Short Synthesis of Oxetane and Azetidine 3-Aryl-3-carboxylic Acid Derivatives by Selective Furan Oxidative Cleavage.
Maryne A J DuboisMilo A SmithAndrew J P WhiteAlvin Lee Wei JieJames J MousseauChulho ChoiJames A BullPublished in: Organic letters (2020)
Four-membered rings remain underexplored motifs despite offering attractive physicochemical properties for medicinal chemistry. Arylacetic acids bearing oxetanes, azetidines, and cyclobutanes are prepared in two steps: a catalytic Friedel-Crafts reaction from four-membered ring alcohol substrates, followed by mild oxidative cleavage. The suitability of the products as building blocks is reflected in their facile purification and amenability to derivatization. Examples include heteroaromatics and aryltriflates, as well as oxetane-derived profen drug analogues and a new endomorphin derivative containing an azetidine amino acid residue.
Keyphrases
- amino acid
- dna binding
- structure activity relationship
- ms ms
- high performance liquid chromatography
- liquid chromatography tandem mass spectrometry
- molecular docking
- simultaneous determination
- liquid chromatography
- emergency department
- gas chromatography
- mass spectrometry
- reduced graphene oxide
- transcription factor
- highly efficient
- tandem mass spectrometry
- alcohol consumption
- gold nanoparticles
- drug induced
- high resolution
- crystal structure