Abstract
A convenient synthetic protocol for structurally novel and strained highly derivatized tricyclic β-lactams has been developed. The synthesis involves CeCl 3·7H 2O/NaI catalyzed addition–condensation of mercaptoacetic acid and N-aroyl- N′-arylidenehydrazines followed by intramolecular cyclodehydration to afford bicyclic 5 H-thiazolo[4,3- b][1,3,4]-oxadiazoles, which on treatment with acid chlorides in the presence of triethylamine furnish highly derivatized tricyclic 3 H-azetidino[2,1- b]-thiazolo[3,4- d][1,3,4]-oxadiazol-6-ones in 80–93% yields. The process presents an excellent illustration of Ce(III)-catalyzed C–C, C–N and C–S bond formation in a one-pot procedure.
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