13715-50-9Relevant academic research and scientific papers
Tf2NH-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles
Zhao, Yingying,Hu, Yancheng,Wang, Chunxiang,Li, Xincheng,Wan, Boshun
, p. 3935 - 3942 (2017/04/11)
An unprecedented Tf2NH-catalyzed formal [3 + 2] cycloaddition of ynamides with dioxazoles was developed to construct various polysubstituted 4-aminooxazoles. This approach features a metal-free catalytic bimolecular assembly of oxazole motifs, a low-cost catalyst, exceptionally mild reaction conditions, a very short reaction time, a broad substrate scope, and high efficiency. This metal-free protocol may find applications in pharmaceutical-oriented synthesis.
Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: Highly efficient synthesis of functionalized oxazoles
Chen, Ming,Sun, Ning,Chen, Haoyi,Liu, Yuanhong
supporting information, p. 6324 - 6327 (2016/05/19)
A gold-catalyzed regioselective [3+2] cycloaddition of ynamides with 1,4,2-dioxazoles was developed and offers a novel approach to obtain highly functionalized oxazoles under mild reaction conditions. 1,4,2-Dioxazole was found to act as an efficient N-acyl nitrene equivalent to trigger a facile generation of α-imino gold-carbene intermediate through the elimination of a ketone.
Sulfur imidations by light-induced ruthenium-catalyzed nitrene transfer reactions
Bizet, Vincent,Bolm, Carsten
supporting information, p. 2854 - 2860 (2015/07/01)
N-Acyl nitrenes have been generated from a range of heterocyclic precursors, and their applications in light-induced ruthenium-catalyzed sulfur imidations have been studied. Analyzing the reaction scope and determining the structural requirements of the in situ formed electrophilic nitrogen species for effective nitrene transfer allowed a mechanistic scheme to be proposed. The mechanistic conclusions were substantiated by the identification of potential intermediates.
Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C-H Amination with a New Type of Amidating Reagent
Park, Yoonsu,Park, Kyung Tae,Kim, Jeung Gon,Chang, Sukbok
supporting information, p. 4534 - 4542 (2015/04/22)
Mechanistic investigations on the CpRh(III)-catalyzed direct C-H amination reaction led us to reveal the new utility of 1,4,2-dioxazol-5-one and its derivatives as highly efficient amino sources. Stepwise analysis on the C-N bond-forming process showed th
5,5-Dimethyl-1,4,2-dioxazoles as versatile aprotic hydroxamic acid protecting groups
Couturier, Michel,Tucker, John L.,Proulx, Caroline,Boucher, Ghislain,Dube, Pascal,Andresen, Brian M.,Ghosh, Arun
, p. 4833 - 4838 (2007/10/03)
5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows α-functionalization.
The photochemistry of acyl azides - IX. Direct and sensitized photolytic generation of acylnitrenes for cycloaddition reactions
Clauss, Kai-Uwe,Buck, Karin,Abraham, Werner
, p. 7181 - 7192 (2007/10/02)
Contrary to ethoxycarbonylnitrene, selective reactions - including cycloadditions - can be carried out with benzoylnitrene. This study analyzes the sequence of reactivity of various bond types with respect to benzoylnitrene, which was generated by three different routes: direct photolysis of benzoyl azide, sensitization of azide decomposition via energy transfer, and photoinduced electron transfer. In all cases the same cycloadducts 23, 24, and 30 were obtained. Carbonyl activity determines the reactivity of unsaturated ketones and aldehydes with respect to benzoylnitrene.
