Reactions of 5(4H)-oxazolones with Wittig-Horner reagents: Novel synthesis of dioxopyrrolidinephosphonates and phosphonoalkanoates with anticipated schistosomicidal activity
4-Benzylidene-2-phenyl-5(4H)-oxazolones react with Wittig-Horner reagents in the presence of alcoholic sodium alkoxide to give novel dioxopyrrolidinephosphonates, diethyl [3-(benzoylamino)-1-cyano-2-oxo-4- phenylbut-3-en-1-yl]phosphonate and phosphonoalkenoate derivatives. Both the phosphonate adducts and the ester products were also isolated from the reaction of oxazolones with triethyl phosphonoacetate using alcoholic sodium ethoxide and/or sodium hydride as a base. Possible reaction mechanisms are considered, and the structural assignments are based on analytical and spectroscopic results. The biological evaluation of the new compounds is reported.
Boulos, Leila S.,Arsanious, Mona H. N.,Ewies, Ewies F.,Ramzy, Fatem
experimental part
p. 1211 - 1218
(2009/04/12)
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