One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and alpha-bromoketones

A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin- 5-ones from L-amino acid methyl esters, iso-, isothio-or isoselenocyanates, and alpha-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one interm...

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Published inOrganic & biomolecular chemistry Vol. 17; no. 11; pp. 3040 - 3047
Main Authors Haung, Jia-Yun, Barve, Indrajeet J., Sun, Chung-Ming
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 13.03.2019
Royal Society of Chemistry
Subjects
Acids
Amino acids
Chemical synthesis
Chemistry
Chemistry, Organic
Crystallography
Esters
High-performance liquid chromatography
Intermediates
Isocyanates
Liquid chromatography
NMR
Nuclear magnetic resonance
Physical Sciences
Reaction mechanisms
Science & Technology
GFP
GREEN FLUORESCENT PROTEIN
ULTRASOUND
CHROMOPHORES
KAEDE
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Summary:A simple and new multicomponent reaction for the one-pot synthesis of substituted 4-arylidene imidazolin- 5-ones from L-amino acid methyl esters, iso-, isothio-or isoselenocyanates, and alpha-bromoketones is demonstrated. Isolation of thiohydantoin and 5-benzylidene 2-thioxoimidazolidin-4-one intermediates revealed a possible reaction mechanism. The strategy was further extended to the synthesis of 2-iminothiazolines and 2-thioxoimidazolin-4-ones.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob03111h