Russian Journal of Organic Chemistry

, Volume 43, Issue 7, pp 1065–1079 | Cite as

New type of transannular reactions in azirine-fused medium-size heterocycles: Selective transformations of azirino[2,1-e][1,6]benzoxazocines and -benzothiazocines into oxa(thia)zine and oxa(thia)zole derivatives

  • E. Yu. Shinkevich
  • M. S. Novikov
  • A. F. Khlebnikov
  • R. R. Kostikov
  • J. Kopf
  • J. Magull


Opening of the three-membered ring in heterocyclic systems incorporating a dichloroaziridine ring fused to eight-membered O,N-or S,N-heterocycles is accompanied by transannular reactions with participation of the endocyclic oxygen and sulfur atoms. Depending on the conditions, the products are 1,4-benzoxazine (1,4-benzothiazine) or 1,3-benzoxazole (1,3-benzothiazole) derivatives. The discovered transformations were used as a basis of methods for the preparation of new heterocyclic systems, 2,3,4,4a-tetrahydro-1H-pyrido-[3,2-b][1,4]benzoxa(thia)zine derivatives, in domino or consecutive modes, as well as of pyrrolidinyl-substituted 1,3-benzoxa(thia)zoles.


Benzoxazine Benzoxazole Benzothiazine Powdered Potassium Hydroxide Transannular Cyclization 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • E. Yu. Shinkevich
    • 1
  • M. S. Novikov
    • 1
  • A. F. Khlebnikov
    • 1
  • R. R. Kostikov
    • 1
  • J. Kopf
    • 2
  • J. Magull
    • 3
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia
  2. 2.Institute of Inorganic ChemistryHamburgGermany
  3. 3.Institute of Inorganic ChemistryGeorg-August UniversityGöttingenGermany

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