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HETEROCYCLES, Vol. 68, No. 3, 2006
(CDCl3) δ 2.82(t, J = 7.2 Hz, 2H), 3.17(t, J = 7.2 Hz, 2H), 3.65(s, 2H), 4,01(s, 2H), 4.15(bs, 1H), 7.27(d, J
= 7.2 Hz, 1H), 7.33(d, J = 7.2 Hz, 1H), 7.40(dd, J = 8.4, 4.6 Hz, 1H), 8.10(dd, J = 8.4, 1.6 Hz, 1H), 8.85(dd,
J = 4.6, 1.6 Hz, 1H). 13C NMR (CDCl3) δ 45.5, 52.1, 54.5, 70.6, 117.5, 119.1, 121.4, 127.9, 128.2, 134.9,
138.4, 148.7, 152.2. Anal. Calcd for C13H15N3O: C, 68.10; H, 6.59; N, 18.32. Found: C, 68.06; H, 6.67; N,
18.33. LR EI-MS: m/z 229 (M+).
Synthesis of 3,3´-ethane-1,2-diylbis-3,4-dihydro-2H-[1,3]oxazino[5,6-h]quinoline (4): Under vigorous
stirring a mixture of ethylenediamine (0.34 mL, 5 mmol) and 8-hydroxyquinoline (1.5 g 10 mmol) was
dissolved in dioxane (10 mL) and formaldehyde (1.5 mL, 20 mmol) was slowly added. Stirring was
continued for 4 h at rt until a precipitate appeared. The solid was filtered off and washed with water (1.83
o
g, 92%). Recrystallization from ethanol gave a white solid: mp 175-176 C. IR (KBr) 3030, 2930, 2860,
1
1480, 1435, 1250; H NMR(CDCl3) δ 313(s, 4H), 4.22(s, 4H), 5.21(s, 4H), 7.14(d, J = 8.4 Hz, 2H),
13
7.33(d, J = 8.4 Hz, 2H), 7.39(dd, J = 8.3, 4.2 Hz, 2H), 8.09(dd, 2H), 8.90(dd, J = 8.3, 1.7 Hz, 2H). C
NMR (CDCl3) δ 50.2, 50.1, 50.7, 83.6, 119.1, 121.2, 126.1, 128.2, 135.9, 136.1, 139.4, 149.5, 149.6.
Anal. Calcd for C24H22N4O2: C, 72.34; H, 5.56; N, 14.06. Found: C, 72.38; H, 5.27; N, 14.07.
ACKNOWLEDGEMENTS
The authors acknowledge financial support for this research from Dirección Nacional de Investigaciones
(DINAIN) of Universidad Nacional de Colombia. We are also grateful to Departamento de Química,
Universidad Nacional de Colombia. M.A.N. thanks Colciencias for a fellowship from “Apoyo a la
comunidad Científica Nacional, a través de los programas de Doctorado Nacionales –Año 2005”.
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