Abstract:
Reaction of 3-(4-substitutedbenzoyl)propionic acid with appropriate aromatic
aldehydes in the presence of triethylamine in acetic anhydride gave 3-arylidene-5-(4-
substititutedphenyl)furan-2(3H)-ones. Reaction of furanones with benzylamine gave
γ-ketobenzylamides which were then cyclized to 1-benzyl-3-arylidene-5-(4-
substituted phenyl)-1H-pyrrol-2-(3H)-ones by refluxing with 6N-HCl. Two series of
furanones and pyrrolones were synthesized. The synthesized compounds were
evaluated for antioxidant, cytotoxicity and urease inhibition activities. These
compounds showed non significant antioxidant activity, nil brine shrimp lethality and
low to moderate urease inhibition activity.
Reaction of hitherto unknown 4-chloro-3-(2,2,2-trifluoroacetyl)-2H-chromen-
2-one with different commercially available anilines gave 3-(trifluoroacetyl)-4-
(arylamino)-2H-chromen-2-ones
which
were
then
successfully
cyclized
to
7-(trifluoromethyl)-6H-chromeno[4,3-b]quinolin-6-ones with conc. H2SO4.
Suzuki cross-coupling reaction of methyl-3-bromothiophene-2-carboxylate
and
ethyl-2-bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
methoxy phenylboronic acids gave the
successfully
cyclized
to
with
o-
arylated products which were then
thieno[2,3-c]chromen-4-ones
and
7,8,9,10-
tetrahydrobenzothieno[3,2-c]chromen-6-ones via BBr3 mediated lactonization.
The Sonogashira cross-coupling reaction of methyl-3-bromothiophene-2-
carboxylate and 2-bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile with
terminal alkynes gave respective alkynyl products. The ester and nitrile groups of
these substituted thiophenes were then converted into amides which were then
cyclized to 5-substituted-thieno[2,3-c]pyridin-7(6H)-ones and 3-substituted-5,6,7,8-
tetrahydrobenzothieno[3,2-c]pyridin-1(2H)-ones via base-promoted-cyclization.
4,5-Disubstituted thieno[3,2-b]pyridin-7(4H)-ones were synthesized by Pd-
catalyzed tandem amination reaction of α,β-ynone with commercailly available
anilines/amines. The method provides an efficient
thienopyridinones.
