20605-43-0Relevant articles and documents
Investigation of Masked N-Acyl-N-isocyanates: Support for Oxadiazolones as Blocked N-Isocyanate Precursors
Gagné-Monfette, William,Vincent-Rocan, Jean-Fran?ois,Lutes, Owen C.,O'Keefe, Geneviève F.,Jeanneret, Alexandria D. M.,Blanger, Claire,Ivanovich, Ryan A.,Beauchemin, André M.
supporting information, p. 14051 - 14056 (2021/09/14)
In contrast to carbon-substituted isocyanates that are common building blocks, N-substituted isocyanates remain underdeveloped and reports on their N-acyl derivatives (i. e. amido-isocyanates) are exceedingly rare. Herein, amido-isocyanates were investiga
Intermolecular aminocarbonylation of alkenes using concerted cycloadditions of iminoisocyanates
Bongers, Amanda,Clavette, Christian,Gan, Wei,Gorelsky, Serge I.,Betit, Lyanne,Lavergne, Kaitlyn,Markiewicz, Thomas,Moon, Patrick J.,Neves, Nicolas Das,Obhi, Nimrat K.,Toderian, Amy B.,Beauchemin, Andrei M.
, p. 1175 - 1194 (2017/11/14)
The aminocarbonylation of alkenes is a powerful method for accessing the β-amino carbonyl motif that remains underdeveloped. Herein, the development of intermolecular aminocarbonylation reactivity of iminoisocyanates with alkenes is presented. This includes the discovery of a fluorenone-derived reagent, which was effective for many alkene classes and facilitated derivatization. Electron-rich substrates were most reactive, and this indicated that the LUMO of the iminoisocyanate is reacting with the HOMO of the alkene. Computational and experimental results support a concerted asynchronous [3 + 2] cycloaddition involving an iminoisocyanate, which was observed for the first time by FTIR under the reaction conditions. The products of this reaction are complex azomethine imines, which are precursors to valuable β-amino carbonyl compounds such as β-amino amides and esters, pyrazolones, and bicyclic pyrazolidinones. A kinetic resolution of the azomethine imines by enantioselective reduction (s = 13.43) allows access to enantioenriched products. Overall, this work provides a new tool to convert alkenes into β-amino carbonyl compounds.
Synthesis of 6-carboxylated phenanthridines by oxidative alkoxycarbonylation-cyclization of 2-isocyanobiphenyls with carbazates
Wang, Gao,Chen, Shan-Yong,Yu, Xiao-Qi
supporting information, p. 5338 - 5341 (2015/01/09)
An iron-catalyzed synthesis of 6-carboxylated phenanthridines starting with readily prepared isocyanides and carbazates was developed. Reactions occurred via addition of alkoxycarbonyl radicals to the isocyanide group and subsequent intramolecular cyclization.