Abstract:
In view of the extensive naMa! occurrence and biological importance of
dih\drohenzofuron and luran derivatives it was planned to develop a general and facile
method for the synthesis of dihydrofurans through metal mediated eatalYL:ed reactions of
qclic diazocarbonyl compounds. An efficient method lor the synthesis of 4-oxo-2,
3.4.5,6. 7-hexahydro-benzofurJn- 2-yl-acetale deri valive, 10-12, 2-chloromethyl- 3,5,6,7-
tctrahydro-2H-benzofuran-4-ones 28,29,30 through the rhodium pivalale catalyzed
reaction of 2-diazo-cyclohexane-l,3-diones 6-S with vinyl acetate and allyl chloride,
respectively in mild condition is reported.
Synthesis of 2-phenyl-6, 7_dihydro_51l_benzol\.u'an-4_ones 14,16,18,and 2-ethoxy methyl
3j.6,7-tetrahydro-2H-benzofuran-4-ones 21,23,25 are also developed by rhodium
catalyst reaction of 2_diazo-cyelohexane_I,3_diones with phenyl acetylene and allyl ethyl
ether respectively under the same reaction condition. In case of phenyl acetylene and allyl
ethyl ether spiro compound l_phenyl_spiro(2,5]oct_l_ene_4,8_diones 15,17,18 and 1-
elhoxymethyl spiro[2,5]octane-4,8-diones 22,24,26 were obtained respectively as by
products.
o
R,-~+-Jld"-Ac
R'IO_12
o
RI-0-rCI R, 28.30
o
RI~
"- 14. t6,18
o
.AAo',/ RI~O -...r
R2 22,24,26
Where,
All ,the synthesized products were characterized by ~-pectraJ data obtained from IR, UV
and lHNMR. All synthesized compounds were tested antibacterial and antifungal activity,
some of them demonstrated mild to moderate antimicrobial activity against most of the
test organism.
