Russian Journal of Organic Chemistry

, Volume 54, Issue 10, pp 1519–1530 | Cite as

Synthesis of Epimethanetriyloxazoloand Epimethanetriylimidazobenzazocinones and -benzazoninones from syn- and anti-Atropisomers of N-Acyl-N-[2-(cycloalk-2-en-1-yl)-6-methylphenyl]glycines

  • L. A. Aleksandrova
  • A. A. Fatykhov
  • A. R. Gataullina
  • E. A. Kantor
  • R. R. GataullinEmail author


The major product of intramolecular [3 + 2]-cycloaddition of münchnones generated by heating syn- and anti-atropisomers of N-acetyl-N-[2-(cyclopent-2-en-1-yl)-6-methyl-, 2,4-dimethyl-, 2,5-dimethylphenyl)- and N-acetyl-N-[2-(cyclohex-2-en-1-yl)-6-methylphenyl]glycines with acetic anhydride was that formed from the anti isomer. Isomeric glycine derivatives having no methyl group in the ortho position of the aromatic ring gave rise to (1S*,3aR*,4S*,7S*,13S*)-1-methyl- and (1S*,3aR*,4S*,7S*,13S*)-3a-acetyl-1-methyl-4,5,6,7- tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin-3(3aH)-one as the major product. Treatment of 1,11-dimethyl- and 1,9,11-trimethyl-4,5,6,7-tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin- 3(3aH)-ones with methylamine in methanol on heating in a sealed ampule afforded epimethanetriylimidazobenzazocinones, whereas acid-stable compound with a methanocyclopenta[c]quinoline skeleton was formed under similar conditions from the 1,8,11-trimethyl analog.


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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • L. A. Aleksandrova
    • 1
  • A. A. Fatykhov
    • 1
  • A. R. Gataullina
    • 2
  • E. A. Kantor
    • 2
  • R. R. Gataullin
    • 1
    Email author
  1. 1.Ufa Institute of ChemistryRussian Academy of SciencesUfa, BashkortostanRussia
  2. 2.Ufa State Petroleum Technological UniversityUfa, BashkortostanRussia

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