Synthetic studies on 3-arylquinazolin-4-ones: Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines

Haruhiko Fuwa; Toshitake Kobayashi; Takashi Tokitoh; Yukiko Torii; Hideaki Natsugari

doi:10.1016/j.tet.2005.02.038

Synthetic studies on 3-arylquinazolin-4-ones: Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines

Haruhiko Fuwa, Toshitake Kobayashi, Takashi Tokitoh, Yukiko Torii, Hideaki Natsugari

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

The general synthesis and a novel intramolecular nucleophilic aromatic substitution (S_NAr) reaction of 2-carboxamido-3-arylquinazolin-4- ones, a potentially useful scaffold in the field of medicinal chemistry, are described. The synthetic utility of the S_NAr reaction as a tool for the synthesis of secondary aryl amines, including diaryl amines, is also demonstrated.

Original language	English
Pages (from-to)	4297-4312
Number of pages	16
Journal	Tetrahedron
Volume	61
Issue number	17
DOIs	https://doi.org/10.1016/j.tet.2005.02.038
Publication status	Published - 2005 Apr 25

Keywords

2-Carboxamido-3-arylquinazolin-4-one
Intramolecular reaction
Nucleophilic aromatic substitution
Quinazolinone
Secondary aryl amine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Synthetic studies on 3-arylquinazolin-4-ones: Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines. / Fuwa, Haruhiko; Kobayashi, Toshitake; Tokitoh, Takashi et al.
In: Tetrahedron, Vol. 61, No. 17, 25.04.2005, p. 4297-4312.

Research output: Contribution to journal › Article › peer-review

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abstract = "The general synthesis and a novel intramolecular nucleophilic aromatic substitution (SNAr) reaction of 2-carboxamido-3-arylquinazolin-4- ones, a potentially useful scaffold in the field of medicinal chemistry, are described. The synthetic utility of the SNAr reaction as a tool for the synthesis of secondary aryl amines, including diaryl amines, is also demonstrated.",

keywords = "2-Carboxamido-3-arylquinazolin-4-one, Intramolecular reaction, Nucleophilic aromatic substitution, Quinazolinone, Secondary aryl amine",

author = "Haruhiko Fuwa and Toshitake Kobayashi and Takashi Tokitoh and Yukiko Torii and Hideaki Natsugari",

note = "Funding Information: Continuous support by Takeda Pharmaceutical Company Limited is gratefully acknowledged. ",

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AU - Fuwa, Haruhiko

AU - Kobayashi, Toshitake

AU - Tokitoh, Takashi

AU - Torii, Yukiko

AU - Natsugari, Hideaki

N1 - Funding Information: Continuous support by Takeda Pharmaceutical Company Limited is gratefully acknowledged.

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Y1 - 2005/4/25

N2 - The general synthesis and a novel intramolecular nucleophilic aromatic substitution (SNAr) reaction of 2-carboxamido-3-arylquinazolin-4- ones, a potentially useful scaffold in the field of medicinal chemistry, are described. The synthetic utility of the SNAr reaction as a tool for the synthesis of secondary aryl amines, including diaryl amines, is also demonstrated.

AB - The general synthesis and a novel intramolecular nucleophilic aromatic substitution (SNAr) reaction of 2-carboxamido-3-arylquinazolin-4- ones, a potentially useful scaffold in the field of medicinal chemistry, are described. The synthetic utility of the SNAr reaction as a tool for the synthesis of secondary aryl amines, including diaryl amines, is also demonstrated.

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KW - Nucleophilic aromatic substitution

KW - Quinazolinone

KW - Secondary aryl amine

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Synthetic studies on 3-arylquinazolin-4-ones: Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines

Abstract

Keywords

ASJC Scopus subject areas

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