Azatriquinane, azatriquinacene, and a remarkable dimerization product

Mark Mascal, Nicholas M. Hext, Oleg V. Shishkin

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


Azatriquinane, an amine with a rigid, hemispherical topology, is synthesized in six steps from pyrrole. It is shown to be more basic than quinuclidine, and can be dimerized by N-oxidation and treatment with base to give novel, highly strained heptacycle. Oxidation with chlorine gives an azatriquinacene, a theoretical precursor to diazadodecahedrane.

Original languageEnglish (US)
Pages (from-to)131-134
Number of pages4
JournalTetrahedron Letters
Issue number1
StatePublished - Jan 1 1996
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery


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