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2005
Amines
Q 0120
02- 071
Facile One-Pot Syntheses of Amidines and Enamines from Oximes via Beckmann
Rearrangement Using Trifluoromethanesulfonic Anhydride. — Iminocarbocation
intermediates are in situ generated by treatment of various oximes with Tf2O in the
presence of a base. Nucleophilic trapping with sodium enolates (IX) or amines (XI)
under mild conditions affords the corresponding enamines (III), (VIII), (X) and
amidines (XII). Some of the thus-obtained enamines are converted to 2-substituted
4-oxo-3-quinolinecarboxylic acid derivatives, c.g. (XIIII), by subsequent intramolecular Friedel—Crafts acylation. — (TAKUWA, T.; MINOWA, T.; ONISHI, J. Y.;
MUKAIYAMA*, T.; Bull. Chem. Soc. Jpn. 77 (2004) 9, 1717-1725; Kitasato Inst.,
Cent. Basic Res., Kita, Tokyo 114, Japan; Eng.) — M. Paetzel
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