Browsing by Author "Sanchez-Velasco, Oriel A."

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    Synthesis of N-Arylcytisine Derivatives Using the Copper-Catalyzed Chan-Lam Coupling
    (2021) Sanchez-Velasco, Oriel A.; Saavedra-Olavarria, Jorge; Araya-Santelices, Daniel A. A.; Hermosilla-Ibanez, Patricio; Cassels, Bruce K.; Perez, Edwin G.
    N-Arylcytisine derivatives are quite rare. We report here a practical methodology to obtain these compounds. Using the copper-catalyzed Chan-Lam coupling, we synthesized new N-arylcytisine derivatives at room temperature, in air and using inexpensive phenylboronic acids. Cytisine and 3,5-dihalocytisines can act as substrates, and among the products, the p-Br-derivative 2r was used as a substrate to obtain biaryl derivatives under Pd-coupling conditions; ester 2j was converted into its acid and amide derivatives using classical carbodiimide conditions. This shows that the Chan-Lam cross-coupling reaction can be included as a versatile synthetic tool in the derivatization of natural products.