Three-Component Synthesis of 7-Hydroxy-7-polyfluoroalkylhexahydroimidazo[1,2-a]­pyridin-5(1H)-ones

A new straightforward three‐component approach to 7‐hydroxy‐7‐(polyfluoroalkyl)hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones with high diastereoselectivity and regiospecificity was developed starting from commercially available 3‐oxo esters, methyl ketones, and 1,2‐ethanediamines. The scope of this cycl...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-10, Vol.2015 (28), p.6306-6314
Main Authors: Goryaeva, Marina V., Burgart, Yanina V., Kudyakova, Yulia S., Ezhikova, Marina A., Kodess, Mikhail I., Slepukhin, Pavel A., Saloutin, Victor I.
Format: Article
Language:English
Subjects:
Amines
Cyclization
Fluorine
Ketones
Multicomponent reactions
Nitrogen heterocycles
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Summary:A new straightforward three‐component approach to 7‐hydroxy‐7‐(polyfluoroalkyl)hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones with high diastereoselectivity and regiospecificity was developed starting from commercially available 3‐oxo esters, methyl ketones, and 1,2‐ethanediamines. The scope of this cyclization and its plausible mechanism are reported. The construction of polyfluoroalkylated hexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones was carried out in a one‐pot reaction starting from methyl ketones, 1,2‐ethanediamines, and fluorinated 3‐oxo esters.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500822