Copper(I)-Catalyzed One-Pot Sequential [3+2]/[8+2] Annulations for the ( Z)-Selective Construction of Heterocyclic Diazabicyclo[5.3.0]decatrienes.

An efficient copper(I)-catalyzed one-pot domino reaction for the ( Z)-selective construction of diazabicyclo[5.3.0]decatriene derivatives under mild conditions has been developed. This protocol was initiated by a Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC), followed by a ring opening rearrangement and then subsequent higher-order [8+2] cycloaddition of azaheptafulvene with ketenimine intermediates at the corresponding C-2 and N-3 sites, affording biologically active heterocycles in good to high yields. [ABSTRACT FROM AUTHOR]