Abstract

A useful 1,3-N,Si reagent (Cl-NH3+CH2SiMe2CH2Cl) and its (4 + 2) annulation with propynones have been developed. The (4 + 2) annulation is promoted by NaHCO3 via an intermolecular N-1,4-addition/intramolecular alkylation process, leading to 1,3-azasilinones in good yields. Diverse functionalization of the alkene, carbonyl, and nitrogen moieties on the 1,3-azasilinone has been demonstrated, showcasing the potential of the approach in the synthesis of bioactive molecules containing silaazacycles.

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