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
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- 作者：Boris A. Trofimov ; Elena Yu. Schmidt ; Al’ ; bina I. Mikhaleva ; Igor A. Ushakov ; Nadezhda I. Protsuk ; Elena Yu. Senotrusova ; Olga N. Kazheva ; Grigorii G. Aleks ; rov ; Oleg A. Dyachenko
- 关键词：4-Methylene-3-oxa-1-azabicyclo[3.1.0]hexanes ; Alkyl aryl ketoximes ; Acetylene ; Acetone ; Superbases ; Aziridines
- 刊名：Tetrahedron Letters
- 出版年：2009
- 出版时间：1 July 2009
- 年：2009
- 卷：50
- 期：26
- 页码：3314-3317
- 全文大小：991 K
文摘
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.