10.1021/acs.joc.9b02992.s001
Yu Gao
Yu
Gao
Zhihao Zhang
Zhihao
Zhang
Zhenjiang Li
Zhenjiang
Li
Tianfo Guo
Tianfo
Guo
Yuejia Zhu
Yuejia
Zhu
Zhiwei Yao
Zhiwei
Yao
Bo Liu
Bo
Liu
Yongqiang Li
Yongqiang
Li
Kai Guo
Kai
Guo
4,5-Dioxo-imidazolinium
Cation Activation of 1‑Acyl-1-carbamoyl
Oximes: Access to Cyanoformamides Using Dichloroimidazolidinedione
American Chemical Society
2019
building blocks
cyanoformamide
group compatibility
DCID
modifiable dichloroimidazolidinediones
reaction times
30 examples
Dichloroimidazolidinedione Cyanoformamides
dichloroimidazolidinedione-mediated chemistry
1- acyl -1-carbamoyl oximes
activation
alternative approach
novel method
accessing synthetically
2019-12-31 13:38:01
Journal contribution
https://acs.figshare.com/articles/journal_contribution/4_5-Dioxo-imidazolinium_Cation_Activation_of_1_Acyl-1-carbamoyl_Oximes_Access_to_Cyanoformamides_Using_Dichloroimidazolidinedione/11482212
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.