1208 J. Chin. Chem. Soc., Vol. 50, No. 6, 2003
Moustafa et al.
[C24H19N3O2; 381].
[C22H19N5O; 369].
4b: 65% yield; as red crystals mp: 280-281 °C
[C24H18N4O4; 426].
Received December 3, 2002.
REFERENCES
4c: 69% yield, as pale brown crystals mp: 272-274 °C
[C25H21N3O3; 411].
Reactions of chalcones (4a-c) with malononitrile
A mixture of chalcone 4 (0.1 mol), malononitrile (0.66
g, 0.1 mol) and ammonium acetate (6.16 g, 0.8 mol) was
refluxed in ethanol (30 mL) for 6 h on a water-bath; the
cooled contents were then poured into crushed ice with con-
stant stirring, and the resulting solid was washed with water
and the residue was crystallized from ethanol to give 5a-c.
5a: 72% yield, as yellowish crystals mp: 222-224 °C
[C27H20N6O; 444].
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5b: 72% yield, as pale orange crystals mp: 259-260 °C
[C27H19N7O3; 489].
5c: 72% yield, as yellow crystals mp: 227-238 °C
[C28H22N6O2; 474].
Reactions of chalcones (4a-c) with hydroxylamine hydro-
chloride
Anhydrous sodium acetate (0.73 g, 0.01 mol) dissolved
in a minimum amount of hot acetic acid was added to the so-
lution of hydroxylamine hydrochloride (0.7 g, 0.01 mol) in
ethanol (20 mL). This solution was added to a solution of
chalcones 4a-c (0.01 mol) in ethanol (20 mL). The mixture
was refluxed for 6 h, concentrated and neutralized with
NaOH. The product thus isolated was filtered and crystal-
lized from ethanol to yield 6a-c.
6a: 78% yield, as pale yellow crystals mp: 219-220 °C
[C24H18N4O2; 394].
6b: 70% yield, as yellowish crystals mp: 230-232 °C
[C24H17N5O4; 439].
6c: 69% yield, as yellow crystals mp: 227-228 °C
[C25H20N4O3; 424].
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white crystals mp: 120-122 °C [C22H17N3O2; 355].
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3-(4-Benzoylhydrazoneanilinomethyl)quinoxalin-2(1H)-
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A solution of ketone compound 8 (3.55 g, 0.01 mol) and
hydrazine hydrate (0.01 mol) in ethanol (30 mL) was heated
under reflux for one h; the reaction mixture was cooled, the
solid separated was filtered and crystallized from ethanol to
give 65% yield of 9, as yellowish crystals mp: 154-155 °C