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

7 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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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