Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones

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

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

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[5.3.1.04,9]undecan-2,6-dione 9a, 1-isopropenyl-4(N-morpholino)tricyclo[5.3.1.04,9]undecan-2,6-dione 9b, and 1-methyl-4(N-morpholino)tricyclo[5.3.1.04,9]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[5.3.1.04,9]undecan-2,6-dione 9d and 8(R)-methyl-1-phenyl-4(N-pyrrolidinyl)tricyclo[5.3.1.04,9] 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
JournalTetrahedron
Volume57
Issue number15
DOIs
Publication statusPublished - 2001 Apr 9
Externally publishedYes

Keywords

  • 4,4-disubstituted cyclohexanone
  • Acryloyl chloride
  • Enamine
  • Morpholine
  • Pyrrolidine
  • Substituted adamantane-2,4-dione
  • Substituted tricyclo [5.3.1.0]undecan-2,6-dione

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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  • Cite this

    Giasuddin Ahmed, M., Iqbal Moeiz, S. M., Asghari Ahmed, S., Kiuchi, F., & Tsuda, Y. (2001). Synthesis of substituted tricyclo[5.3.1.04,9]undecan-2,6-diones. Tetrahedron, 57(15), 3143-3150. https://doi.org/10.1016/S0040-4020(01)00172-7