Paper
Reaction of N-alpha-acetoxycinnamoyl)-N-hydroxy derivatives of DL-alanine esters. Formation of imidazolidinone and its transformations into pyrrolidinedione and oxazolidinone.
Published Jan 1, 1969 · DOI · Y. Chigira, M. Masaki, M. Ota
Bulletin of the Chemical Society of Japan
0
Citations
0
Influential Citations
Abstract
Treatment of N-benzyloxy-DL-alanine ethyl ester (I) with α-acetoxycinnamoyl chloride (II) gave N-(α-acetoxycinnamoyl)-N-benzyloxy-DL-alanine ethyl ester (III), which was treated with aqueous sodium bicarbonate, piperidine or hydroxylamine to afford N-benzyloxy-N-(phenyl-pyruvoyl)-DL-alanine ethyl ester (IV). Reaction of III or IV with ammonia afforded 5-benzylidene-2-methyl-4-oxo-2-imidazolidinecarboxylic acid (V), which was transformed into 5-methyl-4-phenyl-2,3-pyrrolidinedione (VI) by treatment with aqueous sodium hydroxide and into methyl 5-benzylidene-2-methyl-4-oxo-2-oxazolidinecarboxylate (VII) by treatment with methanolic hydrogen chloride. VI was also derived from III or IV by treatment with sodium hydroxide. N-(α-Acetoxycinnamoyl)-N-hydroxy-DL-alanine t-butyl ester prepared from N-hydroxy-DL-alanine t-butyl ester and II, was treated with aqueous sodium hydroxide to give t-butyl 5-benzylidene-2-methyl-4-oxo-2-oxazolidinecarboxylate.
N-(-acetoxycinnamoyl)-N-hydroxy derivatives of DL-alanine esters can be used to form imidazolidinone and its transformations into pyrrolidinedione and oxazolidinone.
Full text analysis coming soon...