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Synthesis of 2‐Trifluoromethyl Quinolines from α,β‐Unsaturated Trifluoromethyl Ketones: Regiochemistry Reversal Comparing to the Standard Skraup‐Doebner‐Von Miller Synthesis
Author(s) -
Pan QianWen,
Wang JunHu,
Wang Qi,
Li HuiJing,
Wu YanChao
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000895
Subject(s) - trifluoromethyl , regioselectivity , chemistry , quinoline , condensation , organic chemistry , trichloroacetic acid , medicinal chemistry , catalysis , alkyl , physics , thermodynamics
Abstract Condensation of α,β‐unsaturated trifluoromethyl ketones with anilines in trichloroacetic acid (TCA) afforded 2‐trifluoromethyl quinolines in moderate to excellent yields, in which a reversal of the regiochemistry of the standard Skraup‐Doebner‐Von Miller quinoline synthesis was achieved. Our endeavors will lead to a better understanding of the controlling elements behind the structural motif.