Synthesis of 2‐Trifluoromethyl Quinolines from α,β‐Unsaturated Trifluoromethyl Ketones: Regiochemistry Reversal Comparing to the Standard Skraup‐Doebner‐Von Miller Synthesis | Zendy

Pan QianWen | Zendy; Wang JunHu | Zendy; Wang Qi | Zendy; Li HuiJing | Zendy; Wu YanChao | Zendy

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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

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.

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