Superelectrophilic Activation of N-Aryl Amides of 3-Arylpropynoic Acids: Synthesis of Quinolin-2(1H)-one Derivatives

D.S. Ryabukhin, L.Y. Gurskaya, G.K. Fukin, A.V. Vasilyev

Research output

22 Citations (Scopus)

Abstract

The superelectrophilic activation of N-aryl amides of 3-arylpropynoic acids by Bronsted superacids (CF3SO3H, HSO3F) or strong Lewis acids AlX3 (X = Cl, Br) results in the formation of 4-aryl quinolin-2(1H)-ones in quantitative yields. The vinyl triflates or vinyl chlorides may be formed as additional reaction products. The investigated amides in reactions with benzene give 4,4-diaryl 3,4-dihydroquinolin-2-(1H)-ones under the superelectrophilic activation. 4-Aryl quinolin-2(1H)-ones in POCl3 are converted into 4-aryl 2-chloroquinolines. 4-Fluorophenyl-4-phenyl 3,4-dihydroquinolin-2-(1H)-one give N-formylation products in a yield of 97% under the Vilsmeier-Haack reaction conditions.
Original languageEnglish
Pages (from-to)6428-6443
JournalTetrahedron
Volume70
Issue number37
DOIs
Publication statusPublished - 2014

Fingerprint

Amides
Chemical activation
Derivatives
Vinyl Chloride
Lewis Acids
Acids
Benzene
Reaction products
dihydroquinolin-2(1H)-one
vinyl triflate
2-chloroquinoline

Cite this

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title = "Superelectrophilic Activation of N-Aryl Amides of 3-Arylpropynoic Acids: Synthesis of Quinolin-2(1H)-one Derivatives",
abstract = "The superelectrophilic activation of N-aryl amides of 3-arylpropynoic acids by Bronsted superacids (CF3SO3H, HSO3F) or strong Lewis acids AlX3 (X = Cl, Br) results in the formation of 4-aryl quinolin-2(1H)-ones in quantitative yields. The vinyl triflates or vinyl chlorides may be formed as additional reaction products. The investigated amides in reactions with benzene give 4,4-diaryl 3,4-dihydroquinolin-2-(1H)-ones under the superelectrophilic activation. 4-Aryl quinolin-2(1H)-ones in POCl3 are converted into 4-aryl 2-chloroquinolines. 4-Fluorophenyl-4-phenyl 3,4-dihydroquinolin-2-(1H)-one give N-formylation products in a yield of 97{\%} under the Vilsmeier-Haack reaction conditions.",
keywords = "N-aryl amides of 3-aryl propynoic acids, 4-aryl quinolin-2(1H)-ones, 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones, superacids, superelectrophilic activation",
author = "D.S. Ryabukhin and L.Y. Gurskaya and G.K. Fukin and A.V. Vasilyev",
year = "2014",
doi = "10.1016/j.tet.2014.07.028",
language = "English",
volume = "70",
pages = "6428--6443",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "37",

}

Superelectrophilic Activation of N-Aryl Amides of 3-Arylpropynoic Acids: Synthesis of Quinolin-2(1H)-one Derivatives. / Ryabukhin, D.S.; Gurskaya, L.Y.; Fukin, G.K.; Vasilyev, A.V.

In: Tetrahedron, Vol. 70, No. 37, 2014, p. 6428-6443.

Research output

TY - JOUR

T1 - Superelectrophilic Activation of N-Aryl Amides of 3-Arylpropynoic Acids: Synthesis of Quinolin-2(1H)-one Derivatives

AU - Ryabukhin, D.S.

AU - Gurskaya, L.Y.

AU - Fukin, G.K.

AU - Vasilyev, A.V.

PY - 2014

Y1 - 2014

N2 - The superelectrophilic activation of N-aryl amides of 3-arylpropynoic acids by Bronsted superacids (CF3SO3H, HSO3F) or strong Lewis acids AlX3 (X = Cl, Br) results in the formation of 4-aryl quinolin-2(1H)-ones in quantitative yields. The vinyl triflates or vinyl chlorides may be formed as additional reaction products. The investigated amides in reactions with benzene give 4,4-diaryl 3,4-dihydroquinolin-2-(1H)-ones under the superelectrophilic activation. 4-Aryl quinolin-2(1H)-ones in POCl3 are converted into 4-aryl 2-chloroquinolines. 4-Fluorophenyl-4-phenyl 3,4-dihydroquinolin-2-(1H)-one give N-formylation products in a yield of 97% under the Vilsmeier-Haack reaction conditions.

AB - The superelectrophilic activation of N-aryl amides of 3-arylpropynoic acids by Bronsted superacids (CF3SO3H, HSO3F) or strong Lewis acids AlX3 (X = Cl, Br) results in the formation of 4-aryl quinolin-2(1H)-ones in quantitative yields. The vinyl triflates or vinyl chlorides may be formed as additional reaction products. The investigated amides in reactions with benzene give 4,4-diaryl 3,4-dihydroquinolin-2-(1H)-ones under the superelectrophilic activation. 4-Aryl quinolin-2(1H)-ones in POCl3 are converted into 4-aryl 2-chloroquinolines. 4-Fluorophenyl-4-phenyl 3,4-dihydroquinolin-2-(1H)-one give N-formylation products in a yield of 97% under the Vilsmeier-Haack reaction conditions.

KW - N-aryl amides of 3-aryl propynoic acids

KW - 4-aryl quinolin-2(1H)-ones

KW - 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones

KW - superacids

KW - superelectrophilic activation

U2 - 10.1016/j.tet.2014.07.028

DO - 10.1016/j.tet.2014.07.028

M3 - Article

VL - 70

SP - 6428

EP - 6443

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 37

ER -