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

School of Advanced Science and Engineering

Research output: Contribution to journal › Article

12 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
Journal	Tetrahedron
DOIs	https://doi.org/10.1016/j.tet.2017.03.095
Publication status	Accepted/In press - 2017 Jan 31

Keywords

Cross-coupling
Heterocyclic compound
Palladium
Pyridine
Ring transformation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Asako, T., Hayashi, W., Amaike, K., Suzuki, S., Itami, K., Muto, K., & Yamaguchi, J. (Accepted/In press). Synthesis of multiply arylated pyridines. Tetrahedron. https://doi.org/10.1016/j.tet.2017.03.095

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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

PY - 2017/1/31

Y1 - 2017/1/31

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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.

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KW - Heterocyclic compound

KW - Palladium

KW - Pyridine

KW - Ring transformation

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