3621-77-0Relevant academic research and scientific papers
Dichloroimidazolidinedione-Activated Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
Gao, Yu,Liu, Jingjing,Li, Zhenjiang,Guo, Tianfo,Xu, Songquan,Zhu, Hui,Wei, Fulan,Chen, Siming,Gebru, Hailemariam,Guo, Kai
, p. 2040 - 2049 (2018)
A novel protocol for the activation of the Beckmann rearrangement utilizing the readily available and economical geminal dichloroimidazolidinediones (DCIDs) on a substoichiometric scale (10 mol %) has been developed. A unique self-propagating mechanism for the substoichiometric dichloroimidazolidinedione-activated transformation was proposed and validated. The substrate scope of the developed protocol has been demonstrated by 23 examples with good to excellent yields (mostly 90-98%) in a short time (mostly 10-30 min), including a substrate for synthesizing the monomer of nylon-12 and a complicated steroidal substrate on a preparative scale. This research not only unveils for the first time the synthetic potential of substoichiometric amounts of dichloroimidazolidinediones in promoting chemical transformation but also offers yet another important illustration of the self-propagating cycle in the context of the Beckmann rearrangement activated by a structurally novel organic promoter.
Electrocatalytic Activation of Donor–Acceptor Cyclopropanes and Cyclobutanes: An Alternative C(sp3)?C(sp3) Cleavage Mode
Brandt, Felix,Jacob, Christoph R.,Jones, Peter G.,Kolb, Simon,Petzold, Martin,Werz, Daniel B.
supporting information, p. 15928 - 15934 (2021/06/21)
We describe the first electrochemical activation of D–A cyclopropanes and D–A cyclobutanes leading after C(sp3)?C(sp3) cleavage to the formation of highly reactive radical cations. This concept is utilized to formally insert molecula
Dichloroimidazolidinedione-activated one-pot Suzuki–Miyaura cross-coupling of phenols
Madankar, Kamelia,Mokhtari, Javad,Mirjafary, Zohreh
, (2020/01/22)
The first general method for the Suzuki-type cross-coupling of phenols with aryl boronic acids using dichloroimidazolidinedione (DCID) as a new reagent is presented. In the presence of DCID and Pd/metal–organic framework (MOF), coupling of aryl boronic acids with a wide range of phenols, was carried out smoothly in tetrahydrofuran (THF) at reflux conditions to afford the cross-coupling products in good to excellent yields. The structures of all compounds were corroborated by 1H- and 13C-NMR. A plausible mechanism for this type of reaction is proposed.
A Novel Modified Cross-Coupling of Phenols and Amines Using Dichloroimidazolidinedione (DCID)
Madankar, Kamelia,Mokhtari, Javad,Mirjafary, Zohreh
supporting information, p. 1725 - 1729 (2020/09/01)
Phenols are considered as an ideal alternative to aryl halides as coupling partners in cross-coupling reactions. In the present work a copper-catalyzed cross-coupling of phenols with various aromatic and aliphatic amines for the synthesis of secondary aryl amines using dichloroimidazolidinedione (DCID) as a new and efficient activating agent has been developed. Substituted phenols were compatible with the standard reaction conditions. The two proposed mechanisms, which are based on the oxidation addition of copper with Ar-OMCID (MCID: Monochloroimidazolidinedione), are also discussed.
Selective synthesis of (Z)-2-enynyl-2-hydroxy-imidazolidine-4,5-diones via Cu(i)-mediated multicomponent coupling of terminal alkynes, carbodiimides and oxalyl chloride
Zhao, Fei,Li, Yuexing,Wang, Yang,Zhang, Wen-Xiong,Xi, Zhenfeng
supporting information, p. 3336 - 3339 (2014/05/20)
(Z)-2-Enynyl-2-hydroxy-imidazolidine-4,5-diones 2 are synthesized for the first time via Cu(i)-mediated (Z)-selective geminal coupling among two molecules of terminal alkynes, carbodiimides, and oxalyl chloride. Further transformation of 2a is performed to yield a highly functionalized spiro heterocyclic compound 5. the Partner Organisations 2014.
Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides
Zhao, Fei,Wang, Yang,Zhang, Wen-Xiong,Xi, Zhenfeng
supporting information; experimental part, p. 6266 - 6270 (2012/09/05)
The one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro- imidazolidindione intermed
