- Ultrafast Click Chemistry with Fluorosydnones
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We report the synthesis and reactivity of 4-fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper-catalyzed and strain-promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ-sydnone PdIIprecursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5-fluoro-1,4-pyrazoles with bimolecular rate constants up to 104m?1s?1, surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4-fluorosydnones was further highlighted by successful radiolabeling with [18F]Selectfluor.
- Liu, Hui,Audisio, Davide,Plougastel, Lucie,Decuypere, Elodie,Buisson, David-Alexandre,Koniev, Oleksandr,Kolodych, Sergii,Wagner, Alain,Elhabiri, Mourad,Krzyczmonik, Anna,Forsback, Sarita,Solin, Olof,Gouverneur, Véronique,Taran, Frédéric
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supporting information
p. 12073 - 12077
(2016/11/16)
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- Novel 6-5 fused ring heterocycle antifolates with potent antitumor activity: Bridge modifications and heterocyclic benzoyl isosters of 2,4-diamino-6,7-dihydro-5H-cyclopenta[d]pyrimidine antifolate
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Structural modifications of an extremely potent inhibitor of dihydrofolate reductase (DHFR) activity and tumor cell growth, N-[4-[3-(2,4-diamino-6,7-dihydro-5H-cyclopenta[d]pyrimidin-5-yl)propyl ]benzoyl]-L-glutamic acid (1), have led to the synthesis of
- Kotake,Okauchi,Iijima,Yoshimatsu,Nomura
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p. 829 - 841
(2007/10/02)
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