Syntheses and acid-stimulus responsiveness of aminobenzopyranoxanthene spiroethers

Ryosuke Hosoda, Shinichiro Kamino, Masashi Ueda, Daisuke Sawada

Research output: Contribution to journalArticle

Abstract

Novel aminobenzopyranoxanthene spiroethers (ABPX-SEs) based on the spirocyclization of the hydroxymethyl group were synthesized from ABPX spirolactones (ABPX-SLs). The addition of an acid induces a ring-opening reaction to yield two colored monocationic and dicationic spiro-ring species of ABPX. The acid-stimulus responsiveness of the ABPX-SEs is lower than that of ABPX-SLs in polar organic solvents. In addition, the ABPX-SEs exhibit stepwise structural changes of the three equilibrium species at acidic pH, although rapid conversion from the spirolactone to dicationic species occurs in the case of ABPX-SLs.

Original languageEnglish
Pages (from-to)820-824
Number of pages5
JournalHeterocycles
Volume99
Issue number2
DOIs
Publication statusPublished - 2019

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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