Simple route to new oxadiazaboroles and oxadiazoles via amidoximes

Abstract

The novel push–pull alkene, the 2-(nitro-nitrosomethylene)-pyrrolidine with numerous aliphatic or aromatic amines as nucleophiles afforded amidoximes. Various substituted oxadiazaborole and oxadiazole derivatives were prepared starting from these amidoximes, widening the synthetic applicability of the push–pull alkenes. Acylation of the amidoximes was also examined. The mechanism of the amidoxime formation was investigated by computational methods.

Graphical Abstract

Keywords:

• Amidoximes
• computational methods
• cyclization
• oxadiazoles
• oxadiazaboroles

Acknowledgments

The authors are indebted to Mrs. Krisztina G. Kara for her technical help.