(4 + 2) Annulation of ClNHCHSiMeCHCl and Propynones for the Synthesis of 1,3-Azasilinones.

Org Lett

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

Published: September 2022

A useful 1,3-, reagent (ClNHCHSiMeCHCl) and its (4 + 2) annulation with propynones have been developed. The (4 + 2) annulation is promoted by NaHCO an intermolecular -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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http://dx.doi.org/10.1021/acs.orglett.2c02665DOI Listing

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