Molecules 2007, 12
2072
2222 (CN), 1618 (C=O) and 1539 (C=N); MS: (M+) 342; Anal. Calcd. for C19H14N6O (342.36): C,
66.66; H, 4.12; N, 24.55; Found: C, 66.56; H, 4.20; N, 24.59.
2-{N′-[2-Furan-2-yl-2-oxo-1-(pyridin-2-yliminomethyl)ethylidene]hydrazino}benzonitrile (9g). Brown
crystals (from ethanol); m.p. 259 ºC; IR νmax cm-1: 3500 (br, NH), 3105 (CH aromatic), 2220 (CN),
1631 (C=O) and 1549 (C=N); MS: (M+) 343; Anal. Calcd. for C19H13N5O2 (343.35): C, 66.47; H,
3.82; N, 20.40; Found: C, 66.50; H, 3.89; N, 20.35.
Methyl
2-(N′-{1-[(1H-Benzoimidazol-2-ylimino)-methyl]-2-furan-2-yl-2-oxo-ethylidene}hydrazino)
1
benzoate (9h). Brown crystals (from 2:1 ethanol/dioxane); m.p. 240ºC; H-NMR: δ = 4.0 (s, 3H,
OCH3), 6.83 (dd, 1H, furyl H-4), 7.22-7.25 (m, 4H, imidazole-H), 7.36 (m, 1H, furyl H-3), 7.63-7.99
(m, 4H, Ar-H), 8.08 (d, 1H, furyl H-5), 9.47 (s, 1H, CH olefinic), 12.11 (s, 1H, NH imidazole) and
15.85 (s, 1H, NH hydrazone) ppm; MS: (M+) 415; Anal. Calcd. for C22H17N5O4 (415.41): C, 63.61; H,
4.12; N, 16.86; Found: C, 63.67; H, 4.22; N, 16.90.
Methyl 2-(N′-{1-[(1H-Benzoimidazol-2-ylimino)-methyl]-2-oxo-2-(1H-pyrrol-2-yl)-ethylidene]hydra-
zino)benzoate (9i). Dark yellow crystals (from 2:1 ethanol/dioxane); m.p. 281ºC; IR νmax cm-1 (shows
complex spectra due to H-bond between O and NH): 3480 (NH pyrrolyl), 3383 (NH imidazole),
3081(CH aromatic),1718 (C=O ester), 1656 (C=O ketone) and 1571 (C=N); 1H-NMR: δ = 3.96 (s, 3H,
OCH3), 6.54 (m, 1H, pyrrolyl H-4), 6.95-7.02 (m, 2H, pyrrolyl H-3, H-5), 7.21-7.32 (m, 4H, imidazole
H), 7.54-7.97 (m, 4H, Ar-H), 9.22 (s, 1H, CH olefinic), 11.43 (s, 1H, NH pyrrolyl), 11.65 (s, 1H, NH
imidazole) and 14.25 (s, 1H, NH hydrazone) ppm; MS: (M+) 414; Anal. Calcd. for C22H18N6O3
(414.43): C, 63.76; H, 4.38; N, 20.28; Found: C, 63.79; H, 4.40; N, 20.30.
Methyl
2-(N′-{1-[(1H-Benzoimidazol-2-ylimino)-methyl]-2-(4-chlorophenyl)-2-oxo-2-ethylidene]-
hydrazino} benzoate (9j). Orange crystals (from 2:1 ethanol/dioxane); m.p. 257 ºC; IR νmax cm-1:
(shows complex spectra due to H-bond between O and NH) 3354 (NH imidazole), 1690 (C=O ester),
1640 (C=O ketone) and 1586 (C=N); MS: (M+-18) 441; Anal. Calcd. for C24H18N5O3Cl (459.90): C,
62.68; H, 3.95; N, 15.23; Found: C, 62.58; H, 3.90; N, 15.33.
Methyl
2-{N′-[1-(Benzothiazol-2-yliminomethyl)-2-oxo-2-(1H-pyrrol-2-yl)-ethylidene]-hydrazino}-
benzoate (9k). Brown crystals (from methanol); m.p. 189 ºC; IR νmax cm-1: 3492, 3224 (2NH), 3023
1
(CH aromatic), 1720 (C=O ester), 1664 (C=O ketone) and 1575 (C=N); H-NMR: δ = 3.96 (s, 3H,
OCH3), 6.41 (m, 1H, pyrrolyl H-4), 6.75 (d, 2H, pyrrolyl H-3), 6.89 (s, 1H, CH olefinic), 6.95 (d, 1H,
pyrrolyl H-5), 7.22, 7.36 (d, 2H, benzothiazole H-4, H-7), 7.38-7.44 (m, 2H, benzothiazole H-5, H-6),
7.53 (s, 1H, NH pyrrolyl), 7.62-7.69 (m, 2H, Ar H-4, H-5), 7.89, 7.91 (d, 2H, Ar H-3, H-6), and 14.46
13
(s, 1H, NH hydrazone) ppm; C-NMR: δ = 52.46 (OCH3), 110.33, 121.24, 126.57, 131.30 (pyrrolyl
carbon), 113.21, 114.03, 116.90, 119.54, 134.21, 136.84 (C6H4-CO2Me-o), 121.58, 123.18, 124.77,
134.32, 137.45 (C6H4NS), 140.50 (C=N-N), 144.82 (N-C-S), 165.27 (HC=N), 167.31 (COOCH3) and
173.42 (C=O) ppm; MS: (M+) 431; Anal. Calcd. for C22H17N5O3S (431.48): C, 61.24; H, 3.97; N,
16.23; Found: C, 61.34; H, 3.87; N, 16.40.