Dimroth rearrangement to 2-N-alkylated amino pyridines: an unusual reaction of primary amines with ylidineketonitriles

Abstract

Unusual reaction of Ylideneketonitrile with primary amine led to the formation of 2-N-alkylated-3,5-trisubstituted pyridines. Mechanistic aspect of the reaction path was mapped by isolation and characterization of crucial intermediates of the reaction. Dimroth rearrangement was key to the formation of diverse pyridine derivatives in good to excellent yield (50 − 90%).

Graphical Abstract

Keywords:

• Pyridines
• Dimroth rearrangement
• Ylidineketonitriles

Acknowledgements

The authors would like to thank Syngenta Biosciences Pvt. Ltd. Goa for providing opportunity to Damodar K and Mahesh K carry out the above work as part of their PhD under the corporate PhD program.

Supporting information

Full experimental details, ¹H and 13C NMR spectra, UV data and X-Ray analysis. This material can be found via the “Supplementary Content” section of this article’s webpage.