(4 + 2) Annulation of Cl-NH3+CH2SiMe2CH2Cl and Propynones for the Synthesis of 1,3-Azasilinones

Chang Ma; Yu Fan; Chunmei Zheng; Lu Gao; Wanshu Wang; Bowen Ke; Zhenlei Song

doi:10.1021/acs.orglett.2c02665

(4 + 2) Annulation of Cl^-NH₃⁺CH₂SiMe₂CH₂Cl and Propynones for the Synthesis of 1,3-Azasilinones

Org Lett. 2022 Sep 16;24(36):6631-6636. doi: 10.1021/acs.orglett.2c02665. Epub 2022 Sep 2.

Authors

Chang Ma¹, Yu Fan¹, Chunmei Zheng¹, Lu Gao¹, Wanshu Wang¹, Bowen Ke², Zhenlei Song¹

Affiliations

¹ 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.
² Department of Anesthesiology, Laboratory of Anesthesia and Critical Care Medicine, National-Local Joint Engineering Research Centre of Translational Medicine of Anesthesiology, West China Hospital, Sichuan University, Chengdu 610041, China.

PMID: 36054503
DOI: 10.1021/acs.orglett.2c02665

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes*
Alkylation
Nitrogen*

Substances

Alkenes
Nitrogen