Heterocyclization of gem-dichlorocyclopropanes: "Fine tuning" of reactivity towards nitronium triflate. Issue 30 (26th July 2017)

• Record Type: Journal Article
• Authors: Sedenkova, Kseniya N.; Averina, Elena B.; Grishin, Yuri K.; Kolodyazhnaya, Julia V.; Rybakov, Victor B.; Vasilenko, Dmitry A.; Steglenko, Dmitry V.; Minkin, Vladimir I.; Kuznetsova, Tamara S.; Zefirov, Nikolay S.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 30(2017)
• Page Start: 2955
• Page End: 2958
• Publication Date: 2017-07-26
• Subjects: Dichlorocyclopropanes -- Nitrogen heterocycles -- Multicomponent reactions -- Density functional calculations; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.06.047
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Dichlorocyclopropanes shows dual reactivity towards nitronium triflate. Addition of water leads to 4-chloropyrimidine N -oxides instead of isoxazoles. Pyrimidine N -oxide formation is promoted by the hydroxonium ion (DFT study). Abstract: The heterocyclization of gem -dichlorocyclopropanes upon treatment with nitronium triflate in organic nitriles was studied and the influence of the medium on the reaction pathway was shown. While in anhydrous solvent 5-chloroisoxazole was the only product, the admixture with water promoted a three-component heterocyclization affording 4-chloropyrimidine N -oxides. This phenomenon was rationalized using DFT calculations.