4,5-Dioxo-imidazolinium Cation Activation of 1-Acyl-1-carbamoyl Oximes: Access to Cyanoformamides Using Dichloroimidazolidinedione

Article abstract of DOI:10.1021/acs.joc.9b02992

Cyanoformamides are prevalent as versatile building blocks for accessing synthetically useful intermediates and biologically active compounds. The development of a milder, simpler, and more efficient approach to cyanoformamides is nontrivial. Herein, we demonstrate the effectiveness of 4,5-dioxo-imidazolinium cation activation for transforming 1-acyl-1-carbamoyl oximes to cyanoformamides. By making use of the readily available and highly modifiable dichloroimidazolidinediones (DCIDs), this novel method of activation offers reactivity remarkably greater than that of other reported protocols, exhibits a high functional group compatibility with mild conditions, and could be scaled up easily. More than 30 examples are demonstrated with good to excellent yields in short reaction times. This research not only provides a mild and efficient alternative approach to assembling a portfolio of cyanoformamides but also extends the dichloroimidazolidinedione-mediated chemistry to encompass the C-C bond cleavage reaction.