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Synthesis of 4‐Oxo‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazole‐3‐carboxylic Acid Esters
- Source :
- Synthetic Communications. 34:1617-1623
- Publication Year :
- 2004
- Publisher :
- Informa UK Limited, 2004.
-
Abstract
- 3‐Imidazoline 3‐oxides react regioselectively with 3‐phenylpropanoic acid alkyl esters to give the corresponding 2‐phenyl‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazole‐3‐carboxylic acid alkyl esters. This adducts convert to imidazole and the corresponding alkyl 3‐oxo‐3‐phenylpropanoic acid esters when treated with alkoxides or heated under vacuum. Attempts to oxidise the carbon–carbon double bond using KMnO4–FeSO4 led to the formation of heretofore unknown 4‐oxo‐3a,4,5,6‐tetrahydroimidazo[1,5‐b]isoxazoles.
- Subjects :
- Vacuum
Unclassified drug
Double bond
Carboxylic acid
Adducts
Nitrones
Heterocycles
3 imidazoline 3 oxide
Ferrous sulfate
Medicinal chemistry
Article
Adduct
Regio
Heating
Synthesis
chemistry.chemical_compound
Direct
Hydroxylamines
Oxidation
Imidazole
Organic chemistry
Chemical bond
Isoxazole
Chemistry, organic
Propionic acid derivative
Alkyl
Imidazole derivative
chemistry.chemical_classification
Heterocyclic compound
4 oxo 3a,4,5,6 tetrahydroimidazo[1,5 b]isoxazole 3 carboxylic acid ester
Permanganate potassium
Organic Chemistry
3 phenylpropanoic acid ester
Carboxylic acid derivative
General Medicine
Carbon
Chemistry
Imidazoline 3-oxides
chemistry
3 oxo 3 phenylpropanoic acid ester
1,3-dipolar cycloaddition
Diastereoselective addition
Subjects
Details
- ISSN :
- 15322432 and 00397911
- Volume :
- 34
- Database :
- OpenAIRE
- Journal :
- Synthetic Communications
- Accession number :
- edsair.doi.dedup.....b8ce6e3b4c83ef663eb5672bc16d3bcb