Alkyl malonamido ester derivatives and their analogues

ABSTRACT

The chemical reactivity of methylene group of I was examined through diazocoupling. IR spectra of the obtained products 1 a-e exclude the possibility of the presence of the diazo tautomer [from a] in equilibrium with the hydrazo tautomer [from b], which is the more stable thermodynamically. The B aminobutyrate 2 was found to exist in equilibrium 2 reversible reaction 2a. Aliphatic aldehydes adds to the NH of the B aminocrotonate tautomer 2a resulting in the corresponding 1,3 oxazine derivatives 3a and b. The alkyl malonamido sugars 4 and 5 was obtained by the direct cylation of II and III, respectively. 4 was easily converted to 3 substituted coumarin 6, while methyl malonamidoaziridine derivative 5 did not. The reactivity of the methylene groups was discussed. The IR and H-NMR data were examined in details