- Reactions of β-Fluorovinamidinium Salt with Bifunctional Hetero Nucleophiles. A New Synthetic Route to Fluorinated Heterocycles
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β-Fluorovinamidium salt (2), readily prepared from N-(2,3,3-trifluoro-1-propenyl) trimethyl-ammonium iodide (1) and diethylamine, reacted with bifunctional hetero nucleophiles such as amidine and guanidine hydrochlorides in the presence of a base to afford regiospecifically monofluoronated pyrimidines 4 in good yields.The one-pot procedure starting from 1 was applicable for synthesizing heterocyclic compounds 4 in almost comparable yields.
- Shi, Xifeng,Ishihara, Takashi,Yamanaka, Hiroki,Gupton, John T.
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p. 1527 - 1530
(2007/10/02)
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- Reactions of 1-Substituted-polyfluoro-1-propenyl p-Toluenesulfonates with Bifunctional Nitrogen Nucleophiles. A New Expedient Access to Monofluorinated Nitrogen Heterocycles
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1-Substituted-2,3,3-trifluoro-1-propenyl p-toluenesulfonates, readily available by the alkylation or arylation of 2,3,3-trifluoro-1-tosyloxy-1-propenyllithium or -zinc reagent, reacted smoothly with amidine or hydrazine derivatives at 70 deg C for 1h to give the corresponding 5-fluoropyrimidine or 4-fluoropyrazole compounds, respectively, in moderate to excellent yields.
- Funabiki, Kazumasa,Ohtsuki, Tetsuya,Ishihara, Takashi,Yamanaka, Hiroki
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p. 239 - 240
(2007/10/02)
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