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
[...] Read more.
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
3N 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
2O afford the corresponding 1,3,4-thiadiazol-2-yl acetamide derivative
16. The structures of the synthesized compounds were confirmed by IR,
1H-NMR/
13C-NMR and mass spectral studies. Compound
14 showed promising effects against the tested Gram positive and negative bacteria and fungi.
Full article