13183-08-9Relevant academic research and scientific papers
Synthesis of aminopyrazoles from sydnones and ynamides
Wezeman,Comas-Barceló,Nieger,Harrity,Br?se
, p. 1575 - 1579 (2017)
Aminopyrazoles are prepared from readily accessible sydnones and sulfonyl ynamides using either a copper-mediated sydnone alkyne cycloaddition (CuSAC) or in situ generated strained cyclic ynamides.
Anionic N-heterocyclic carbenes by decarboxylation of sydnone-4-carboxylates
Lücke, Ana-Luiza,Wiechmann, Sascha,Freese, Tyll,Nieger, Martin,F?ldes, Tamás,Pápai, Imre,Gjikaj, Mimoza,Adam, Arnold,Schmidt, Andreas
, p. 2092 - 2099 (2018/03/26)
Unstable N-heterocyclic carbenes can be masked and stabilized as pseudo-cross-conjugated hetarenium-carboxylates which decarboxylate on warming. This study deals with the decarboxylation of carboxylates of mesoionic compounds to generate anionic N-heteroc
Expanding available pyrazole substitution patterns by sydnone cycloaddition reactions
Brown,Harrity
, p. 3160 - 3172 (2017/05/08)
We report the use of alkynylsilanes for the regiocontrolled synthesis of pyrazoles from functionalised sydnones. The strategies outlined herein allow a range of pyrazoles to be accessed with substitution patterns that are otherwise not directly obtained with high selectivity by alkyne cycloadditions. Moreover, this study serendipitously highlighted a simple and convenient procedure for the synthesis of aryl monofluoromethyl ethers through the combination of TBAF and dichloromethane.
A Mild and Regiospecific Synthesis of Pyrazoleboranes
Brown, Andrew W.,Comas-Barceló, Júlia,Harrity, Joseph P. A.
supporting information, p. 5228 - 5231 (2017/04/24)
Alkynylboranes show unprecedented reactivity in their [4+2] cycloaddition of sydnones offering access to fully substituted pyrazoles within a few hours at room temperature. This method delivers synthetically valuable pyrazoleboranes with complete control of regioselectivity, and these intermediates can be further elaborated through functionalization of the C?B bond.
