Journal of Heterocyclic Chemistry · 2018 · 14 citations · 14 references
Natural SciencesChemistryMedicinal ChemistryCatalysisGreen ChemistryOrganic ChemistryHeterocycle SynthesisOrganic SynthesisSafer Chemical SynthesisSolvent-free SynthesisAzetidine ChemistryCatalyst DevelopmentCycloaddition ReactionsElectrophilic ReactivityNucleophilic ReactivitySchiff Base CatalysisTriazole ChemistryTriazole Synthesis
We have synthesized the novel 2‐azetidinone derivatives by using Schiff bases of 1,2,4‐triazoles via a single step protocol. We used DABCO as a good homogenous, ecofriendly, highly reactive, easy to handle, and nontoxic catalyst. In DABCO catalyzed synthesis of active 2‐oxo‐azetidine, a highly electrophilic ketene intermediate can react with weakly nucleophilic (N═CH) linkage, which is used as the precursor for the cycloaddition reaction to deliver the desired products in excellent yields with protic solvents. In addition, the DABCO as an economically viable and readily available catalyst is soluble in almost all solvents and their salts easily filtered off from the reaction medium. Moreover, this new synthetic protocol features high conversion in green solvents and a straightforward procedure.
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Maria Gabriella Vigorita, Rosaria Ottanà, Francesca Monforte et al. · Bioorganic & Medicinal Chemistry Letters · 2001 · 141 citations