Synthesis of alpha-(4-Oxazolyl)amino Esters via Bronsted Acid Catalyzed Tandem Reaction

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A one-step, Bronsted acid catalyzed tandem reaction for the synthesis of alpha-(4-oxazolyl)amino esters was developed. 4-Nitrobenzenesulfonic acid was found to be an efficient catalyst for the coupling of ethyl 2-oxobut-3-ynoates with amides to provide various a-(4-oxazolyl)amino esters. The experimental and X-ray crystallographic data suggest that a series of bond-forming reactions including imine formation, intermolecular Michael addition, and intramolecular Michael addition are functionalities.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-06
Language
English
Article Type
Article
Keywords

ALPHA-AMINO-ACIDS; GALANIN RECEPTOR AGONIST; PHASE-TRANSFER CATALYSIS; CARBONYL-COMPOUNDS; STRECKER REACTIONS; GENETIC-CODE; DESIGN; BIOCONJUGATION; HETEROCYCLES; KETOESTERS

Citation

ORGANIC LETTERS, v.20, no.11, pp.3319 - 3322

ISSN
1523-7060
DOI
10.1021/acs.orglett.8b01212
URI
http://hdl.handle.net/10203/244042
Appears in Collection
CH-Journal Papers(저널논문)
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