Reaction of N-alpha-acetoxycinnamoyl)-N-hydroxy derivatives of DL-alanine esters. Formation of imidazolidinone and its transformations into pyrrolidinedione and oxazolidinone.

doi:10.1246/BCSJ.42.228

Paper

Reaction of N-alpha-acetoxycinnamoyl)-N-hydroxy derivatives of DL-alanine esters. Formation of imidazolidinone and its transformations into pyrrolidinedione and oxazolidinone.

Published 1969 · Y. Chigira, M. Masaki, M. Ota

Bulletin of the Chemical Society of Japan

Q2 SJR score

0

Citations

0

Influential Citations

Full textSemantic Scholar

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.

Study Snapshot

N-(-acetoxycinnamoyl)-N-hydroxy derivatives of DL-alanine esters can be used to form imidazolidinone and its transformations into pyrrolidinedione and oxazolidinone.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Reaction of N-alpha-acetoxycinnamoyl)-N-hydroxy derivatives of DL-alanine esters. Formation of imidazolidinone and its transformations into pyrrolidinedione and oxazolidinone.

Sign up to use Study Snapshot

References

Heilmittelchemische Studien in der heterocyclischen Reihe. 12. Mitteilung. Synthese von 4‐Oxazolidonen aus Diacetyl und Ketoncyanhydrinen. Vergleichende Untersuchung der IR.‐Absorptionsspektren

This study successfully synthesized 4-oxazolidones from diacetyl and ketoncyanhydrines, confirming their structure through chemical transformation and infrared spectrum comparison.

Citations