- PARTIALLY FLUORINATED HETEROCYCLIC COMPOUNDS. PART 19. THE FORMATION OF FISCHER INDOLE PRODUCTS FROM A SERIES OF HYDRAZONES DERIVED FROM PENTAFLUOROPHENYLHYDRAZINE AND 1,3,4,5,6,7,8-HEPTAFLUORO-2-NAPHTHYLHYDRAZINE. THE SURPRISING LOSS OF o-FLUORINE
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The pentafluorophenyl and 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazones of a variety of aldehydes and ketones give 4,5,6,7-tetrafluoroindole and 4,5,6,7,8,9-hexafluorobenzindole derivatives when heated under reflux in tetralin.These products are typic
- Benke, Frank D.,Brooke, Gerald M.
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- The synthesis of 7,8,9,10-Tetrafluoroellipticine
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We have synthesized a novel ellipticine analogue, 7,8,9,10-Tetrafluoroellipticine, in nine steps from hexafluorobenzene and ethyl cyanoacetate, via 1-(phenysulfonyl)-4,5,6,7-Tetrafluoroindole. The key step is lithiation of the indole and subsequent coupling with 3,4-pyridinedicarboxylic acid anhydride to afford a ketolactam. Reaction of the lactam with methyllithium followed by reduction with sodium borohydride yields 7,8,9,10-Tetrafluoroellipticine. formula presented.
- James Gruver,Onyango, Evans O.,Gribble, Gordon W.
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p. 144 - 152
(2018/07/05)
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- Synthesis of indoles with a polyfluorinated benzene ring
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A two-step sequence consisting of a Sonogashira coupling of polyfluorinated 2-iodoanilines with terminal alkynes, followed by a KOH promoted cyclization of the 2-alkynylanilines thus formed, has been developed as a one-pot synthesis of 2-R-indoles (R=n-Bu
- Politanskaya, Larisa V.,Chuikov, Igor P.,Shteingarts, Vitalij D.
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p. 8477 - 8486
(2013/09/02)
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- Polyfluoroaralkylamines: an improved synthesis of 4,5,6,7-tetrafluoroindole
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Tetrafluoroindole (5), a precursor for potential biologically-active compounds, was prepared previously in a four-step synthesis from C6F6.However, catalytic reduction of pentafluorophenylacetonitrile (2) to 2-pentafluorophenylethyl amine (3) is accompanied by a significant amount of a secondary amine, which, like 3, undergoes cyclization to an indoline and subsequent dehydrogenation to a new indole 8.The side-reaction in the reduction of 2 to 3 is obviated by the use of LiAlH4/AlCl3 (1:1).The final aromatization to yield 5 is vastly improved by replacing MnO2 with DDQ. - Keywords: Polyfluoroaralkylamines; Synthesis; Tetrafluoroindole; NMR spectroscopy; IR spectroscopy
- Filler, Robert,Chen, Wei,Woods, Sarah M.
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