Synthesis of substituted tricyclo[,9]undecan-2,6-diones

M. Giasuddin Ahmed, Syed M. Iqbal Moeiz, S. Asghari Ahmed, Fumiyuki Kiuchi, Yoshisuke Tsuda

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


The morpholine enamines of 4-acetyl-4-phenylcyclohexanone 3a, 4-acetyl-4-isopropenylcyclohexanone 3b, 4-acetyl-4-methylcyclohexanone 3c react with acryloyl chloride to give 1-phenyl-4(N-morpholino)tricyclo[,9]undecan-2,6-dione 9a, 1-isopropenyl-4(N-morpholino)tricyclo[,9]undecan-2,6-dione 9b, and 1-methyl-4(N-morpholino)tricyclo[,9]undecan-2,6-dione 9c, respectively, along with the corresponding substituted adamantane-2,4-diones. The morpholine enamine of 4-acetyl-4-benzylcyclohexa-none 3d and pyrrolidine enamine of 4-acetyl-4-phenylcyclohexanone 3a yield the corresponding 1-benzyl-4(N-morpholino)tricyclo[,9]undecan-2,6-dione 9d and 8(R)-methyl-1-phenyl-4(N-pyrrolidinyl)tricyclo[,9] undecan-2,6-dione 9e. No substituted adamantane-2,4-diones were formed in any of the latter two reactions.

Original languageEnglish
Pages (from-to)3143-3150
Number of pages8
Issue number15
Publication statusPublished - 2001 Apr 9
Externally publishedYes


  • 4,4-disubstituted cyclohexanone
  • Acryloyl chloride
  • Enamine
  • Morpholine
  • Pyrrolidine
  • Substituted adamantane-2,4-dione
  • Substituted tricyclo []undecan-2,6-dione

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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