1887-18936-Fluorobenzo[b]pyran-4-one
1 on condensation with aromatic
aldehydes yields 3-arylmethylene-6-fluoro-2,3-dihydrobenzo[b]pyran-4-ones 2 which on treatment with
phenylhydrazine and thiourea gives the pyrazole and pyrimidine thione
derivatives 3 and 4, respectively. Compound 4 reacts with chloroacetic acid in
acetic acid-acetic anhydride mixture to afford the thiazolopyrimidines 5 which on condensation with aromatic
aldehyde furnish the corresponding arylmethylenethiazolopyrimidine derivatives
6. The product 6 could be prepared directly by the action of chloroacetic acid and
the proper aldehyde on 4 in the
presence of acetic acid-acetic anhydride mixture. Product 2 reacts with malononitrile in the presence of ammonium acetate or
piperidine to afford the pyridine- and pyran- 7 and 8 derivatives,
respectively. Also, compound 1 on
treatment with arylmethylenecyanoacetamide yields the pyridone derivatives 9. Condensation of 1 with malononitrile affords the yliedinemalononitrile 10, which on reaction with p-chlorobenzaldehyde-ammonium acetate or
arylmethylene-cyanoacetamide yields the pyridine derivative 11 (isomer of 8) and the dicarbonitrile derivative 12, respectively. The synthesized compounds have been tested
against three cell lines of human cancer (lung, breast and CNS cancer), and
these compounds show anticancer activity at low concentration as compared to
reference drug 5-fluorodeoxyuridine