Abstract
Vilsmeier formylation of 2-(1-phenylhydrazonoethyl)naphtho[2,1-
b
]furan (
2
) gave 3-naphtho[2,1-
b
]furan-2-yl-1-phenyl-1
H
-pyrazole-4-carbaldehyde (
3
), which was reacted with C- and
N
-nucleophiles to afford naphthofuranpyrazol derivatives
4-8
. Treatment of 2-[(3-(naphtho[2,1-
b
]furan-2-yl)-1-phenyl-
1H-
pyrazol-4-yl)methylene]-malononitrile (
4a
) with reactants having active hydrogen and Et
3
N gave the corresponding pyrazoline, pyran and chromene addition product derivatives
10
,
12
and
13
, consisting of three different connected heterocyclic moieties. Reaction of 1-((3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1
H
-pyrazol-4-yl) methylene)-2-phenylhydrazone (
6b
) with AcONa and ethyl bromoacetate or chloroacetone afforded the thiazolidinone and methylthiazole derivatives
14
and
15
, respectively. In addition, intramolecular cyclization of
6d
with Ac
2
O afford the corresponding 1,3,4-thiadiazol-2-yl acetamide derivative
16
. The structures of the synthesized compounds were confirmed by IR,
1
H-NMR/
13
C-NMR and mass spectral studies. Compound
14
showed promising effects against the tested Gram positive and negative bacteria and fungi.