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Med Chem Res (2011) 20:274–279
Experimental
119.2–149.3 (Ar–C), 164.8, 168.2, 176.0 (C=N of s-tri-
azine), 163.27 (CO).
7c: IR (mmax in cm-1): 1671 ([C=O of amide, C=O str),
3342 (NH) and 1326 (CN), 1519, 1377 (NO2), 3084
(Aromatic CH str). 1H-NMR d ppm: 10.11 (s, 1H, CONH–,
D2O exchangeable), 4.21 (s, 1H, NH), 9.25 (s, 1H, NH–
Ar), 7.07–8.29 (m, 12H, Ar–H). 13C-NMR d ppm:
119.5–147.7 (Ar–C), 165.1, 168.7, 177.2 (C=N of s-tri-
azine), 163.11 (CO).
7d: IR (mmax in cm-1): 1670 ([C=O of amide, C=O str),
3340 (NH) and 1320 (CN), 1519, 1377 (NO2), 3077
1
(Aromatic CH str), 1517, 1371 (NO2, N=O str.). H-NMR
All the melting points were taken in open capillaries tube
and are uncorrected. The purity of compounds was checked
routinely by TLC (0.5-mm thickness) using silica gel,
G-coated aluminium, plates (Merck), and spots were
visualized by exposing the dry plates in iodine vapours. IR
spectra (mmax in cm-1) were recorded on Shimadzu FTIR
spectrophotometer using KBr or Nujol technique.1H- and
13C-NMR spectra were observed on a Bruker’s WM 400
FT MHz NMR instrument using CDCl3 or DMSO-d6 as
solvent and TMS as internal reference (chemical shifts in d
ppm). The elemental analyses (C, H, N) of compounds
were performed on Carlo Erba 1108 elemental analyzer.
d ppm: 10.15 (s, 1H, CONH, D2O exchangeable), 4.14 (s,
1H, NH), 9.25 (s, 1H, NH–Ar), 7.07–8.29 (m, 12H, Ar–H).
13C-NMR d ppm: 111.7–147.7 (Ar–C), 164.7, 168.7, 176.9
(C=N of s-triazine), 164.77 (CO).
N0-(4-(substituted phenylamino)-6-(pyridin-2-ylamino)-
1,3,5-triazin-2-yl) isonicotino-hydrazide 7a–r
7e: IR (mmax in cm-1): 1675 ([C=O of amide, C=O str),
3310 (NH) and 1325 (CN), 3090 (Aromatic CH str), 835
1
The designated compounds were prepared in one pot by a
three-step reaction as follows: The first step consists of
nucleophilic substitution(Thruston et al., 1951) of one
chlorine atom of cyanuric chloride, 1 in presence of ace-
tone with 2-aminopyridine, 2 to synthesize compound 3
(0–5°C, 0.5–1.0 h). The second step involves further sub-
stitution(Thruston et al., 1951) of the second chlorine atom
in the presence of acetone with isonicotinic acid hydrazide,
4 to give compound 5 (30–35°C, 3.0–3.5 h). At the third
step, the third chlorine atom was substituted (Modha et al.,
2001) with various aromatic amines, 6a–r (reflux, 5–6 h) in
the presence of aqueous dioxane (Modha et al., 2001) to
obtain a series of compounds, 7a–r (Scheme 1). The pro-
gress of reaction was monitored by TLC using ace-
tone:toluene (8:2) as eluent. After completion of reaction,
the stirring was stopped, and the solution was treated with
crushed ice. The product obtained was filtered and dried.
The crude products were purified by crystallization from
acetone to give the titled compounds. The physical and
analytical data of novel compounds are given in Table 1.
Their characteristic spectral data are as follows:
(C–Cl str). H-NMR d ppm: 10.14 (s, 1H, CONH, D2O
exchangeable), 4.09 (s, 1H, NH), 9.27 (s, 1H, NH–Ar),
7.71–8.91 (m, 12H, Ar–H). 13C-NMR d ppm: 111.9–147.9
(Ar–C), 163.2, 169.9, 176.7 (C=N of s-triazine), 164.5
(CO).
7f: IR (mmax in cm-1): 1676 ([C=O of amide, C=O str),
3315 (NH) and 1320 (CN), 3095 (Aromatic CH str), 830
1
(C–Cl str). H-NMR d ppm: 10.15 (s, 1H, CONH, D2O
exchangeable), 4.04 (s, 1H, NH), 9.25 (s, 1H, NH–Ar),
7.70–8.90 (m, 12H, Ar–H). 13C-NMR d ppm: 111.9–147.7
(Ar–C), 163.0, 169.7, 176.9 (C=N of s-triazine), 164.0
(CO).
7g: IR (mmax in cm-1): 1677 ([C=O of amide, C=O str),
3319 (NH) and 1327 (CN), 3099 (Aromatic CH str), 837
1
(C–Cl str). H-NMR d ppm: 10.19 (s, 1H, CONH, D2O
exchangeable), 4.27 (s, 1H, NH), 9.29 (s, 1H, NH–Ar),
7.74–8.92 (m, 12H, Ar–H). 13C-NMR d ppm: 111.7–147.9
(Ar–C), 163.7, 169.9, 176.7 (C=N of s-triazine), 164.9
(CO).
7h: IR (mmax in cm-1): 1672 ([C=O of amide, C=O str),
3315 (NH) and 1327 (CN), 3099 (Aromatic CH str), 832
1
(C–Cl str). H-NMR d ppm: 10.15 (s, 1H, CONH, D2O
Spectral data of synthesized compounds, 7a–r
exchangeable), 4.27 (s, 1H, NH), 9.29 (s, 1H, NH–Ar),
7.22–8.59 (m, 12H, Ar–H). 13C-NMR d ppm: 111.7–149.9
(Ar–C), 163.5, 169.7, 176.9 (C=N of s-triazine), 164.9
(CO).
7a: IR (mmax in cm-1): 1670 ([C=O of amide, C=O str),
3340 (NH) and 1325 (CN), 3085 (Aromatic CH str).
1H-NMR d ppm: 10.19 (s, 1H, CONH–, D2O exchange-
able), 4.11 (s, 1H, NH), 9.24 (s, 1H, NH–Ar), 7.11–8.12
(m, 13H, Ar–H). 13C-NMR d ppm: 119.1–147.2 (Ar–C),
164.7, 168.1, 176.9 (C=N of s-triazine), 163.27 (CO).
7b: IR (mmax in cm-1): 1672 ([C=O of amide, C=O str),
3345 (NH) and 1327 (CN), 1517, 1371 (NO2), 3081
(Aromatic CH str). 1H-NMR d ppm: 10.10 (s, 1H, CONH–,
D2O exchangeable), 4.09 (s, 1H, NH), 9.25 (s, 1H, NH–
Ar), 7.21–8.31 (m, 12H, Ar–H). 13C-NMR d ppm:
7i: IR (mmax in cm-1): 1674 ([C=O of amide, C=O str),
3322 (NH) and 1322 (CN), 3091 (Aromatic CH str), 1311
1
(CH3, C–H bend.). H-NMR d ppm: 10.11 (s, 1H, CONH,
D2O exchangeable), 4.18 (s, 1H, NH), 9.11 (s, 1H, NH–
Ar), 7.14–8.14 (m, 12H, Ar–H). 13C-NMR d ppm:
119.1–147.1 (Ar–C), 160.1, 171.1, 179.1 (C=N of s-tri-
azine), 164.1 (CO).
7j: IR (mmax in cm-1): 1675 ([C=O of amide, C=O str),
3320 (NH) and 1320 (CN), 3089 (Aromatic CH str), 1309
123