Facile one-pot synthesis of 2,3,5-substituted 1,2,4-oxadiazolines from nitriles in aqueous solution.
[reaction: see text] Alkyl/aryl amidoximes, prepared from the corresponding nitriles and N-alkylhydroxylamines, have readily undergone consecutive Michael additions to electron-deficient alkynes and provided highly substituted 1,2,4-oxadiazolines in good yields in homogeneous aqueous solution.
Naidu
B Narasimhulu
BN
The Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, Connecticut 06422, USA. narasimhulu.naidu@bms.com
Sorenson
Margaret E
ME
D000480:Alkynes / Q000138:chemical synthesis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010069:Oxadiazoles / Q000138:chemical synthesis*; D010091:Oximes / Q000138:chemical synthesis; D012996:Solutions; D014867:Water / Q000737:chemistry
D000480:Alkynes; D009570:Nitriles; D010069:Oxadiazoles; D010091:Oximes; D012996:Solutions; D014867:Water