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Synthesis 1987; 1987(11): 990-992
DOI: 10.1055/s-1987-28144
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Synthesis of 4-Unsubstituted ß-Lactams via Dithiocarbonimidates

S. D. Sharma* , Usha Mehra, J. P. S. Khurana, S. B. Pandhi
  • *Department of Chemistry, Panjab University, Chandigarh 160014, India
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Publikationsdatum:
12. September 2002 (online)

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Cycloaddition of dithiocarbonimidate 1 to the ketene generated in situ from phenoxyacetylchloride in the presence of triethylamine affords the 4-dithioalkyl-2-azetidinones 2 in good yields. Facile conversion of 2 to the 4-unsubstituted ß-lactams 3 can be accomplished by desulfurization with Raney-Nickel. Formation of several interesting products during attempts to bring a carbonyl function at C-4 in 2 has also been described.