Molbank 2007, M532 |
Synthesis of 2-(4-benzyl-3-methyl-6-oxopyridazin-1(6H)-yl)acetohydrazide
Nour-Eddine Benchat *, Abderrahmane
Anaflous, Said Abouricha,
Mohammed Ramdani and Abderazak
Benalla
Department of Chemistry, University
Mohamed I, Sciences Faculty, 60000
*Author to whom correspondence should be addressed. E-mail: [email protected]
Received: 3 January 2006 / Accepted: 24 June 2006 / Published: 31 May 2007
Keywords:
pyridazin-3(2H)-one, N-alkylation, anticonvulsive agents.
Pyridazines are of chemical and biological
interest. They have been reported to be anticonvulsive agents [1], [2].
Furthermore, BELLASIO et al. have described the antihypertensive effects of hydrazinopyridazine compounds [3]. In continuation of this
line of investigation, we have synthesized compound (I); it will be subjected to further pharmacological
investigations, especially tests of its anticancer activity.
To (0.86 g,
3 mmol) of ethyl (4-benzyl-3-methyl-6-oxopyridazin-1(6H)-yl)acetate (I), was added 10 ml of hydrazine hydrate. The mixture was placed
in a pyrex tube which was
then introduced into a Maxidigest MX 350 Prolabo microwave [4] monomode
reactor and refluxed for 10 min on 60 w as irradiation power. After cooling,
the product precipitates, and then is recrystallised
in absolute ethanol, yield: 85 % of (II)
solid.
Melting point: 197-
IR (KBr, cm-1): 3350 (NH), 1680, 1620 (C = O)
1HNMR (300.14 MHz, CDCl3) d (ppm): 2.50 (s, 3H, CH3). 2.53 (s, 2H, NH2), 3.79 (s, 2H, CH2), 4.84 (d, 2H, CH2), 6.54 (s, 1H, H4), 7.31 (m, 5H, H aromatic), 7.73 (s, 2H, NH2).
13CNMR (75 MHz, CDCl3) d (ppm): 19.55 (CH3), 38.82 (CH2), 54.73
(CH2), 127.77 (CH aromatic), 128.26 (CH aromatic), 129.48 (2 CH aromatic),
135.77, 146.50, 147.34, 161.09 (C=O), 168.32 (C=O).
References:
1. Wermuth, C.G.; Leclerc, G.; Melounov, P. Chim. Ther. 1971, 2, 109.
2. Laborit, H.; Weber, B.; Wermuth,
C.G.; Delbarre, B.; Chekler,
C.; Baron, C.; Rosen Garten, H. AGRESSOLOGIE 1965, 6, 415.
3. Bellasio, E. ; Parravicini, F. ; Testa,
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