Push–pull fluorenones and benzazulenequinones

regioselective [4+2] and [2+2] cycloadditions of benzopentalenequinone derivative and alkynes bearing an aniline moiety

Shin ichiro Kato, Tomokazu Kijima, Yoshihito Shiota, Toshitada Yoshihara, Seiji Tobita, Kazunari Yoshizawa, Yosuke Nakamura

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The reaction of benzopentalenequinone with alkynes bearing an aniline moiety provides access to two classes of push–pull chromophores with interesting optoelectronic properties. The regioselective [4+2] cycloaddition/[4+1] retrocycloaddition sequence gives fluorenone derivatives, and the formal regioselective [2+2] cycloaddition/ring-opening reaction in polar solvents generates hitherto unknown benzazulenequinone derivatives.

Original languageEnglish
Pages (from-to)4604-4607
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number41
DOIs
Publication statusPublished - Jan 1 2016

Fingerprint

Bearings (structural)
Alkynes
Cycloaddition
Cycloaddition Reaction
Derivatives
Chromophores
Optoelectronic devices
aniline

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Push–pull fluorenones and benzazulenequinones : regioselective [4+2] and [2+2] cycloadditions of benzopentalenequinone derivative and alkynes bearing an aniline moiety. / Kato, Shin ichiro; Kijima, Tomokazu; Shiota, Yoshihito; Yoshihara, Toshitada; Tobita, Seiji; Yoshizawa, Kazunari; Nakamura, Yosuke.

In: Tetrahedron Letters, Vol. 57, No. 41, 01.01.2016, p. 4604-4607.

Research output: Contribution to journalArticle

@article{2f36b401fc2e4bf6a11e488cb422b5fd,
title = "Push–pull fluorenones and benzazulenequinones: regioselective [4+2] and [2+2] cycloadditions of benzopentalenequinone derivative and alkynes bearing an aniline moiety",
abstract = "The reaction of benzopentalenequinone with alkynes bearing an aniline moiety provides access to two classes of push–pull chromophores with interesting optoelectronic properties. The regioselective [4+2] cycloaddition/[4+1] retrocycloaddition sequence gives fluorenone derivatives, and the formal regioselective [2+2] cycloaddition/ring-opening reaction in polar solvents generates hitherto unknown benzazulenequinone derivatives.",
author = "Kato, {Shin ichiro} and Tomokazu Kijima and Yoshihito Shiota and Toshitada Yoshihara and Seiji Tobita and Kazunari Yoshizawa and Yosuke Nakamura",
year = "2016",
month = "1",
day = "1",
doi = "10.1016/j.tetlet.2016.09.002",
language = "English",
volume = "57",
pages = "4604--4607",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "41",

}

TY - JOUR

T1 - Push–pull fluorenones and benzazulenequinones

T2 - regioselective [4+2] and [2+2] cycloadditions of benzopentalenequinone derivative and alkynes bearing an aniline moiety

AU - Kato, Shin ichiro

AU - Kijima, Tomokazu

AU - Shiota, Yoshihito

AU - Yoshihara, Toshitada

AU - Tobita, Seiji

AU - Yoshizawa, Kazunari

AU - Nakamura, Yosuke

PY - 2016/1/1

Y1 - 2016/1/1

N2 - The reaction of benzopentalenequinone with alkynes bearing an aniline moiety provides access to two classes of push–pull chromophores with interesting optoelectronic properties. The regioselective [4+2] cycloaddition/[4+1] retrocycloaddition sequence gives fluorenone derivatives, and the formal regioselective [2+2] cycloaddition/ring-opening reaction in polar solvents generates hitherto unknown benzazulenequinone derivatives.

AB - The reaction of benzopentalenequinone with alkynes bearing an aniline moiety provides access to two classes of push–pull chromophores with interesting optoelectronic properties. The regioselective [4+2] cycloaddition/[4+1] retrocycloaddition sequence gives fluorenone derivatives, and the formal regioselective [2+2] cycloaddition/ring-opening reaction in polar solvents generates hitherto unknown benzazulenequinone derivatives.

UR - http://www.scopus.com/inward/record.url?scp=84987981760&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84987981760&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2016.09.002

DO - 10.1016/j.tetlet.2016.09.002

M3 - Article

VL - 57

SP - 4604

EP - 4607

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 41

ER -