Synthesis of multiply arylated pyridines

Takashi Asako; Wakana Hayashi; Kazuma Amaike; Shin Suzuki; Kenichiro Itami; Kei Muto; Junichiro Yamaguchi

doi:10.1016/j.tet.2017.03.095

Synthesis of multiply arylated pyridines

Takashi Asako, Wakana Hayashi, Kazuma Amaike, Shin Suzuki, Kenichiro Itami, Kei Muto, Junichiro Yamaguchi

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

16 Citations (Scopus)

Abstract

We have achieved a synthesis of multiply arylated pyridines by using a [4 + 2] cycloaddition of 2,4-diaryl-5-chloroxazoles and cinnamic acids as a key reaction. The resulting hydroxytriarylpyridines can be derivatized into triarylpyridines, tetraarylpyridines and pentaarylpyridines by sequential cross-couplings. This synthetic method allows for facile and rapid access to highly arylated pyridines with different aryl substituents.

Original language	English
Pages (from-to)	3669-3676
Number of pages	8
Journal	Tetrahedron
Volume	73
Issue number	26
DOIs	https://doi.org/10.1016/j.tet.2017.03.095
Publication status	Published - 2017

Keywords

Cross-coupling
Heterocyclic compound
Palladium
Pyridine
Ring transformation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of multiply arylated pyridines",

abstract = "We have achieved a synthesis of multiply arylated pyridines by using a [4 + 2] cycloaddition of 2,4-diaryl-5-chloroxazoles and cinnamic acids as a key reaction. The resulting hydroxytriarylpyridines can be derivatized into triarylpyridines, tetraarylpyridines and pentaarylpyridines by sequential cross-couplings. This synthetic method allows for facile and rapid access to highly arylated pyridines with different aryl substituents.",

keywords = "Cross-coupling, Heterocyclic compound, Palladium, Pyridine, Ring transformation",

author = "Takashi Asako and Wakana Hayashi and Kazuma Amaike and Shin Suzuki and Kenichiro Itami and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP16H01011, JP16H01140, JP16H04148 (to J.Y.), JP16H07291 (to K.M), the ERATO program from JST (K.I.), and a JSPS research fellowship for young scientists (to K.A. and S.S). We thank Dr. Yasutomo Segawa for assistance with X-ray crystallography. We also thank Dr. Yoshihiro Ishihara (Vertex Pharmaceuticals) for fruitful discussion and critical comments. ITbM is supported by the World Premier International Research Center (WPI) Initiative, Japan.",

year = "2017",

doi = "10.1016/j.tet.2017.03.095",

language = "English",

volume = "73",

pages = "3669--3676",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

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T1 - Synthesis of multiply arylated pyridines

AU - Asako, Takashi

AU - Hayashi, Wakana

AU - Amaike, Kazuma

AU - Suzuki, Shin

AU - Itami, Kenichiro

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP16H01011, JP16H01140, JP16H04148 (to J.Y.), JP16H07291 (to K.M), the ERATO program from JST (K.I.), and a JSPS research fellowship for young scientists (to K.A. and S.S). We thank Dr. Yasutomo Segawa for assistance with X-ray crystallography. We also thank Dr. Yoshihiro Ishihara (Vertex Pharmaceuticals) for fruitful discussion and critical comments. ITbM is supported by the World Premier International Research Center (WPI) Initiative, Japan.

PY - 2017

Y1 - 2017

N2 - We have achieved a synthesis of multiply arylated pyridines by using a [4 + 2] cycloaddition of 2,4-diaryl-5-chloroxazoles and cinnamic acids as a key reaction. The resulting hydroxytriarylpyridines can be derivatized into triarylpyridines, tetraarylpyridines and pentaarylpyridines by sequential cross-couplings. This synthetic method allows for facile and rapid access to highly arylated pyridines with different aryl substituents.

AB - We have achieved a synthesis of multiply arylated pyridines by using a [4 + 2] cycloaddition of 2,4-diaryl-5-chloroxazoles and cinnamic acids as a key reaction. The resulting hydroxytriarylpyridines can be derivatized into triarylpyridines, tetraarylpyridines and pentaarylpyridines by sequential cross-couplings. This synthetic method allows for facile and rapid access to highly arylated pyridines with different aryl substituents.

KW - Cross-coupling

KW - Heterocyclic compound

KW - Palladium

KW - Pyridine

KW - Ring transformation

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