10-Hydroxy-7-arylindeno[1,2-b]-1,2,5-oxadiazolo[3,4-d]pyridines and 7- aryl-10-oxoindeno[1,2-b]-1,2,5-oxadiazolo[3,4-d]pyridines-synthesis, spectra, and polymorphism

Shuntaro Mataka, Hideki Gorohmaru, Thies Thiemann, Tsuyoshi Sawada, Kazufumi Takahashi, Akiyoshi Tori-i

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


The novel dyes 7-aryl- 10-oxoindeno[1,2-b]-1,2,5-oxadiazolo[3,4-d]- pyridines (4) and 7-aryl-10-hydroxyindeno[1,2-b]-1,2,5-oxadiazolo[3,4-d]- pyridines (5) have been prepared from acetophenone derivatives. While compounds (4) exhibit a dark red color, they are only weakly fluorescent. Compounds (5) is fluorescent. Of interest is that 10-hydroxy-7-phenylindeno- [1,2-b]-1,2,5-oxadiazolo[3,4-d] pyridine (5a) can take four polymorphic forms in the solid state, of which two are yellow (designated as 5a-Y-1 and 5a-Y-2) and two are red (5a-R-1 and 5a-R-2). Two of them are interconvertible (yellow/red) upon exposure to different solvents. X-Ray crystal structure analysis of 5a-R-2 shows the phenyl ring and the indenooxadiazolopyridine ring to be coplanar.

Original languageEnglish
Pages (from-to)895-902
Number of pages8
Issue number2
Publication statusPublished - Apr 1 1999
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry


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