Ring-Substituted α-Amino Acids. I. The Michael-type Addition of Maleic Hydrazide and Related Compounds leading to the α-Amino Acids.

Abstract

The Michael-type addition of maleic and phthalic hydrazide derivatives with an α, β-unsaturated carbonyl compound such as methyl vinyl ketone or acrolein was examined. All of the products were comfirmed to be the N-addition products by comparing their infrared spectra with those of the corresponding O-and N-deuterated compounds. By the Bucherer synthesis these addition products were converted to the corresponding hydantoins from which new, heterocyclic ring-substituted α-amino acids were obtained by hydrolyzing with barium hydroxide. Some of the hydantoins were independently synthesized from 2-amino-2-methyl-4-hydroxybutyric acid via 4-(2-iodoethyl)-4-methylimidazolidine-2, 5-dione.