obtained for all the compounds.
Table 3. IR spectral data of compounds 9a-j
No.
IR (cm-1) (KBr disc)
9a 3081, 2976, 2893, 1610, 1517, 1471, 1251, 1175, 1118, 1045, 966, 946, 840, 823, 781, 717
9b 3069, 2980, 2935, 2883, 1611, 1589, 1518, 1490, 1466, 1302, 1254, 1172, 1114, 1044, 969,
948, 846, 790, 721, 686
9c 3076, 2974, 2930, 2893, 1608, 1515, 1470, 1410, 1249, 1174, 1115, 1092, 1042, 966, 944, 837,
782, 715, 671
9d 3093, 2976, 2893, 1608, 1516, 1495, 1473, 1400, 1272, 1249, 1176, 1113, 1075, 1044, 966,
946, 840, 783, 714, 671
9e 3078, 2979, 2933, 2882, 1610, 1587, 1518, 1488, 1466, 1302, 1255, 1171, 1114, 1044, 970,
948, 845, 787, 757, 720, 686
9f 3091, 2980, 2930, 1614, 1587, 1519, 1472, 1254, 1174, 1095, 1048, 967, 947, 838, 808, 781,
721
9g 3082, 2977, 2837, 1610, 1517, 1471, 1252, 1175, 1117, 1042, 966, 945, 838, 780, 718
9h 3067, 2981, 2920, 1608, 1584, 1516, 1462, 1303, 1255, 1172, 1115, 1045, 967, 947, 843, 782,
721
9i 3056, 2977, 2935, 2895, 1610, 1518, 1469, 1303, 1252, 1174, 1118, 1049, 969, 948, 845, 804,
775, 720
9j 3056, 2976, 2882, 1608, 1517, 1472, 1416, 1248, 1174, 1114, 1050, 970, 947, 828, 780, 750,
719
(broad peak, 2H, -NH2), 1.449-1.497 (t, 3H, J = 7.0 Hz,
atives 9a-j.
A mixture of 1-amino-5-[1-(4-ethoxyphenyl)-5-meth-
Ar1-OCH2CH3). MS: 317 ( , 16), 302 (1), 285 (1), 273 (3),
260 (5), 201 (3), 194 (17), 179 (8), 173 (3), 171 (11), 151
(11), 137 (13), 121 (100), 111 (7), 105 (23), 95 (10), 83 (10),
77 (17), 69 (16), 57 (16), 55 (20), 43 (19). IR: 3449, 3281
(N-H), 3186, 3111, 2974, 2942, 2838, 2783 (S-H), 1632,
1610 (C=N), 1519, 1499, 1467, 1291, 1254 (Ar-O-R), 1174,
1019, 949 (1,2,3-triazole ring), 840, 669.
yl-1,2,3-triazol-4-yl]-2-mercapto-1,3,4-triazole 8 (1 mmol),
5-methyl-1-substituted-1,2,3-triazol-4-carboxylic acid (1
mmol), and POCl3 (5 mL) was heated under refluxing for 6
hours with stirring. The cooled reaction mixture was poured
into crushed ice and made alkaline by adding potassium hy-
droxide, and then the resulting solid was filtered and dried.
The solid was purified by chromatography on a column of
silica gel and eluted successively with 2:1 ethyl acetate-
petroleum ether. The desired product was obtained and its re-
2.5 General procedure of preparation of 6-(1-aryl-5-
methyl-1,2,3-triazol-4-yl)-3-[1-(4-ethoxyphenyl)-5-methyl-
1,2,3-triazol-4-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazole deriv-

106 J. Chin. Chem. Soc., Vol. 52, No. 1, 2005
Table 4. 1H NMR spectral data of compounds 9a-j
Dong and Wang
No.
1H NMR (CDCl3-d) d (ppm), J (Hz)
9a
7.436-7.465 (d, 2H, J = 8.7 Hz, Ar2-3,5), 7.431-7.461 (d, 2H, J = 9.0 Hz, Ar1-3,5), 7.062-7.091 (d, 2H, J = 8.7
Hz, Ar2-2,6), 7.058-7.088 (d, 2H, J = 9.0 Hz, Ar1-2,6), 4.115-4.143 (q, 2H, J = 7.2 Hz, Ar1OCH2), 2.787 (s,
3H, TRZ2-CH3), 2.740 (s, 3H, TRZ1-CH3), 1.457-1.505 (t, 3H, J = 7.2 Hz, Ar1OCH2CH3)
7.441-7.598 (m, 3H, Ar2-4,5,6), 7.433-7.463 (d, 2H, J = 9.0 Hz, Ar1-3,5), 7.266 (s, 1H, Ar2-2), 7.060-7.090 (d,
2H, J = 9.0 Hz, Ar1-2,6), 4.091-4.163 (q, 2H, J = 7.2Hz, Ar1OCH2-), 2.834 (s, 3H, TRZ2-CH3), 2.742 (s, 3H,
TRZ1-CH3), 1.457-1.505 (t, 3H, J = 7.2 Hz, Ar1OCH2CH3)
7.590-7.619 (d, 2H, J = 8.7 Hz, Ar2-3,5), 7.462-7.492 (d, 2H, J = 9.0 Hz, Ar1-3,5), 7.463-7.492 (d, 2H, J = 8.7
Hz, Ar2-2,6), 7.044-7.074 (d, 2H, J = 9.0 Hz, Ar1-2,6), 4.076-4.147 (q, 2H, J = 7.2 Hz, Ar1OCH2-), 2.818 (s,
3H, TRZ2-CH3), 2.740 (s, 3H, TRZ1-CH3), 1.443-1.491 (t, 3H, J = 7.2 Hz, Ar1OCH2CH3)
7.760-7.787 (d, 2H, J = 8.1 Hz, Ar2-3,5), 7.429-7.461 (d, 2H, J = 9.6 Hz, Ar1-3,5), 7.409-7.436 (d, 2H, J = 8.1
Hz, Ar2-2,6), 7.058-7.090 (d, 2H, J = 9.6 Hz, Ar1-2,6), 4.091-4.163 (q, 2H, J = 7.2 Hz, Ar1-OCH2-), 2.816 (s,
3H, TRZ2-CH3), 2.742 (s, 3H, TRZ1-CH3), 1.457-1.505 (t, 3H, J = 7.2 Hz, Ar1-CH2CH3)
7.480-7.740 (m, 3H, Ar2-4,5,6), 7.428-7.460 (d, 2H, J = 9.6 Hz, Ar1-3,5), 7.259 (s, 1H, Ar2-2), 7.054-7.086 (d,
2H, J = 9.6 Hz, Ar1-2,6), 4.111-4.139 (q, 2H, J = 7.2 Hz, Ar1OCH2-), 2.827 (s, 3H, TRZ2-CH3), 2.724 (s, 3H,
TRZ1-CH3), 1.453-1.501 (t, 3H, J = 7.2 Hz, Ar1OCH2CH3)
9b
9c
9d
9e
9f
7.549-7.611 (d, 2H, J = 7 Hz, Ar2-3,4), 7.432-7.463 (d, 2H, J = 9.3 Hz, Ar1-3,5), 7.271 (s, 1H, Ar1-6), 7.059-
7.090 (d, 2H, J = 9.3 Hz, Ar1-2,6), 4.093-4.161 (q, 2H, J = 7.2 Hz, Ar1OCH2-), 2.782 (s, 3H, TRZ2-CH3),
2.742 (s, 3H, TRZ1-CH3), 1.461-1.505 (t, 3H, J = 7.2 Hz, Ar1OCH2CH3)
9g
7.434-7.461 (d, 2H, J = 8.1 Hz, Ar2-3,5), 7.414-7.444 (d, 2H, J = 9.0 Hz, Ar1-3,5), 7.092-7.119 (d, 2H, J = 8.1
Hz, Ar2-2,6), 7.060-7.090 (d, 2H, J = 9.0 Hz, Ar1-2,6), 4.093-4.162 (q, 2H, J = 7.2 Hz, Ar1O-CH2-), 3.914 (s,
3H, Ar2OCH3), 2.771 (s, 3H, TRZ2-CH3), 2.740 (s, 3H, TRZ1-CH3), 1.461-1.505 (t, 3H, J = 7.2 Hz,
Ar1OCH2CH3)
9h
9i
7.375-7.463 (2d, 4H, J = 8.1 Hz, Ar1, Ar2-2,6), 7.046-7.097 (d, 4H, J = 8.1 Hz, Ar1, Ar2-3,5), 4.082-4.152 (2q,
4H, J = 7.2 Hz, Ar1, Ar2-OCH2-), 2.726, 2.755 (2s, 6H, Ar1, Ar2-CH3), 1.448-1.495 (t, 6H, J = 7.2 Hz, Ar1,
Ar2-OCCH3)
8.014-8.154 (dd, 2H, J = 8.1 Hz, Ar2-2,4), 7.558-7.680 (m, 4H, Ar2-5,6,7,8), 7.414-7.443 (d, 2H, J = 8.7 Hz,
Ar2-3,5), 7.416-7.443 (d, 1H, J = 8.1 Hz, Ar2-3), 7.043-7.072 (d, 2H, J = 8.7 Hz, Ar1-2,6), 4.077-4.146 (q, 2H,
J = 6.9 Hz, Ar1OCH2-), 2.739 (S, 3H, TRZ1-CH3), 2.612 (S, 3H, TRZ2-CH3), 1.445-1.491 (t, 3H, J = 6.9 Hz,
Ar1OCH2CH3)
9j
8.016-8.106 (m, 4H, Ar2), 7.534-7.674 (m, 3H, Ar2), 7.414-7.437 (d, 2H, J = 7.2 Hz, Ar1 = 3.5), 7.058-7.082
(d, 2H, J = 7.2 Hz, Ar1-2.6), 4.081-4.157 (q, 2H, J = 7.2 Hz, Ar1OCH2-), 2.865 (S, 3H, TRZ2-CH3), 2.741 (S,
3H, TRZ1-CH3), 1.449-1.501 (t, 3H, J = 7.2 Hz, Ar1OCH2CH3)
sults are given in Table 2.
compound 9 shows absorption peaks for N-N=C in the region
of 1248-1255 cm-1 and for C=N in 1608-1614 cm-1.21 The typ-
ical vibration bands of N-N=N were in the region of 966-970,
944-948 cm-1 (The typical vibration bands of N-N=N in 1H-
1,2,3-triazole ring are the values but 2H-triazole is not),22
which shows two 1,2,3-triazoles rings in one molecule. The
vibration bands of N-N=N are in agreement with the values
reported for triazole (N-N=N absorptions in the region 950-
1120 cm-1) by Ykman and Hartzel.23,24 Compounds 9a-j show
absorption peaks for C-S-C in the region of 714-721 cm-1.21
In the mass spectra of 9a-j the molecular ion peaks are very
weak (relative intensities ~1-4%) and all the members of 9a-j
exhibit some important ion peaks which are identified. The
chemical shift of the triazole ring methyl group shows in the
range of d 2.724-2.865 ppm in compounds 9a-j, whereas the
chemical shift of the triazole ring methyl group shows in the
range of d 2.525 ppm in compound 8. The chemical shift of
RESULTS AND DISCUSSION
The new 3-[1-(4-ethoxyphenyl)-5-methyl-1,2,3-tri-
azol-4-yl]-6-substituted-s-triazolo[3,4-b]-1,3,4-thiadiazole
9a-j have been synthesized by the condensation of 1-ami-
no-2-mercappto-5-[1-(4-ethoxyphenyl)-5-metyl-1,2,3-trizol-
4-yl]-1,3,4-triazole 8 with various 5-methyl-1-substituted-
1,2,3-triazol-4-carboxylic acid 4a-j in the presence of phos-
phorus oxychloride. The structure of these compounds was
characterized with 1H NMR, IR, and MS spectroscopy. The
results are given in Tables 2, 3, 4 and 5. IR absorption peaks
of 8 at 3281 cm-1 and 3186 cm-1 are assigned to its NH2 and
2782 cm-1 is assigned to its SH group. When 8 converted 9,
the SH peak and NH2 peak disappears. Like the allied system,

3,6-Bistriazolyl-triazolo[3,4-b]thiadiazoles
J. Chin. Chem. Soc., Vol. 52, No. 1, 2005 107
Table 5. MS data of compounds 9a-j
.
No.
m/z (%)
9a 498 ( , 1), 470 (38), 441 (20), 243 (7), 200 (10), 171 (49), 111 (28), 97 (50), 83 (71), 71 (60), 57 (86), 43
(73)
9b 518 ( , 1), 490 (31), 461 (15), 433 (6), 243 (6), 204 (13), 190 (24), 171 (39), 164 (29), 111 (59), 97 (58), 83
(62), 71 (73), 57 (100), 43 (74)
9c 518 ( , 1), 490 (45), 461 (15), 251 (66), 221 (44), 204 (27), 189 (40), 171 (90), 165 (55), 147 (46), 135 (75),
129 (70), 111 (8), 97 (9), 83 (12), 71 (23), 57 (27), 43 (100)
9d 562 ( , 2), 534 (11), 505 (8), 398 (4), 236 (12), 198 (10), 171 (29), 155 (31), 111 (41), 97 (66), 83 (70), 71
(79), 57 (100), 43 (71)
9e 562 ( , 2), 534 (62), 505 (32), 398 (12), 234 (31), 171 (100), 155 (70), 119 (18), 102 (19), 76 (42), 65 (45),
57 (6), 51 (17), 43 (11)
9f 552 ( , 2), 524 (32), 495 (11), 467 (15), 238 (23), 200 (33), 171 (100), 111 (8), 97 (40), 83 (49), 71 (39), 57
(47), 43 (47)
9g 514 ( , 2), 486 (87), 457 (34), 416 (8), 243 (12), 200 (26), 186 (74), 171 (75), 160 (21), 148 (22), 119 (15),
97 (21), 83 (38), 77 (48), 57 (52), 43 (100)
9h 528 ( , 2), 500 (57), 471 (25), 200 (39), 172 (100), 146 (31), 111 (27), 97 (50), 83 (58), 77 (27), 71 (56), 57
(75), 43 (70)
9i
534 ( , 4), 506 (44), 477 (12), 262 (21), 206 (65), 183 (35), 171 (46), 127 (6), 119 (3), 97 (7), 83 (10), 77
(11), 69 (15), 57 (18), 43 (37)
9j 534 ( , 3), 506 (60), 477 (22), 262 (8), 206 (92), 183 (22), 171 (55), 127 (17), 119 (4), 97 (11), 83 (14), 77
(16), 69 (24), 57 (31), 43 (47)
(Chem. Abstr. 1979, 91, 175361z).
the triazole ring Me-proton is in agreement with the values
reported for triazole (Typical chemical shift of the triazole
ring Me-proton is at about d 2.45 ppm in the NMR spectra) by
Ykman.25 Recently, we have established the crystal structure
of 9h by X-ray diffraction. The crystal structure of 9h con-
forms to the structure (Scheme I).
5. Zhang, Z.-Y.; Liu, Y.; Yang, S.-Y. Pharmaceutica Sinica
1991, 26(11), 809.
6. Abdou, N. A.; Soliman, S. N.; Abou Sier, A. H. Bull Fac
Pharm. 1990, 28(2), 29.
7. Srivastava, A. J.; Swarup, S.; Saxena, V. K.; Chowdhury, B.
L. J. Indian Chem. Soc. 1991, 68(2), 103.
8. Cooper, K.; Steele, J.; Richardson, K. EP 329357. (Chem.
Abstr. 1990, 112, 76957u).
ACKNOWLEDGEMENTS
9. Husain, M. I.; Mohd, A. J. Indian Chem. Soc. 1986, 63, 317.
10. Elliott, R.; Sunley, R. L.; Griffin, D. A. GB 2,175,301.
(Chem. Abstr. 1987, 107, 134310n).
The authors wish to acknowledge that this project is
supported by NNSFC (chuangxin qunti, 2002-001) and Lan-
zhou University NLAOC.
11. Kohn, E. C.; Liotta, L. A. U.S. 637145 (Chem. Abstr. 1991,
115, 248099w).
12. Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; De
Clercq, E.; Perno, C. F.; Karlsson, A.; Balzarini, J.;
Camarasa, M. J. J. Med. Chem. 1994, 37, 4185.
13. De Clercq, E. Medicinal Research Reviews 2002, 22(6), 531.
14. Omar, A.; Mohsen, M. E.; AboulWafa, O. M. J. Heterocycl.
Chem. 1986, 23, 1339.
Received December 15, 2003.
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