An Acid-Catalyzed Cascade Synthesis of Oxaazatetracyclo [5.5.0.03,11.05,9]dodecane Derivatives

Artyom E. Paromov, Sergey V. Sysolyatin, Yuri V. Gatilov

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A condensation between mesylamide and glyoxal under highly acidic conditions was studied. A series of new compounds whose structures contain a moiety of oxaazatetracyclo[5.5.0.03,11.05,9]dodecane were synthesized. The synthesis processes were optimized and main factors affecting the assembling of cage products were revealed. Assumptions are made regarding the formation mechanism of these chemical entities. For the first time, compounds have been obtained that include moieties of 2,6,8-trioxa-4,10,12-triazatetracyclo[5.5.0.03,11.05,9]dodecane and 2,4,6-trioxa-8,10,12-triazatetracyclo[5.5.0.03,11.05,9]dodecane. An X-ray diffraction analysis of the new compounds was performed.

Original languageEnglish
Pages (from-to)363-373
Number of pages11
JournalJournal of Energetic Materials
Volume35
Issue number3
DOIs
Publication statusPublished - 3 Jul 2017

Keywords

  • Cage compounds
  • cyclization
  • domino reactions
  • nitrogen heterocycles
  • oxygen heterocycles

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