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1-Azetines, 1,2-Thiazetin-1,1-dioxides and Isothiazol-1,1-dioxides as Building Blocks in Heterocyclic Synthesis:\ud the Attempted Synthesis of Bicyclic β-Sultams

By Arnaud Pitard


This thesis is concerned with the synthesis of β-sultams and the development of new routes for the synthesis of bicyclic versions of these molecules as potential anti-bacterials. The synthesis of 1-azetines, 1,2-thiazetin-1,1-dioxides and isothiazol-1,1-dioxides as precursors of bicyclic heterocycles is described.\ud \ud \ud 1-Azetines were synthesised from azetidin-2-ones prepared via the [2+2] cycloaddition of alkenes with N-chlorosulfonyl isocyanate (CSI). They reacted with diphenylcyclopropenone or nitrile oxides to afford bicyclic systems whose reactivity was explored and afforded a range of heterocycles such as 1,2,4-oxadiazoles, pyridines or pyrimidines via novel reaction pathways.\ud \ud \ud The synthesis of 1,2-thiazetin-1,1-dioxide through two routes will be discussed: the alkylation of 3-oxo-β-sultams to afford 3-ethoxy-1,2-thiazetin-1,1-dioxides, and the ring contraction of an isothiazol-1,1-dioxide to afford a 3-diethylamino-1,2-thiazetin 1,1-dioxide. The reactivity of these 1,2-thiazetin-1,1-dioxides towards diphenylcyclopropenone, 1,3-dipoles and dienes was studied and is fully described.\ud \ud \ud In the course of chemistry mentioned above, a series of isothiazol-1,1-dioxides was synthesised. Their reaction with 1,3-dipoles to yield the corresponding bicyclic heterocycles is described

Topics: Q1, QD
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  2. (1983). Acta doi
  3. (1987). Circulation doi
  4. (2003). Drug Target-Infectious Disorders doi
  5. (1999). Hypotheses doi
  6. (1982). In Chemistry and Biology of β-Lactam Antibiotics; doi
  7. (1984). In Comprehensive Heterocyclic Chemistry I; Katritzk Eds.; Elsevier:
  8. (1984). In Comprehensive Heterocyclic Chemistry I; Katritzky, doi
  9. (1976). In Comprehensive Heterocyclic Chemistry II; doi
  10. (1990). In Comprehensive Medicinal Chemistry; Sammes,
  11. (1977). In Organic Chemistry of Sulfur; Oae, doi
  12. (1961). In Organic Sulfur Compounds; doi
  13. (1992). In Reactive Intermediates;
  14. (1992). In The Chemistry of β-Lactams; doi
  15. (2005). Molecules doi
  16. (1975). p g. Chem.
  17. (1990). Pays-Bas doi
  18. (2005). PhD Thesis,
  19. (1999). Phosphorus Sulfur Silicon Relat. doi
  20. (2005). sity of Huddersfield:
  21. (1962). Soc., Perkin Trans I
  22. (2007). Synlett doi
  23. (1981). Synthesis doi
  24. (2005). Thesis, doi
  25. (2007). tic Applications of 1,3-Dipolar Cycloaddition 2, p 361-472. 07. actions; 994,
  26. (2002). Trends in Heterocyclic Chemistry

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