Synthesis and emission properties of 1,6-methano[10]annulene-3,4- dicarboximides

Shigeyasu Kuroda*, Naoko Tamura, Ryuta Miyatake, Naoko Matsumoto, Yoshikazu Horino, Daisuke Miyawaki, Mitsunori Oda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A mixture of 1,6-methano[10]annulene-3,4-dicarboximide (1e) and 1,6-methano[10]annulene-3,4-dicarboxylic anhydride (3) was obtained through a two-step sequence involving cyanation and subsequent hydrolysis from ethyl 4-bromo-1,6-methano[10]annulene-3-carboxylate (5). Alkylations of 1e provided 1f and 1g, and the nucleophilic substitution of p-fluoronitrobenzene with 1e yielded 1i. Copper-catalyzed arylations of 1e with arylhalides gave 1a and 1h. Reactions of 3 with anilines afforded 1a and 1h. Emission properties of the imides obtained are also reported.

Original languageEnglish
Pages (from-to)789-796
Number of pages8
JournalHeterocycles
Volume83
Issue number4
DOIs
StatePublished - 2011/03/28

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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