Facile One-Pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethanesulfonic Anhydride
- 1 September 2004
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 77 (9), 1717-1725
- https://doi.org/10.1246/bcsj.77.1717
Abstract
Iminocarbocation intermediates were in situ-generated by treating various oximes with trifluoromethanesulfonic anhydride (Tf2O) in the presence of triethylamine in toluene and nucleophilic trapping with amines or sodium enolates under mild conditions afforded the corresponding amidines and enamines. Some of the thus-obtained enamines were converted to 2-substituted 4-oxo-3-quinolinecarboxylic acid derivatives by subsequent intramolecular Friedel–Crafts acylation.Keywords
This publication has 22 references indexed in Scilit:
- Facile One-pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethansulfonic AnhydrideChemistry Letters, 2004
- One-Pot Synthesis of N-Imidoylbenzotriazoles via Benzotriazole-Mediated Beckmann Rearrangement of OximesOrganic Letters, 1999
- A useful reagent for the Beckmann rearrangement and the synthesis of nitriles from carboxamides: N,N'-carbonyldiimidazole and reactive halides.CHEMICAL & PHARMACEUTICAL BULLETIN, 1984
- Carbon-carbon bond formation by selective coupling of enol silyl ethers with oxime sulfonatesJournal of the American Chemical Society, 1983
- Organoaluminum-promoted Beckmann rearrangement of oxime sulfonatesJournal of the American Chemical Society, 1983
- Successive Beckmann rearrangement-alkylation sequence by organoaluminum reagents. Simple route to dl-pumiliotoxin CJournal of the American Chemical Society, 1981
- β,β‐Diacyl‐enamine und ‐enole, 9: Zur Darstellung von Aminomethylenderivaten offenkettiger CH2‐acider VerbindungenEuropean Journal of Inorganic Chemistry, 1981
- Studies on Geometric Isomerism by Nuclear Magnetic Resonance. IV. Structure of α-Cyano-β-amino-β-alkylacrylic EstersBulletin of the Chemical Society of Japan, 1967
- Zur Kenntniss der IsonitrosoverbindungenEuropean Journal of Inorganic Chemistry, 1887
- Zur Kenntniss der IsonitrosoverbindungenEuropean Journal of Inorganic Chemistry, 1886