Direct methods for the preparation of heterocycles and bis-heteroaromatics
Lead Research Organisation:
CARDIFF UNIVERSITY
Department Name: Chemistry
Abstract
Within this project we will develop new reagent based methodology to provide simple, robust and highly practical synthetic methods of broad applicability within organic synthesis. N-Methyl-O-tosyl hydroxylamine will provide a new method for the direct conversion of both aldehydes and ketones to alpha-oxysulfonyl carbonyl compounds, which, when treated directly with a variety of bis-hetero nucleophiles in-situ will provide a one-pot reaction sequence to access a variety of biologically significant heterocycles. Buchwald coupling of N-methyl-O-benzoyl hydroxylamine (and analogues) with aryl halides will lead to a cascade reaction sequence to provide direct access to bis-functionalised heteroaromatics which are present in a wide variety of both synthetic and naturally occurring compounds of biological importance. Application of these new methods to the praparation of targeted chemical arrays will provide access to a series of densely functionalised products for biological assay.
People |
ORCID iD |
Nicholas Tomkinson (Principal Investigator) |
Publications
Jones KL
(2008)
Copper-catalyzed coupling of hydroxylamines with aryl iodides.
in Organic letters
Porzelle A
(2009)
Palladium-catalyzed coupling of hydroxylamines with aryl bromides, chlorides, and iodides.
in Organic letters
Porzelle A
(2010)
Rearrangement strategy for the synthesis of 2-aminoanilines.
in Organic letters
Porzelle A
(2008)
Rearrangement of Differentially Protected N -Arylhydroxylamines
in European Journal of Organic Chemistry
Porzelle A
(2010)
Synthesis of benzoxazolones from nitroarenes or aryl halides.
in Organic letters
Description | GlaxoSmithKline R & D Ltd |
Organisation | GlaxoSmithKline (GSK) |
Country | Global |
Sector | Private |
Start Year | 2007 |