F. Ramirez, S. Bhatia, C. D. Telefus
1969
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron
Abstract
Abstract The 2,2,2-trimethoxy-4,5-dimethyl-2,2-dihydro-1,3,2-dioxaphospholene made from biacetyl and trimethyl phosphite reacted with one mole equiv. of para-substituted phenylisocyanates to give 2,2,2-trimethoxy-4-(p-substituted)phenylimino-5-acetyl-5-methyl-2,2-dihydro-1,3,2-dioxaphospholanes. The latter reacted with another mole of isocyanate and gave 1,3-diaryl-5-acetyl-5-methyl-hydantoins, precursors of β-keto-α-amino acids. The phenylglyoxal-trimethyl phosphite adduct gave a tautomeric form of the 5-benzoyl-hydantoin. The phenylglyoxal-trimethyl phosphite adduct reacted with one mole equiv of aroyl- and acyl-isocyanates and yielded 2-aryl- or 2-alkyl-5-benzoyl-4-hydroxyoxazoles, the tautomers of 4-oxazolones and the precursors of β-keto-α-hydroxyacid amides. The 4-methoxyoxazoles were made from the 4-hydroxyoxazoles and diazomethane.