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

8 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 languageEnglish
JournalTetrahedron
DOIs
Publication statusAccepted/In press - 2017 Jan 31

Fingerprint

Pyridines
Cycloaddition
Cycloaddition Reaction
cinnamic acid

Keywords

  • Cross-coupling
  • Heterocyclic compound
  • Palladium
  • Pyridine
  • Ring transformation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of multiply arylated pyridines. / Asako, Takashi; Hayashi, Wakana; Amaike, Kazuma; Suzuki, Shin; Itami, Kenichiro; Muto, Kei; Yamaguchi, Junichiro.

In: Tetrahedron, 31.01.2017.

Research output: Contribution to journal › Article

Asako, T, Hayashi, W, Amaike, K, Suzuki, S, Itami, K, Muto, K & Yamaguchi, J 2017, 'Synthesis of multiply arylated pyridines', Tetrahedron. https://doi.org/10.1016/j.tet.2017.03.095
Asako T, Hayashi W, Amaike K, Suzuki S, Itami K, Muto K et al. Synthesis of multiply arylated pyridines. Tetrahedron. 2017 Jan 31. https://doi.org/10.1016/j.tet.2017.03.095
Asako, Takashi ; Hayashi, Wakana ; Amaike, Kazuma ; Suzuki, Shin ; Itami, Kenichiro ; Muto, Kei ; Yamaguchi, Junichiro. / Synthesis of multiply arylated pyridines. In: Tetrahedron. 2017.
@article{d973f114e1d14407b92332d650581929,
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",
year = "2017",
month = "1",
day = "31",
doi = "10.1016/j.tet.2017.03.095",
language = "English",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",

}

TY - JOUR

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

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

UR - http://www.scopus.com/inward/record.url?scp=85017164242&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85017164242&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.03.095

DO - 10.1016/j.tet.2017.03.095

M3 - Article

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

ER -

Access to Document