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

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-imi...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2020-01, Vol.85 (2), p.1087-1096
Main Authors: Gao, Yu, Zhang, Zhihao, Li, Zhenjiang, Guo, Tianfo, Zhu, Yuejia, Yao, Zhiwei, Liu, Bo, Li, Yongqiang, Guo, Kai
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02992