Abstract
Preparation of 4-benzyl-2-substituted phthalazin-1-one derivatives
2-8
is reported. Condensation of 4-benzyl-1-chlorophthalazine (
9
) with a series of different nucleophiles gave 4-benzylphthalazin-1-ylamino derivatives (
10-13
and
16
) and 4-amino-2-[
N
′-(4-benzylphthalazin-1-yl)-hydrazino]-6-arylpyrimidine-5-carbonitriles (
14a
,
b
). Interaction of
9
with ambident anions was also studied. 5-Benzyl-6,6a,12-triazobenzo[
a
]-anthracen-7-one (
15
) is obtained from
9
and anthranilic acid derivatives. Treatment of
16
with (EtO)
3
CH/Ac
2
O under reflux afforded the corresponding ethoxymethylene derivative
17
, while aqueous ammonium hydroxide treatment afforded carboxamide derivative
18
. The structures of the newly synthesized derivatives were confirmed by their elemental analysis, IR,
1
H NMR,
13
C NMR and mass spectral studies. Antimicrobial activities of some selected compounds were also studied and some of these were found to exhibit promising effects against Gram-positive and Gram-negative bacteria and fungi.