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 |
|
||||||
| Affiliations |
|
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.
Cite:
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 OpenAlex
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 OpenAlex
Dates:
| Published print: | Sep 1, 2009 |
Identifiers:
| Web of science: | WOS:000269051700021 |
| Scopus: | 2-s2.0-67650918373 |
| Elibrary: | 13614228 |
| OpenAlex: | W1988112731 |