Synthesis of imidazolidinediones and oxazolidinediones from cyclization of propargylureas and propargyl carbamates

A synthetic procedure for the preparation of imidazolidinediones by the base-catalyzed cyclization of propargylureas is described. This method appears to be the most versatile way of obtaining these compounds containing tertiary groups substituted on ring-nitrogen number 3. One of these derivatives,...

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Bibliographic Details
Published inJournal of medicinal chemistry Vol. 22; no. 6; pp. 746 - 748
Main Authors Chiu, Sai-Keung, Keifer, Leonard, Timberlake, Jack W
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.06.1979
Subjects
Animals
Anticonvulsants - chemical synthesis
Carbamates
Cyclization
Electroshock
Imidazoles - chemical synthesis
Imidazoles - pharmacology
Methods
Mice
Oxazoles - chemical synthesis
Oxazoles - pharmacology
Pentylenetetrazole - antagonists & inhibitors
Structure-Activity Relationship
Urea - analogs & derivatives
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Summary:A synthetic procedure for the preparation of imidazolidinediones by the base-catalyzed cyclization of propargylureas is described. This method appears to be the most versatile way of obtaining these compounds containing tertiary groups substituted on ring-nitrogen number 3. One of these derivatives, 3-tert-butyl-5,5-dimethyl-2,4-imidazolidinedione (1a), has shown a moderate level of subcutaneous metrazole seizure threshold activity (scMet indicates potential for control of petit mal epileptic seizures) in control screens on mice, as determined by the National Institute of Neurological and Communicative Disorders and Stroke.
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ark:/67375/TPS-QTSNM8B2-S
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-2623
1520-4804
DOI:10.1021/jm00192a026