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Note | Regular issue | Vol 78, No. 1, 2009, pp.213-220
Published online, 22nd September, 2008
DOI: 10.3987/COM-08-11519
A Synthetic Application of β-Aminoalanines to Some New 5-Dialkylaminomethyl-3-phenylhydantoin Derivatives

Fumiko Fujisaki, Kaori Shoji, and Kunihiro Sumoto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

5-Dialkylaminomethylhydantoins (3) were synthesized from β-aminoalanines (1) as the starting materials in two stages. Intermediate urea derivatives (2) prepared from the addition reaction of β-aminoalanines to phenyl isocyanate are easily cyclized to 5-dialkylaminomethylhydantoins (3) with good yields. The deamination reaction of some of the hydantoin derivatives (3a, 3b) in water were observed and resulted in the formation of 3-phenyl-5-methylenehydantoin (4). The hydantoin derivative (3b) regenerated a urea derivative (2c, d) by treatment with excess amounts of pyrrolidine or piperidine.