Phosphorylnitrile oxides. 6. 1,3-cycloaddition with azomethines and nitriles

Abstract

The 1,3-dipolar cycloaddition of diisopropoxyphosphorylnitrile oxide to Schiff bases gives 3-diisopropoxyphosphoryl-4-R-5-phenyl-1,2,4-oxadiazolines. The cycloaddition of phosphorylated nitrile oxides at the azomethine bond of hydrazones does not proceed due to the low dipolarophilic activity of the CH = N bond and high tendency of phosphorylnitrile oxidesto undergo dimerization and polymerization. The reaction of nitrile oxides with 2-hydroxybenzylidenaniline leads to the corresponding ester of diisopropoxyphosphorylformhydroxamic acid. The nitrile group undergoes cycloaddition only when activated. The reaction of a solution of phosphorylnitrile oxides in benzene with tetracyanoethylene gives the bisadduct at the two C = N bonds without affecting the C = C bond.

How to Cite
Pavlov, V. A.; Kurdyukov, A. I.; Moskva, V. V. Chem. Heterocycl. Compd. 1994, 30, 1095. [Khim. Geterotsikl. Soedin. 1994, 1261.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01171173