Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides | Health & Environmental Research Online (HERO)

Health & Environmental Research Online (HERO)

Print Feedback Export to File

This record has one attached file:

Citation
Tags

HERO ID

6881178

Reference Type

Journal Article

Title

Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides

Author(s)

Safina, LYu; Selivanova, GA; Koltunov, KYu; Shteingarts, VD; ,

Year

2009

Is Peer Reviewed?

Journal

Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Volume

Issue

Page Numbers

5245-5247

DOI

10.1016/j.tetlet.2009.07.013

Web of Science Id

WOS:000269051700021

Abstract

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF3SO3H) yield 4-phenyl-3,4-dihydi-oquinolin-2-ones, which include a polyfluorinated benzene moiety as a part of the quinoline scaffold. These compounds undergo dehydrophenylation in the presence of AlCl3 to give the Corresponding polyfluoroquinolin-2-ones which are converted into polyfluorinated 2-chloroquinolines on treatment with POCl3. A mechanism for the cyclization reaction presuming the intermediacy of a superelectrophilic O,C-diprotonated form of the starting material is suggested. (C) 2009 Elsevier Ltd. All rights reserved.

Keywords

Polyfluoroanilides; Lewis acid; Superacids; Fluoroquinolinones; Fluoroquinolines; Superelectrophiles