The synthesis of (4E)-N-(4-chlorophenyl)-5-substituted-2-diazo-3-oxopent-4- enoic acid amides

Article abstract of DOI:10.1002/jccs.200500141

The (4E)-N-(4-chlorophenyl)-5-(3-chlorophenyl)-2-diazo-3-oxopent-4-enoic acid amides 5a～j were synthesized with N-(4-chlorophenyl)-2-diazo-3- oxobutyramide 4 from p-chloroaniline and various arylaldehydes. The yielded products 5a～j were investigated with NMR, MS, IR, and X-ray crystal lo graphic techniques.

Full text of DOI:10.1002/jccs.200500141

Journal of the Chinese Chemical Society, 2005, 52, 1011-1016
1011
The Synthesis of (4E)-N-(4-chlorophenyl)-5-substituted-2-diazo-3-
oxopent-4-enoic Acid Amides
Heng-Shan Dong* (
State Key Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, College of Chemistry and
), Dong-Dong Wang (
) and Chi-Qiong Jin (
)
Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, P. R. China
The (4E)-N-(4-chlorophenyl)-5-(3-chlorophenyl)-2-diazo-3-oxopent-4-enoic acid amides 5a~j were
synthesized with N-(4-chlorophenyl)-2-diazo-3-oxobutyramide 4 from p-chloroaniline and various arylal-
dehydes. The yielded products 5a~j were investigated with NMR, MS, IR, and X-ray crystallographic tech-
niques.
Keywords: a-Diazodicarbonyl compound; 2-Diazo-3-oxopent-4-enoic acid amide; Synthesis;
Ethyl(acetoketal)acetate; (2-Methyl-[1,3]dioxolan-2-yl)-acetic acid ethyl ester.
INTRODUCTION
azo-3-oxopent-4-enoic acid amides.
In this paper, we report the synthesis of (4E)-N-(4-
chlorophenyl)-5-substituted-2-diazo-3-oxopent-4-enoic acid
amides 5a~j. The route of synthesis is in Scheme I.
In recent years in various publications, certain com-
pounds having a 1,2,3-triazole nucleus have been reported as
antibacterials,1 antifungals,2 antivirals,3 anti-inflammatories,
and analgesics.4 Recently, some new 1,3,4-triazole deriva-
tives have been synthesized as possible anticonvulsants5 and
plant growth regulators;6 1,2,3-triazole derivatives have been
synthesized to inhibit tumor proliferation, invasion, metasta-
sis,7 and have shown anti-HIV activity.8-13 Likewise, pyrone
nucleus derivatives have been synthesized which have shown
anti-HIV activity.14-19 We have reported the crystalline
structure of 5-[5-amino-1-(4-chlorophenyl)-1,2,3-triazol-
4-yl]-2-(3-bromoanilino)-1,3,4-thiodiazole and their deriv-
atives,20-22 and the crystalline structure of 3-[5-methyl-1-(4-
methylphenyl)-1,2,3-triazol-4-yl]-s-triazolo[3,4-b]-1,3,4-
thiadiazole.23 We figure the synthesis of 4-acetyl-1-(p-chlo-
rophenyl)-5-hydroxyl-1,2,3-triazole by reaction of p-chloro-
phenyl azide with ethyl(acetoketal)acetate or (2-methyl-
[1,3]-dioxolan-2-yl)-acetic acid ethyl ester, N-(4-chloro-
phenyl)-2-diazo-3-oxobutyramide is gotten by the triazole
ring opening in the medium of acid water, subsequently react-
ing the compound with arylaldehydes. We obtained (4E)-N-
(4-chlorophenyl)-5-substituted-2-diazo-3-oxopent-4-enoic
acid amide. A great deal of interest has been focused on the
a-diazocarbonyl compounds.24 When properly substituted,
they can be useful materials for photoresist. This has inspired
us to extend our work on a-diazodicarbonyl compounds N-
(4-chlorophenyl)-2-diazo-3-oxo-butyramide with heterocy-
clic openings in order to study the synthesis and potential ap-
plications of (4E)-N-(4-chlorophenyl)-5-substituted-2-di-
Scheme I
5a Ar=ph; 5b, 3-chlorophenyl; 5c, 3,4-dimethoxyphenyl; 5d,
3,4-methylenedioxyphenyl; 5e, 4-methoxyphenyl; 5f 2-fur-
anyl; 5g, 4-N,N-dimethylaminophenyl; 5h, 4-hydroxyphenyl;
5i, 2-hydroxyphenyl; 5j, 4-hydroxy-3-methoxyphenyl.

1012 J. Chin. Chem. Soc., Vol. 52, No. 5, 2005
Dong et al.
EXPERIMENTAL SECTION
hydroxide (0.8 g) in 10 mL water and 10 mL ethanol, then
various arylaldehydes were dropped into the solution during
continuous stirring at room temperature. The reaction mix-
ture was stirred at room temperature for 8 h and acidified to
pH = 7~8 with HCl (4 M), filtered and recrystalized from eth-
anol to give 5a~j.
Melting points were uncorrected and determined on an
XT4-100x microscopic melting point apparatus. IR spectra
were obtained in KBr discs on a Nicolet 170SX FT-IR spec-
trometer. 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
internal standard. Un spectra were obtained on a Shimadzu
Un-260 spectrometer.
Compound 5b. Un (CHCl3, c = 10-3 mol/L), l = 280.4
nm (1.010), l = 241.8 nm (0.957).
Compound 6. Yield (methods A 56%, methods B 20%),
mp 177-178 °C, IR umax: 3111 (Ar-H), 3027, 2916, (w, CH3),
1670, 1688 (s, C=O), 1651, 1548, 1485 (s, Ar), 1216, 1070
1
(2-Methyl-[1,3]-dioxolan-2-yl)-acetic acid ethyl ester 1 was
prepared following a method reported in the literature25
(C-O-CH3), 955, 830 (m, Ph-1,2H), 728 (C-Cl) cm-1. H
NMR d : 7.936-7.967 (d, 2H, J = 9.3 Hz, Ph-2,6H); 7.443-
H
Compound 1 (in 90% yield). 1H NMR d : 4.039-4.164
7.474 (d, 2H, J = 9.3 Hz, Ph-3,5H); 4.311 (s, 3H, CH3O-),
H
+
·
(q, 2H, J = 7.2 Hz, OCH2CH3); 3.933 (s, 4H, -OCH2CH2O-);
2.616 (s, 2H, -CCH2CO2-); 1.455 (s, 3H, CH3-); 1.185-1.256
(t, 3H, J = 7.2 Hz, CH2-CH3) ppm.
2.609 (s, 3H, CH3-) ppm. MS m/z: 251 (M , 21), 253 (M+2,
7), 236 (1), 194 (4), 141 (4), 139 (14), 113 (22), 111 (76), 84
(16), 75 (24), 69 (3), 63 (3), 55 (1), 50 (10), 43 (100), 42 (67).
Un (CHCl3, c = 10-3 mol/L), l = 324.6 nm (1.271), l = 240.0
nm (0.510).
N-(4-chlorophenyl)-2-diazo-3-oxo-butyramide was pre-
pared from p-chloroaniline following a method reported
in the literature26
The solution of sodium ethoxide [3.5 g (1.5 mol) of so-
dium in 50 mL of ethanol] was added to a solution of 15.3 g
(0.1 mol) p-chlorophenyl azide and 12.0 mL (0.1 mol) ethyl
(acetoketal)acetate 1 in 80 mL absolute ethanol in one por-
tion under an ice bath. Then the reaction mixture was heated
under reflux for 48 hours. The solution was cooled to room
temperature and the solvent was removed in vacuo to give a
syrup mixture. This mixture was dissolved in 100 mL water
and acidified to pH = 1~2 with hydrochloric acid (4 M). After
stirring in an ice bath for one hour the resulting precipitate
was filtered off and washed with water and recrystalized from
ethanol to give 16 g of compound 4. Yield 65%, mp 145-146
°C (Lit. 143 °C),27 IR umax: 3236, (b, -N-H), 3069 (Ar-H),
3027, 2938, (w, CH3), 2125 (s, diazo), 1670, 1638 (s, C=O,
RESULTS AND DISCUSSION
The crystal structure of the title compound 5b is shown
in Fig. 1. In recent years the synthesis and characteristics of
5-amino-1-(4-chlorophenyl)-1,2,3-triazol-4-yl and 5-methyl-
1-(4-methylphenyl)-1,2,3-triazol-4-yl derivatives have been
investigated. These heterocyclic compounds contain a 1,2,3-
triazole ring, and they are a series stable compounds.20-23 In
order to continue our earlier studies, we synthesized com-
pounds 5a~j.
We isolated the compound 4 that was an open ring prod-
uct from 4-acetyl-1-(4-chlorophenyl)-5-hydroxy-1,2,3-tri-
azole. We claim that the reaction mechanism is the following
formation under the reaction conditions in Scheme II. It is in
-CONH-), 1596, 1548, 1488 (s, Ar), 953, 841, 820 (m, Ph-
1
1,2H), 722 (C-Cl) cm-1. H NMR d : 10.216 (b, 1H, NH);
H
Table 1. Structures, yields and melting points of compounds 5a~j
7.521-7.545 (d, 2H, J = 7.2 Hz, Ph-2,6H); 7.296-7.271 (d,
No
Ar
M.p. (°C) Yield (%)
2H, J = 7.2 Hz, Ph-3,5H); 2.425 (s, 3H, CH3-) ppm. MS m/z:
+
·
237(M , 21), 239 (M+2, 7), 194 (4), 181 (9), 167 (10), 153
5a
5b
5c
5d
5e
5f
5g
5h
5i
phenyl
3-chlorophenyl
3,4-dimethoxyphenyl
3,4-methylenedioxyphenyl
4-methoxyphenyl
2-furanyl
4-N,N-dimethylaminophenyl
4-hydroxyphenyl
2-hydroxyphenyl
4-hydroxy-3-methoxyphenyl
170-171
159-160
169-170
187-188
188-189
154-156
199-200
190-192
194-196
194-195
80
87
50
63
83
75
60
62
60
50
(6), 138 (54), 127 (14), 111 (28), 99 (21), 83 (44), 75 (28), 69
(5), 63 (19), 55 (14), 50 (11), 43 (100), 39 (10). Un (CHCl3, c
= 10-3 mol/L), l = 258.4 nm (1.729).
(4E)-N-(4-chlorophenyl)-5-substituted-2-diazo-3-oxopent-
4-enoic acid amides 5a~j were prepared following the
method
5j
1.5 g of compound 4 was added to a solution of sodium

Substituted-2-diazo-3-oxopent-4-enoic Acid Amides
J. Chin. Chem. Soc., Vol. 52, No. 5, 2005 1013
Table 2. IR spectral data for compounds 5a-j
Table 3. 1H NMR spectral data for compounds
No
IR (cm-1) (KBr disc)
No
1H NMR (CDCl3-d) d (ppm), J (Hz)
10.669 (b, 1H, NH), 7.836-7.887 (d, 1H, J = 15 Hz,
5a 3237 (b, -N-H), 3188, 3112 (Ar-H), 3060, 3029 (w, CH3),
2122 (s, diazo), 1671, 1642 (s, C=O, -CONH-), 1580,
1545, 1488 (s, Ar), 977, 821 (m, Ph-1,2H), 836, 756 (m),
687 (C-Cl).
5b 3224 (b, -N-H), 3179, 3110 (Ar-H), 3060, 2938 (w, CH3),
2120 (s, diazo), 1668, 1641 (s, C=O, -CONH-), 1576,
1543, 1490 (s, Ar), 975, 830 (m, Ph-1,2H), 925, 789, 789
(m, 3-chlorophyl 1H or 3H), 738, 692 (C-Cl).
5c 3234 (b, -N-H), 3183, 3116 (Ar-H), 3067, 2936 (w, CH3),
2116 (s, diazo), 1676, 1634 (s, C=O, -CONH-), 1571,
1542, 1508 (s, Ar), 1266, 1242, 1019 (s, Ar-O-CH3), 966,
831 (m, Ph-1,2H), 801, 717 (m), 736 (C-Cl).
5d 3225 (b, -N-H), 3180, 3108 (Ar-H), 3058, 2978, 2904 (w,
CH3), 2117 (s, diazo), 1670, 1635 (s, C=O, -CONH-),
1569, 1542, 1488 (s, Ar), 1253, 1238, 1037, 1018 (s, Ar-O-
CH3), 973, 833 (m, Ph-1,2H), 805, 718 (m), 739 (C-Cl).
5e 3225 (b, -N-H), 3177, 3108 (Ar-H), 3061, 2939 (w, CH3),
2116 (s, diazo), 1672, 1633 (s, C=O, -CONH-), 1605,
1569, 1541, 1511 (s, Ar), 1265, 1237, 1023 (s, Ar-O-CH3),
982, 823 (m, Ph-1,2H), 714 (C-Cl).
5f 3234 (b, -N-H), 3182, 3110 (Ar-H), 3063, 2904 (w, CH3),
2123 (s, diazo), 1672, 1637 (s, C=O, -CONH-), 1572,
1542, 1490 (s, Ar), 1267, 1243, 1011 (s, Furanyl), 966, 821
(m, Ph-1,2H), 754 (m), 731 (C-Cl).
5g 3226 (b, -N-H), 3175, 3108 (Ar-H), 3063, 2896, 2821 (w,
CH3), 2118 (s, diazo), 1670, 1612 (s, C=O, -CONH-),
1524, 1435 (s, Ar), 1240, 1171, 1023, 1001 (s, Ar-N-CH3),
974, 836, 804 (m, Ph-1,2H), 741(C-Cl).
5h 3393 (ms, b, -OH and -N-H), 2922 (w, CH3), 2114 (m,
diazo), 1607 (s, b, C=O, -CONH-), 1493 (s, Ar), 1254,
1070 (s, Ar-OH), 966, 836 (m, Ph-1,2H), 718 (C-Cl).
5i 3386 (ms, b, -OH and -N-H), 2919 (w, CH3), 2126 (m,
diazo), 1604 (s, b, C=O, -CONH-), 1494 (s, Ar), 1239,
1069 (s, Ar-OH), 966, 814, 754 (m, Ph-1,2H), 718 (C-Cl).
5j 3402 (ms, b, -OH and -N-H), 2923 (w, CH3), 2121 (m,
diazo), 1603 (s, b, C=O, -CONH-), 1509, 1424 (s, Ar),
1273, 1239, 1070 (s, Ar-O-CH3, Ar-OH), 966, 818 (m, Ph-
1,2H), 708 (C-Cl).
5a
H
= -H), 7.576-7.617 (m, 4H, Ar-H), 7.437-
7.457 (m, 3H, Ar2-H), 7.293-7.322 (d, 2H, J = 8.7 Hz,
H
Ar1-H), 5.503-5.544 (d, 1H, J = 15 Hz,
= -H), 300 MHz.
5b
5c
10.576 (b, 1H, NH), 7.719-7.769 (d, 1H, J = 15 Hz, =
-H), 7.287-7.549 (m, 8H, Ar-H), 6.837-6.888 (d, 1H, J =
15 Hz, = -H).
10.721 (b, 1H, NH), 7.676-7.847 (d, 1H, J = 15 Hz, =
-H), 7.568-7.612 (d, 2H, J = 9 Hz, Ar1-H), 7.201-7.323
(m, 3H, Ar-H), 7.069 (s, 1H, Ar2-H), 6.889-6.930 (d,
1H, J = 9 Hz, Ar2-H), 6.727-6.802 (d, 1H, J = 15 Hz, =
-H), 3.945 (s, 6H, -OCH3) 200 MHz.
10.706 (b, 1H, NH), 7.739-7.790 (d, 1H, J = 15 Hz, =
-H), 7.569-7.598 (d, 2H, J = 8.7 Hz, Ar1-H), 7.285-
7.314 (d, 2H, J = 8.7 Hz, Ar1-H), 7.085-7.097 (d, 2H,
Ar2-H), 6.847-6.874 (d, 1H, J = 8.1 Hz, Ar2-H), 6.705-
6.755 (d, 1H, J = 15 Hz, = -H), 6.050 (s, 2H, -OCH2O-
H) 300 MHz.
10.733 (b, 1H, NH), 7.788-7.862 (d, 1H, J = 15 Hz, =
-H), 7.546-7.712 (q, 4H, Ar-H) 7.280-7.325 (d, 2H, J =
9 Hz, Ar1-H), 6.929-6.972 (d, 2H, J = 8.6 Hz, Ar2-H),
6.753-6.828 (d, 1H, J = 15Hz, = -H), 3.872 (s, 3H,
-OCH3) 300 MHz.
10.681 (b, 1H, NH), 7.561-7.611 (d, 1H, J = 15 Hz, =
-H), 7.551-7.572 (m, 3H, Ar-H), 7.281-7.310 (m, 2H,
Ar-H), 6.783-6.831 (d, 1H, J = 15 Hz, = -H), 6.783-
6.794 (m, 1H, Ar2-H), 6.536-6.554 (m, 1H, Ar2-H).
10.823 (b, 1H, NH), 7.785-7.836 (d, 1H, J = 15.3 Hz, =
-H), 7.502-7.605 (q, 4H, Ar-H), 7.281-7.310 (d, 2H, J =
8.7 Hz, Ar1-H), 6.767-6.794 (d, 2H, J = 8.1 Hz, Ar2-H),
6.685-6.736 (d, 1H, J = 15.3 Hz, = -H), 3.078 (s, 6H,
-NCH3) 300 MHz.
10.831 (b, 1H, NH), 7.719-7.771 (d, 1H, J = 15.6 Hz, =
-H), 7.711-7.740 (d, 2H, J = 8.7 Hz, Ar-H), 7.371-7.400
(d, 2H, J = 8.7 Hz, Ar1-H), 7.337-7.371 (d, 2H, J = 9
Hz, Ar2-H), 7.228-7.263 (d, 2H, J = 9 Hz, Ar2-H),
6.939-6.977 (d, 1H, J = 15.3 Hz, = -H), 3.011 (b, -OH),
300 MHz (CD3COCD3).
5d
5e
5f
5g
5h
5i
agreement with the reaction mechanism reported by Maier.27
Although the reaction mechanism was described, title com-
pounds were reported as 1,2,3-triazole ring derivatives26,28 or
as steadier structures.29 We know that the steadiness of the
structure has something to do with the medium.
10.851 (b, 1H, NH), 8.133-8.183 (d, 1H, J = 15 Hz, =
-H), 7.721-7.750 (d, 2H, J = 8.7 Hz, Ar-H), 7.405-7.455
(d, 1H, J = 15 Hz, = -H), 7.373-7.402 (d, 2H, J = 8.7
Hz, Ar1-H), 7.276-7.351 (m, 2H, Ar2-H), 7.001-7.028
(d, 1H, J = 9 Hz, Ar2-H), 6.885-6.935 (t, 1H, Ar2-H),
2.975 (b, -OH) 300 MHz CD3COCD3.
In order to confirm the reaction mechanism, compound
6 was prepared independently by the follow route of synthe-
sis in Scheme III.
5j
10.925 (b, 1H, NH), 7.755-7.805 (d, 1H, J = 15 Hz, =
-H), 7.707-7.736 (d, 2H, J = 8.7 Hz, Ar-H), 7.457 (s,
1H, Ar2-H), 7.370-7.399 (d, 2H, J = 8.7 Hz, Ar1-H),
7.290-7.318 (d, 2H, J = 8.4 Hz, Ar2-H), 7.161-7.210 (d,
1H, J = 15 Hz, = -H), 6.890-6.918 (d, 1H, J = 8.4 Hz,
Ar2-H), 3.896 (s, 3H, Ar-O-CH3), 2.966 (b, -OH) 300
MHz CD3COCD3.
It is identified as a diazo compound showing strong IR
absorption at 2125 cm-1 of 4 and 2114~2126 cm-1 of 5a~j, as a
dicarbonyl compound showing strong IR absorption at 1670,
1638 cm-1 of 4 and 1603~1676 cm-1 of 5a~j, as a diazo com-

1014 J. Chin. Chem. Soc., Vol. 52, No. 5, 2005
Table 4. MS spectral data for compounds 5a-j
Dong et al.
+
&
No
M
m/z (%)
5a 325 (18)
327 (M+2, 6%), 269 (2), 240 (5.6), 216 (4),
206 (10), 193 (5), 178 (3), 171 (17), 160 (6),
154 (3), 144 (15), 138 (6), 131 (66), 127
(28), 120 (38), 115 (100), 111 (15), 103 (37),
91 (20), 77 (40), 75 (25), 63 (22), 51 (25).
361 (M+2, 10.2%), 278 (0.4), 276 (0.8), 274
(1.9), 233 (3), 207 (3), 205 (9), 195 (2.5),
193 (7), 182 (2), 180 (7), 178 (16), 167 (20),
165 (52), 151 (21), 149 (52), 131 (21), 127
(47), 125 (24), 115 (54), 111 (50), 91 (16),
77 (18), 69 (70), 57 (93), 43 (100).
5b 359 (15)
5c 385 (15)
5d 369 (29)
5e 355 (11)
383 (M+2, 3.5%), 357 (3), 326 (3), 322 (2),
300 (3), 278 (2), 263 (3), 230 (100), 215
(10), 204 (47), 203 (32), 191 (54), 187 (28),
175 (40), 161 (33), 138 (7), 131 (36), 126
(23), 118 (23), 111 (21), 89 (38), 77 (37), 63
(40), 51 (27), 43 (31).
371 (M+2, 12%), 286 (1.2), 284 (5), 248 (2),
215 (56), 214 (73), 204 (3), 188 (89), 186
(52), 185 (23), 175 (43), 164 (9), 159 (69),
145 (44), 135 (41), 127 (64), 117 (31), 111
(40), 102 (78), 91 (38), 89 (87), 77 (48), 75
(90), 63 (93), 51 (50), 43 (100).
357 (M+2, 3%), 270 (1), 201 (15), 184 (2),
174 (19), 161 (35), 156 (15), 145 (42), 139
(18), 131 (22), 127 (19), 118 (11), 115 (11),
111 (23), 107 (19), 102 (32), 99 (16), 91
(26), 89 (21), 77 (37), 63 (30), 51 (24), 44
(100), 43 (48).
317 (M+2, 17%), 260 (6), 258 (17), 252 (13),
237 (4), 230 (10), 202 (3), 193 (5), 178 (4),
167 (8), 161 (12), 154 (5), 150 (7), 138 (12),
134 (24), 126 (26), 121 (100), 111 (28), 105
(56), 99 (27), 94 (26), 78 (82), 65 (71), 51
(55), 43 (25), 39 (50).
370 (M+2, 4%), 342 (5), 340 (4), 312 (1),
283 (3), 237 (2), 214 (10), 213 (14), 204 (1),
188 (8), 186 (35), 185 (52), 174 (36), 158
(100), 144 (22), 131 (15), 127 (21), 121 (5),
115 (41), 111 (19), 102 (12), 99 (16), 91
(14), 77 (17), 75 (19), 63 (19), 57 (37), 43
(42).
342, 316, 307, 279, 237, 233, 214, 165, 157,
154, 147, 138, 136, 121, 120, 118, 115, 111,
107, 105, 91, 89, 84, 79, 77, 59.
Fig. 1. ORTEP drawing of the title compound 5b
showing the atom numbering scheme.
Scheme II
O
O
O
CH
-
H+
CH
3
3
N
+N
+
-
N
3
N
C
N
N
N
O
O
H
N
-N
Cl
O
HN
EtONa/EtOH
1
Cl
3
Cl
4
Cl
5f
315 (50)
Scheme III
O
O
O
CH
-
H+
CH
3
3
N
+N
N
+
-
N
3
N
C
N
5g 368 (15)
N
O
O
H
N
-N
O
HN
EtONa/EtOH
1
Cl
3
Cl
Cl
O
4
Cl
A
B
5h
5i
341
(FAB)
(CH3O)2SO2
reflue
1) EtONa, EtOH;
refiue 4hours
CH
2) (CH3O)2SO2
reflue
3
N
341
342, 307, 289, 284, 282, 256, 233, 214, 196,
179, 175, 171, 166, 152, 145, 144, 137, 127,
116, 115, 111.
N
OCH
3
(FAB)
N
5j
371
(FAB)
372, 307, 289, 279, 273, 232, 214, 165, 157,
155, 154, 147, 136, 135, 134, 121, 120, 118,
115, 111, 107, 105, 91, 89, 87, 84, 79, 77,
59, 56279.
Cl
6

Substituted-2-diazo-3-oxopent-4-enoic Acid Amides
J. Chin. Chem. Soc., Vol. 52, No. 5, 2005 1015
1
2003, 11(17), 3633.
pound showing -CONH- H NMR peak at 10.216 ppm of 4
H
11. Himanshu; Tyagi, R.; Olsen, C. E.; Errington, W.; Parmar, V.
S.; Prasad, A. K. Bioorganic & Medicinal Chemistry 2002,
10(4), 963.
and 10.576~10.925 ppm of 5a~j and showing
1H
H
NMR dual peak 7.919~8.183 ppm, 5.053~7.445 ppm, J =
15~15.3 Hz of 5a~j there is not 1,2,3-triazole ring system in
molecule structure of compounds.27 The bond lengths of
N2-N3 1.116(6) Å in compound 5 aren’t in agreement with
the values reported for 1,2,3-triazole ring. The bond length is
shorter than N=N (N1-N2 1.361(5) Å, N2-N3 1.295(5) Å).
The ring system and all atoms are planar in intermo-
lecular, there is the conjugate of the pi-pi. It is shown in Fig. 1
and Fig. 2.
12. Velazquez, S.; Alvarez, R.; Perez, C.; Gago, F.; De, C.;
Balzarini, J.; Camarasa, M. J. Antivir. Chem. Chemoter.
1988, 9, 481.
13. Garanti, L.; Molteni, G. Tetrahedron Lett. 2003, 44(6), 1133.
14. Romines, K. R.; Watenpaugh, K. D.; Howe, W. J.; Tomich, P.
K.; Lovasz, K. D.; Morris, J. K.; Janakiraman, M. N.; Lynn,
J. C.; Horng, M.-M.; Chong, K.-T.; Hinshaw, R. R.; Dolak, L.
A. J. Med. Chem. 1995, 38, 4463.
15. Romines, K. R.; Morris, J. K.; Howe, W. J.; Tomich, P. K.;
Horng, M.-M.; Chong, K.-T.; Hinshaw, R. R.; Anderson, D.
J.; Strohbach, J. W.; Turner, S. R.; Mizsak, S. A. J. Med.
Chem. 1996, 39, 4125.
There are the strong interactions of hydrogen bond on
the molecular stacking [N1-H1A 0.90 H1A······O2 1.95 N1-
H1A······O2 2.697(5) Å N1-H1A······O2 139.7(°)] but weak
intermolecular interaction of the pi-pi.
16. Skulnick, H. I.; Johnson, P. D.; Aristoff, P. A.; Morris, J. K.;
Lovasz, K. D.; Howe, W. J.; Watenpaugh, K. D.; Janakiraman,
M. N.; Anderson, D. J.; Reischer, R. J.; Schwartz, T. M.;
Banitt, L. S.; Tomich, P. K.; Lynn, J. C.; Horng, M.-M.;
Chong, K.-T.; Hinshaw, R. R.; Dolak, L. A.; Seest, E. P.;
Schwende, F. J.; Rush, B. D.; Howard, G. M.; Toth, L. N.;
Wilkinson, K. R.; Kakuk, T. J.; Johnson, C. W.; Cole, S. L.;
Zaya, R. M.; Zipp, G. L.; Possert, P. L.; Dalga, R. J.; Zhong,
W.-Z.; Williams, M. G.; Romines, K. R. J. Med. Chem. 1997,
40, 1149.
ACKNOWLEDGEMENTS
The authors with to acknowledge this project is sup-
ported by NNSFC (chuangxin qunti) and Lanzhou University
SKLAOC.
17. Gupta, S. P.; Babu, M. S.; Kaw, N. J. Enzyme Inhib. 1999,
14, 109.
Received January 3, 2005.
18. Tait, B. D.; Hagen, S.; Domagala, J. M.; Ellsworth, E. L.;
Gajda, C.; Hamilton, H. W.; Vara Prasad, J. V. N.; Ferguson,
D.; Graham, N.; Hupe, D.; Nouhan, C.; Tummino, P. J.;
Humblet, C.; Lunney, E. A.; Pavlovsky, A.; Rubin, J.;
Gracheck, S. J.; Baldwin, E. T.; Bhat, T. N.; Erickson, J. W.;
Gulnik, S. V.; Liu, B. J. Med. Chem. 1997, 40, 3781.
19. Vara Prasad, J. V. N.; Para, K. S.; Tummino, P. J.; Ferguson,
D.; Mcquade, E. J.; Lunney, E. A.; Rapundalo, S. T.; Batley,
B. L.; Hingorani, G.; Domagala, J. M.; Gracheck, S. J.; Bhat,
T. N.; Liu, B.; Baldwin, E. T.; Erickson, J. W.; Sawyer, T. K.
J. Med. Chem. 1995, 38, 898.
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