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

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

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2009, Volume: 50, Number: 37, Pages: 5245-5247 Pages count : DOI: 10.1016/j.tetlet.2009.07.013

Tags

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

Authors

Safina Larisa Yu. ¹ , Selivanova Galina A. ¹ , Koltunov Konstantin Yu. ^2,3 , Shteingarts Vitalij D. ^1,3

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, GK Boreskov Inst Catalysis, Siberian Div, Novosibirsk 630090, Russia
3	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

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.

Safina L.Y. , Selivanova G.A. , Koltunov K.Y. , Shteingarts V.D.
Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides
Tetrahedron Letters. 2009. V.50. N37. P.5245-5247. DOI: 10.1016/j.tetlet.2009.07.013 WOS Scopus РИНЦ

Published print:

Sep 1, 2009

Web of science	WOS:000269051700021
Scopus	2-s2.0-67650918373
Elibrary	13614228
OpenAlex	W1988112731