Nitrogen-centered aziridinyl radicals and their synthetic applications.
Published: 2007
Language: eng
Number of pages: 41
ISBN-13: 9780494272763
Description: Nitrogen-centered aziridinyl radicals exhibit different properties from other types of nitrogen-centered radicals and have great potential for the construction of nitrogen-containing heterocycles. The studies of nitrogen-centered aziridinyl radicals in the literature have been limited to basic physical and chemical properties, and their synthetic utility remains undeveloped. We have found that nitrogen-centered azindinyl radicals can be generated through homolysis of N-haloaziridines which can be easily produced upon treatment of N-bromosuccinimide or N-iodosuccinimide with aziridinys. This methodology has been applied to the synthesis of a variety of beta-haloaziridines in moderate to good yields. Further transformation into piperazine derivatives was achieved via nucleophilic substitution at the beta position and oxalyl chloride coupling reaction. The resulting structure is present in a potential selective brain serotonin (5HT2A) antagonist.
Notes: Source: Masters Abstracts International, Volume: 45-06, page: 3162.

Thesis (M.Sc.)--University of Toronto, 2007.

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