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HETEROCYCLES, Vol. 75, No. 9, 2008
16.08. Found: C, 64.39; H, 7.65; N, 15.89. IR (cm-1): 2964 (NH), 1662 (CO); 1H NMR (CDCl3): δ, ppm =
2.49 (m, 7H, morpholin-H, Me), 3.72 (m, 6H, morpholin-H, CH2), 7.02-7.38 (m, 5H, Ar-H), 11.88 (br,
13
1H, NH, D2O exchangeable); C NMR (CDCl3): δ, ppm = 197.5 (CO), 143.8, 138.1, 130.1 (2C), 122.9,
114.4 (2C), 67.7 (2C), 53.4, 53.2 (2C), 24.9. MS: m/z (%) 261 (M+, 15), 169 (55), 105 (50), 100 (60), 77
(100).
1-Morpholino-2-(2-phenylhydrazono)pentan-3-one (2d)
o
Yellow crystals; yield 87 %; mp 108-110 C. Anal. Calcd for C15H21N3O2 (275.3): C, 65.43; H, 7.69; N,
1
15.26. Found: C, 65.62; H, 7.90; N, 15.43. IR (cm-1): 2938 (NH), 1661 (CO); H NMR (DMSO-d6): δ,
ppm = 1.16 (t, 3H, J = 8, Me) 2.48 (m, 4H, morpholin-H), 2.99 (q, 2H, J = 8, CH2), 3.72 (m, 6H,
13
morpholin-H, and CH2), 7.01-7.38 (m, 5H, Ar-H), 11.82 (br, 1H, NH, D2O exchangeable); C NMR
(DMSO-d6): δ, ppm = 200.4 (CO), 143.9, 137.4, 130.1 (2C), 122.8, 114.4 (2C), 67.7 (2C), 53.4, 53.5 (2C),
29.9, 9.6. MS: m/z (%) 275 (M+, 25), 183 (85), 105 (85), 100 (90), 77 (100).
4-Morpholino-4-phenyl-3-(2-phenylhydrazono)butan-2-one (2e)
Yellow crystals; yield 80 %; mp 149-150 oC. Anal. Calcd for C20H23N3O2 (337.42): C, 71.19; H, 6.87; N,
12.45. Found: C, 70.93; H, 7.20; N, 12.66. IR (cm-1): 2974 (NH), 1662 (CO); 1H NMR (CDCl3): δ, ppm =
2.36 (m, 7H, morpholin-H and Me), 3.74 (m, 4H, morpholin-H), 4.93 (s, 1H, CH), 6.99-7.45 (m, 10H,
13
Ar-H), 12.68 (br, 1H, NH, D2O exchangeable); C NMR (CDCl3): δ, ppm = 195.4 (CO), 14.86, 13.78,
136.5, 129.5 (2C), 128.7 (2C), 128.2, 127.7 (2C), 122.2, 113.8 (2C), 67.5, 66.2 (2C), 51.7 (2C), 24.3. MS:
m/z (%) 337 (M+, 85), 250 (100), 207 (20), 176 (20), 105 (20), 77 (10).
1-Morpholino-1-phenyl-2-(2-phenylhydrazono)pentan-3-one (2f)
Yellow crystals; yield 83 %; mp 133-135 oC. Anal. Calcd for C21H25N3O2 (351.45): C, 71.77; H, 7.17; N,
1
11.96. Found: C, 71.64; H, 7.38; N, 11.96. IR (cm-1): 2976 (NH), 1668 (CO); H NMR (DMSO-d6): δ,
ppm = 0.94 (t, 3H, J = 8, Me) 2.50-3.54 (m, 10H, morpholin-H and CH2), 4.93 (s, 1H, CH), 6.99-7.45 (m,
10H, Ar-H), 12.68 (br, 1H, NH, D2O exchangeable); 13C NMR (DMSO-d6): δ, ppm = 198.2 (CO), 142.9,
138.1, 136.6, 129.5 (2C), 129.2 (2C), 128.3, 127.7 (2C), 122.1, 113.7 (2C), 67.7, 66.2 (2C), 51.7 (2C),
28,9, 8.7. MS: m/z (%) 351 (M+, 25), 264 (100), 259 (35), 207 (25), 176 (15), 105 (20), 77 (30).
Synthesis of 4-(1H-benzo[1,2,3]triazol-1-yl)-3-(2-phenylhydrazono)butan-2-one (4)
A mixture of 1a (1.62 g, 0.01 mol), formaldehyde (0.30 g, 0.01 mol) and benzotriazole (1.19 g, 0.01 mol)
in dioxane (10 mL) were refluxed for 1-2 h (monitored by TLC). The reaction mixture was evaporated
under reduced pressure in vacuum yielding a crude product. This crude product contains compounds 4
and 6a. These were separated by long column chromatography using a mixture of petroleum ether ( bp
60-80) and EtOAc (3:1) as an eluent. Compound 4 when separated from column chromatography was
recrystallized from petroleum ether (bp 60-80) and gave yellow crystals; yield 55 %; mp 127-129 oC.
Anal. Calcd for C16H15N5O (293.33): C, 65.52; H, 5.15; N, 23.88. Found: C65.55; H, 5.44; N, 23.59. IR