15132-01-1Relevant academic research and scientific papers
1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation
Wang, Ye,Zheng, Lei,Shi, Xiaodong,Chen, Yunfeng
, p. 886 - 889 (2021/02/01)
Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.
Exploiting Synergistic Catalysis for an Ambient Temperature Photocycloaddition to Pyrazoles
Lakeland, Christopher P.,Watson, David W.,Harrity, Joseph P. A.
, p. 155 - 159 (2019/12/11)
Sydnone-based cycloaddition reactions are a versatile platform for pyrazole synthesis, however they operate under harsh conditions (high temperature and long reaction times). Herein we report a strategy that addresses this limitation utilizing the synergistic combination of organocatalysis and visible-light photocatalysis. This new approach proceeds under ambient conditions and with excellent levels of regiocontrol. Mechanistic studies suggest that photoactivation of sydnones, rather than enamines, is key to the successful implementation of this process.
Cu-catalysed pyrazole synthesis in continuous flow
Comas-Barceló, Júlia,Blanco-Ania, Daniel,Van Den Broek, Sebastiaan A. M. W.,Nieuwland, Pieter J.,Harrity, Joseph P. A.,Rutjes, Floris P. J. T.
, p. 4718 - 4723 (2016/07/07)
The synthesis of 1,4-disubstituted pyrazoles via the cycloaddition reaction of sydnones and terminal alkynes has been achieved employing silica-supported copper catalysts. Furthermore, this methodology has been successfully implemented in continuous flow
Cu-promoted sydnone cycloadditions of alkynes: Scope and mechanism studies
Comas-Barcel?3, Jffllia,Foster, Robert S.,Fiser, B??la,Gomez-Bengoa, Enrique,Harrity, Joseph P. A.
, p. 3257 - 3263 (2015/03/05)
Cu salts have been found to promote the cycloaddition reaction of sydnones and terminal alkynes, providing significant reduction in reaction times. Specifically, the use of Cu(OTf)2 is found to provide 1,3-disubstituted pyrazoles, whereas simpl
One-pot synthesis of 1,4-disubstituted pyrazoles from arylglycines via copper-catalyzed sydnone-alkyne cycloaddition reaction
Specklin, Simon,Decuypere, Elodie,Plougastel, Lucie,Aliani, Soifia,Taran, Frédéric
, p. 7772 - 7777 (2014/10/15)
A robust method for constructing 1,4-pyrazoles from arylglycines was developed using the copper-catalyzed sydnone-alkyne cycloaddition reaction. The procedure offers a straightforward and general route to the pyrazole heterocycle through a three-step one-pot procedure.
Discovery of chemoselective and biocompatible reactions using a high-throughput immunoassay screening
Kolodych, Sergii,Rasolofonjatovo, Evelia,Chaumontet, Manon,Nevers, Marie-Claire,Creminon, Christophe,Taran, Frederic
, p. 12056 - 12060 (2013/12/04)
An immunoassay-based method was used to screen numerous combinations of dipoles and dipolarophiles for their ability to undergo chemoselective and biocompatible [3+2] cycloaddition reactions. The approach fulfills most of the requirements of the click concept and led to the discovery of a copper-catalyzed reaction that generates pyrazoles from sydnone and alkyne reagents. Copyright
Regioselectivity studies of sydnone cycloaddition reactions of azine-substituted alkynes
Foster, Robert S.,Jakobi, Harald,Harrity, Joseph P.A.
experimental part, p. 1506 - 1508 (2011/05/16)
The synthesis of azine-substituted pyrazoles by a sydnone cycloaddition strategy is described. Incorporation of a 3-pyridyl moiety at the sydnone N-atom has little effect on either reactivity or regioselectivity, however, 2-ethynyl-pyridine and -pyrimidin
Pyrazole synthesis using a titanium-catalyzed multicomponent coupling reaction and synthesis of withasomnine
Majumder, Supriyo,Gipson, Kevin R.,Staples, Richard J.,Odom, Aaron L.
experimental part, p. 2013 - 2023 (2011/02/28)
The titanium-catalyzed 3-component coupling of an alkyne, isonitrile, and amine can be used to generate tautomers of 1,3-diimines. These diimines produced in situ undergo cyclization with hydrazine and hydrazine derivatives in a one-pot procedure to provi
SYNTHESIS AND REACTION OF TRIBUTYLSTANNYLPYRAZOLES
Sakamoto, Takao,Shiga, Futoshi,Uchiyama, Daishi,Kondo, Yoshinori,Yamanaka, Hiroshi
, p. 813 - 818 (2007/10/02)
1,3-Dipolar cycloaddition reaction of diazomethane and ethyl diazoacetate with tributylstannylacetylenes occurred regioselectively to afford the corresponding 3(5)-tributylstannylpyrazoles.The cycloaddition reaction of 3-phenylsydnone with the stannylacetylenes proceeded also regioselectively, and 3-tributylstannyl-1-phenylpyrazoles were isolated. 4-Tributylstannyl- and 5-tributylstannyl-1-phenylpyrazole were prepared by the stannylation of 4-lithio- and 5-lithio-1-phenylpyrazoles with tributylstannyl chloride.Iodination, benzoylation, and phenylation of the stannylpyrazoles were examined.
