73708-69-7Relevant academic research and scientific papers
4,5-Dioxo-imidazolinium Cation Activation of 1-Acyl-1-carbamoyl Oximes: Access to Cyanoformamides Using Dichloroimidazolidinedione
Gao, Yu,Guo, Kai,Guo, Tianfo,Li, Yongqiang,Li, Zhenjiang,Liu, Bo,Yao, Zhiwei,Zhang, Zhihao,Zhu, Yuejia
, (2020/01/31)
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.
Solvent-Free Synthesis of Cyanoformamides from Carbamoyl Imidazoles
Nugent, Jeremy,Campbell, Sarah G.,Vo, Yen,Schwartz, Brett D.
, p. 5110 - 5118 (2017/09/23)
A straightforward and solvent-free synthesis of various secondary and tertiary cyanoformamides from carbamoyl imidazoles and TMSCN has been developed. Both cyclic and acyclic carbamoyl imidazoles react smoothly to form the relevant cyanoformamides in excellent yields, often within minutes.
POCl3-mediated reaction of 1-Acyl-1-carbamoyl Oximes: A new entry to cyanoformamides
Yang, Jiming,Xiang, Dexuan,Zhang, Rui,Zhang, Ning,Liang, Yongjiu,Dong, Dewen
supporting information, p. 809 - 811 (2015/03/18)
A facile and efficient one-pot synthesis of cyanoformamides was developed from readily available 1-acyl-1-carbamoyl oximes mediated by phosphoryltrichloride (POCl3) under mild conditions in good to high yields.
Synthesis of cyanoformamides from primary amines and carbon dioxide under mild conditions. Synthesis of ceratinamine
Garcia-Egido, Eduardo,Paz, Jairo,Iglesias, Beatriz,Munoz, Luis
experimental part, p. 3991 - 3999 (2009/12/06)
Treatment of primary amines with tetramethylphenylguanidine (PhTMG) and a cyanophosphonate at -10 °C under an atmosphere of carbon dioxide provides cyanoformamides in very high to excellent yields. The reaction proceeds efficiently within a short time. By
Intramolecular cyanoamidation of unsaturated cyanoformamides catalyzed by palladium: an efficient synthesis of multi-functionalized lactams
Kobayashi, Yusuke,Kamisaki, Haruhi,Takeda, Hiroshi,Yasui, Yoshizumi,Yanada, Reiko,Takemoto, Yoshiji
, p. 2978 - 2989 (2007/10/03)
The Pd(0)-catalyzed intramolecular cyanoamidation of several unsaturated cyanoformamides with alkenyl, allenyl, and alkynyl groups was investigated. In the cases of alkynyl and 1,1-disubstituted alkenyl cyanoformamides, the Pd(0)-catalyzed C-CN activation and subsequent insertion reaction proceeded smoothly and gave the corresponding lactams bearing a cyano group at the β-position in good yields. The mechanism of the reaction was also discussed.
