Synthesis of Polyfluorinated 4-Phenyl-3,4-Dihydroquinolin-2-ones and Quinolin-2-ones via Superacidic Activation of N-(polyfluorophenyl)cinnamamides | Sciact - CRIS-system of Boreskov Institute of Catalysis

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 : 3 DOI: 10.1016/j.tetlet.2009.07.013

Tags

Fluoroquinolines, Fluoroquinolinones, Lewis acid, Polyfluoroanilides, Superacids, Superelectrophiles

Authors

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

Affiliations

1	N.N. Vorozhtsov Institute of Organic Chemistry, Siberian Division of the Russian Academy of Sciences, 9 Ac. Lavrentjev Avenue, Novosibirsk 630090, Russia
2	G.K. Boreskov Institute of Catalysis, Siberian Division of the Russian Academy of Sciences, 5 Ac. Lavrentjev Avenue, Novosibirsk 630090, Russia
3	Novosibirsk State University, Pirogova Str., 2, Novosibirsk 630090, Russia

Funding (2)

1	Russian Foundation for Basic Research	00-03-40142
2	Russian Foundation for Basic Research	09-03-00248

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF3SO3H) yield 4-phenyl-3,4-dihydroquinolin-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.

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 ANCAN OpenAlex

Submitted:	Apr 22, 2009
Accepted:	Jul 3, 2009
Published online:	Jul 9, 2009
Published print:	Sep 16, 2009

Web of science:	WOS:000269051700021
Scopus:	2-s2.0-67650918373
Elibrary:	13614228
Chemical Abstracts:	2009:905536
Chemical Abstracts (print):	151:403087
OpenAlex:	W1988112731

DB	Citing
Web of science	25
Scopus	25
Elibrary	25
OpenAlex	22