274917-70-3Relevant academic research and scientific papers
Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation
Del Vecchio, Antonio,Talbot, Alex,Caillé, Fabien,Chevalier, Arnaud,Sallustrau, Antoine,Loreau, Olivier,Destro, Gianluca,Taran, Frédéric,Audisio, Davide
supporting information, p. 11677 - 11680 (2020/10/19)
A general procedure for the late-stage [11C], [13C] and [14C]carbon isotope labeling of cyclic carbamates is reported. This protocol allows the incorporation of carbon dioxide, the primary source of carbon-14 and carbon-11 radioisotopes, in a direct, cost-effective and sustainable manner. A disconnection/reconnection strategy, involving ring opening/isotopic closure, was also implemented.
Metal free carboamination of internal alkynes - An easy access to polysubstituted quinolines
Stopka,Niggemann
supporting information, p. 5761 - 5764 (2016/05/19)
A metal free carboamination of unactivated alkynes towards highly substituted quinolines was realized in the presence of a synergistic Br?nsted acid catalyst system. Supported by mechanistic probes, the reaction proceeds via a highly reactive vinyl cation in a C-C bond formation - Schmidt reaction sequence. The irreversible extrusion of N2, as a powerful driving force, allows for a general conversion of poorly nucleophilic aliphatic alkynes.
A simple route to polysubstituted indoles exploiting azide induced furan ring opening
Abaev, Vladimir T.,Plieva, Anastasiya T.,Chalikidi, Petrakis N.,Uchuskin, Maxim G.,Trushkov, Igor V.,Butin, Alexander V.
supporting information, p. 4150 - 4153 (2014/09/30)
A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.
Highly efficient induction of chirality in intramolecular [2 + 2] cycloadditions between ketenimines and imines
Cossio, Fernando P.,Arrieta, Ana,Lecea, Begona,Alajarin, Mateo,Vidal, Angel,Tovar, Fulgencio
, p. 3633 - 3641 (2007/10/03)
Highly stereocontrolled, intramolecular [2 + 2] cycloadditions between ketenimines and imines leading to 1,2-dihydroazeto[2,1-b]quinazolines have been achieved. The source of stereocontrol is a chiral carbon atom adjacent either to the iminic carbon or nitrogen atom. In the first case, the stereocontrol stems from the preference for the axial conformer in the first transition structure. In the second case, the origin of the stereocontrol lies on the two-electron stabilizing interaction between the C-C bond being formed and the σ* orbital corresponding to the polar C-X bond, X being an electronegative atom. These models can be extended to other related systems for predicting the stereochemical outcome in this intramolecular reaction.
