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.
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