X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .41. AZOMETHINE YLIDE FORMATION FROM THE REACTIONS OF ALPHA-AMINO-ACIDS AND ESTERS WITH ALLOXAN (STRECKER DEGRADATION) AND WITH 1-PHENYL-3-METHYLPYRAZOLIN-4,5-DIONE
Mf. Aly et al., X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .41. AZOMETHINE YLIDE FORMATION FROM THE REACTIONS OF ALPHA-AMINO-ACIDS AND ESTERS WITH ALLOXAN (STRECKER DEGRADATION) AND WITH 1-PHENYL-3-METHYLPYRAZOLIN-4,5-DIONE, Tetrahedron, 50(3), 1994, pp. 895-906
In situ formation of imines from alpha-amino acids and alloxan or pyra
zolin-45-diones results in decarboxylation forming azomethine ylides w
hich can be trapped as their cycloadducts with maleimides. In the abse
nce of maleimides alloxan gives murexide and the pyrazoline-4,5-diones
give rubazonic acid derivatives. The latter are reformulated as stabl
e azomethine ylides. Methyl glycinate reacts with a pyrazolin-4,5-dion
e and maleimides to give cycloadducts via an ester stabilised azomethi
ne ylide.