Sc(OTf)3-Mediated One-Pot Synthesis of 3,4-Disubstituted 1H-Pyrazoles and 3,5-Disubstituted Pyridines from Hydrazine or Ammonia with Epoxides.

Here, we report the synthesis of 3,4-disubstituted 1H-pyrazoles and 3,5-disubstituted pyridines from the reaction of epoxides with hydrazine and ammonia, respectively. Both reactions utilize Sc(OTf)3 as a Lewis acid. The pyrazole synthesis utilizes N-bromosuccinimide to convert the intermediate pyrazolines to the pyrazoles, whereas the pyridine synthesis utilizes FeCl3 as a cocatalyst.

Sc(OTf)3-Mediated One-Pot Synthesis of 2,3-Disubstituted Quinolines from Anilines and Epoxides.

Here, we report the first synthesis of 2,3-disubstituted quinolines from anilines and aromatic or aliphatic epoxides. This reaction utilizes Sc(OTf)3 as a Lewis acid and TEMPO as an oxygen scavenger. A wide variety of highly substituted quinolines were obtained with moderate to excellent yields (up to 96%).

Diastereoselective One-Pot Synthesis of Oxazolines Using Sulfur Ylides and Acyl Imines.

This work describes an extended version of the Corey-Chaykovsky reaction to access oxazolines using sulfur ylides and stable precursors of acyl imines. The reaction proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxazolines following in situ Heine-type aziridine ring expansion upon treatment with BF3·OEt2. Following the same one-pot procedure, amidine imides react with the sulfur ylides to provide imidazolines.