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Mechanochemical Preparation of 3,5-Disubstituted Hydantoins from Dipeptides and Unsymmetrical Ureas of Amino Acid Derivatives
- Source :
- Journal of Organic Chemistry, Journal of Organic Chemistry, American Chemical Society, 2016, 81 (20), pp.9802-9809. ⟨10.1021/acs.joc.6b01832⟩
- Publication Year :
- 2016
- Publisher :
- American Chemical Society (ACS), 2016.
-
Abstract
- International audience; 5-Substituted-3-(alkoxycarbonyl)alkyl-hydantoin derivatives were prepared by mechanochemistry from amino esters or dipeptides, via a 1,1′-carbonyldiimidazole-mediated one-pot/two-step cyclization reaction involving amino acid unsymmetrical urea A and carboxy-imidazolyl-dipeptide ester B intermediates. Comparative experiments in solution were also performed. The successful preparation of an antibacterial agent precursor was also investigated.
- Subjects :
- Hydantoin
010402 general chemistry
01 natural sciences
ball-mill
chemistry.chemical_compound
Dipeptide
Mechanochemistry
Organic chemistry
Antibacterial agent
chemistry.chemical_classification
Amino esters
[CHIM.ORGA]Chemical Sciences/Organic chemistry
010405 organic chemistry
Organic Chemistry
3
5-disubstituted hydantoins
mechanochemistry
carbonyl diimidazole
0104 chemical sciences
Amino acid
chemistry
Urea
CDI
amino acid
Mechanosynthesis
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 81
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....eb00a73718294de0a1de8c936f7bf079
- Full Text :
- https://doi.org/10.1021/acs.joc.6b01832