How 2-anilinovinyl perfluoroalkyl ketones can be mechanistically correlated with their cyclization products 2-(perfluoroalkyl)quinolines
作者： Manfred Schlosser , Holger Keller , Shin-ichi Sumida , Jin Yang
DOI: 10.1016/S0040-4039(97)10304-5
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摘要: When heated in the presence of phosphoryl chloride, 2-anilinovinyl perfluoroalkyl ketones [e.g., 4-anilino-1,1,1-trifluoro-3-buten-2-one] gave 2-(perfluoroalkyl)quinolines 2-(trifluoromethyl)quinoline]. As revealed by cross-over expts., an efficient amine exchange process randomizes structural component final products but not their aminoenone precursors. 1,3-Diaminoallyl cations (vinylogous formidinium salts) are postulated to act as turntables. [on SciFinder (R)]
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sci-hub.se 参考文章(5)
Adrienne Steinacker Dey, Madeleine M. Joullié, Synthesis and properties of fluorine-containing heterocyclic compounds. I. trifluoromethyl quinolines† Journal of Heterocyclic Chemistry. ,vol. 2, pp. 113- 119 ,(1965) , 10.1002/JHET.5570020201
Holger Keller, Manfred Schlosser, 2-(Trifluoromethyl)quinolines from anilines: a novel mode of isomerization and cyclization Tetrahedron. ,vol. 52, pp. 4637- 4644 ,(1996) , 10.1016/0040-4020(96)00168-8
Masaru Hojo, Ryōichi Masuda, Etsuji Okada, Syūhei Sakaguchi, Hitoshi Narumiya, Katsushi Morimoto, O-N, S-N and N-N exchange reactions at olefinic carbon atoms: Facile synthetic method for β-trifluoroacetylvinylamines Tetrahedron Letters. ,vol. 30, pp. 6173- 6176 ,(1989) , 10.1016/S0040-4039(01)93334-9
Russell J. Linderman, Kirollos S. Kirollos, Regioselective synthesis of trifluoromethyl substituted quinolines from trifluoroacetyl acetylenes Tetrahedron Letters. ,vol. 31, pp. 2689- 2692 ,(1990) , 10.1016/S0040-4039(00)94673-2
MAYNARD S. RAASCH, The Chemistry of Sulfur Tetrafluoride. IX. Reaction with Amino Acids in Hydrogen Fluoride1 Journal of Organic Chemistry. ,vol. 27, pp. 1406- 1409 ,(1962) , 10.1021/JO01051A068