One-pot synthesis of 3-fluoro-4-(trifluoromethyl)quinolines from pentafluoropropen-2-ol and their molecular modification

The Journal of Organic Chemistry
Tsuyoshi HosokawaKenji Uneyama

Abstract

Pentafluoropropen-2-ol (PFP) was prepared by the reaction of hexafluoroacetone (HFA) with Mg/TMSCl. The one-pot tandem sequential reactions of PFP via Mannich addition with aldimines followed by Friedel-Crafts cyclization and aromatization afforded the title quinolines. A variety of corresponding 3-substituted quinolines were derived from the title quinoline by nucleophilic substitution of 3-fluorine with nucleophiles. A defluorinative transformation of the 4-trifluoromethyl group of the title quinoline with hydrazine afforded pyrazoloquinoline.

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Citations

Jun 13, 2017·Chemical Reviews·Bagher Eftekhari-Sis, Maryam Zirak
Jun 2, 2011·The Journal of Organic Chemistry·Sergey V RyabukhinAndrey A Tolmachev
Nov 26, 2014·Chemical Reviews·Bagher Eftekhari-Sis, Maryam Zirak

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