Synthesis of heteroarylazulenes: transition metal free coupling strategy of azulene with heterocycles

Taku Shoji; Ryuji Yokoyama; Shunji Ito; Masataka Watanabe; Kozo Toyota; Masafumi Yasunami; Noboru Morita

doi:10.1016/j.tetlet.2006.12.083

Synthesis of heteroarylazulenes: transition metal free coupling strategy of azulene with heterocycles

Taku Shoji, Ryuji Yokoyama, Shunji Ito, Masataka Watanabe, Kozo Toyota, Masafumi Yasunami, Noboru Morita

SCI - Chemistry

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

36 Citations (Scopus)

Abstract

Azulene reacts with highly electrophilic trifluoromethanesulfonates of N-containing heterocycles to give 1-dihydroheteroaryl and 1,3-bis(dihydroheteroaryl)azulene derivatives in a good yield. Treatment of the dihydroheteroarylazulene derivatives with KOH or tert-BuOK afforded 1-heteroaryl and 1,3-bis(heteroaryl)azulenes in a good yield.

Original language	English
Pages (from-to)	1099-1103
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2006.12.083
Publication status	Published - 2007 Feb 12

Keywords

Azulene
Electrophilic substitution
Heterocycle

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10.1016/j.tetlet.2006.12.083

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title = "Synthesis of heteroarylazulenes: transition metal free coupling strategy of azulene with heterocycles",

abstract = "Azulene reacts with highly electrophilic trifluoromethanesulfonates of N-containing heterocycles to give 1-dihydroheteroaryl and 1,3-bis(dihydroheteroaryl)azulene derivatives in a good yield. Treatment of the dihydroheteroarylazulene derivatives with KOH or tert-BuOK afforded 1-heteroaryl and 1,3-bis(heteroaryl)azulenes in a good yield.",

keywords = "Azulene, Electrophilic substitution, Heterocycle",

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T1 - Synthesis of heteroarylazulenes

T2 - transition metal free coupling strategy of azulene with heterocycles

AU - Shoji, Taku

AU - Yokoyama, Ryuji

AU - Ito, Shunji

AU - Watanabe, Masataka

AU - Toyota, Kozo

AU - Yasunami, Masafumi

AU - Morita, Noboru

PY - 2007/2/12

Y1 - 2007/2/12

N2 - Azulene reacts with highly electrophilic trifluoromethanesulfonates of N-containing heterocycles to give 1-dihydroheteroaryl and 1,3-bis(dihydroheteroaryl)azulene derivatives in a good yield. Treatment of the dihydroheteroarylazulene derivatives with KOH or tert-BuOK afforded 1-heteroaryl and 1,3-bis(heteroaryl)azulenes in a good yield.

AB - Azulene reacts with highly electrophilic trifluoromethanesulfonates of N-containing heterocycles to give 1-dihydroheteroaryl and 1,3-bis(dihydroheteroaryl)azulene derivatives in a good yield. Treatment of the dihydroheteroarylazulene derivatives with KOH or tert-BuOK afforded 1-heteroaryl and 1,3-bis(heteroaryl)azulenes in a good yield.

KW - Azulene

KW - Electrophilic substitution

KW - Heterocycle

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SP - 1099

EP - 1103

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

Synthesis of heteroarylazulenes: transition metal free coupling strategy of azulene with heterocycles

Abstract

Keywords

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