Title of article
One-pot assembly of 4-methylene-3-oxa-1-azabicyclo[3.1.0]hexanes from alkyl aryl(hetaryl) ketoximes, acetylene, and aliphatic ketones: a new three-component reaction
Author/Authors
Trofimov، نويسنده , , Boris A. and Schmidt، نويسنده , , Elena Yu. and Mikhaleva، نويسنده , , Alʹbina I. and Ushakov، نويسنده , , Igor A. and Protsuk، نويسنده , , Nadezhda I. and Senotrusova، نويسنده , , Elena Yu. and Kazheva، نويسنده , , Olga N. and Aleksandrov، نويسنده , , Grigorii G. and Dyachenko، نويسنده , , Oleg A.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2009
Pages
4
From page
3314
To page
3317
Abstract
A new three-component reaction between alkyl aryl(hetaryl)ketoximes, acetylene, and aliphatic ketones in the superbasic systems KOH/DMSO and LiOH/CsF/DMSO (70–90 °C, initial acetylene pressure 13–15 atm, 5–60 min) affords novel 4-methylene-3-oxa-1-azabicyclo[3.1.0]hexanes in yields of up to 75%. Using KOH/DMSO, the side products of the reaction are O-vinylketoximes and 2-aryl(hetaryl)pyrroles, while with LiOH/CsF/DMSO, the reaction proves to be selective, only minor amounts of the corresponding alkyl aryl(hetaryl) ketones being detectable.
Keywords
Alkyl aryl ketoximes , Superbases , Acetone , Aziridines , Acetylene
Journal title
Tetrahedron Letters
Serial Year
2009
Journal title
Tetrahedron Letters
Record number
1864318
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