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

Autor:	Oleg A. Dyachenko, Al'bina I. Mikhaleva, Igor A. Ushakov, Nadezhda I. Protsuk, Olga N. Kazheva, Boris A. Trofimov, Elena Yu. Schmidt, Elena Yu. Senotrusova, G. G. Aleksandrov
Rok vydání:	2009
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Acetylene Component (thermodynamics) Aryl Organic Chemistry Drug Discovery Acetone Methylene Biochemistry Medicinal chemistry Alkyl
Zdroj:	Tetrahedron Letters. 50:3314-3317
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2009.02.085
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::328f307eaf7b19269653630085ba3846 https://doi.org/10.1016/j.tetlet.2009.02.085 Zobrazit plný text záznamu Full Text from ScienceDirect