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Communication | Regular issue | Vol 20, No. 2, 1983, pp.205-211
Published online, 1st January, 1970
DOI: 10.3987/R-1983-02-0205
1-(3-Diazo-2-oxopropyl)-4-thio-substituted Azetidine-2-ones. Versatile Intermediates for the Preparation of Bicyclic β-Lactams: Synthesis of Novel Cephem Derivatives

Hans Fliri, Ching-Pong Mak, Kapa Prasad, Gerhard Schulz, and Peter Stütz

*Sandoz Forschungsinstitut, 1235 Wien, Brunnerstraße 59, Austria


Metal-catalyzed thermal decomposition of diazoketones 3c-3f afforded different substituted cephems, whose formation can be rationalized by assuming different reaction pathways. Possible mechanisms are proposed, and the effect of various 4-thio-substituents on the decomposition of these diazoketones are summarised.