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CORDIS

Sulfur Enabled Annulations for Modular, Efficient and General Routes into Oxazoles

Project description

A more efficient method to produce nitrogen-based compounds

Nitrogen-containing ring structures (heterocycles) are widely used in the pharmaceutical and agrochemical industries. New methods to prepare them more efficiently and with greater flexibility are needed. Recently, ‘nucleophilic nitrenoids’ have rapidly emerged as highly effective reactants for the assembly of different nitrogen-containing heterocycles. The reactivity and selectivity of this method depends on the combination of gold catalysis and highly reactive species called donor-activated alkynes. Funded by the Marie Skłodowska-Curie Actions programme, the SEAROX project will develop a more general method for preparing nitrogen-based heterocycles. By demonstrating the ability of sulfur-based directing groups to impart unprecedented regioselectivity to intermolecular reactions, the project will take the nitrenoid method beyond the limitations of donor-activated alkynes and will significantly impact the gold catalysis field.

Objective

SEAROX will bring together the complementary expertise of Dr Prakash Sekar (ER, expertise in cross-coupling and directing effects in metal catalysis) with Dr Paul Davies (Host, expertise in gold catalysis, sulfur-based reaction development and nucleophilic nitrenoids) to pioneer the use of sulfur-based directing groups to establish optimal gold-catalysed annulations. SEAROX will deliver an efficient, modular and readily diversifiable method to access important motifs with broad utility in academic and industrial R+D. By reducing the chemical and energy demand of complex molecule preparation, the European science base and economy benefits from enhanced sustainability. Nucleophilic nitrenoids have emerged as highly effective reactants for the preparation of the nitrogen-based heterocycles ubiquitous across biologically active species and vital to the pharmaceutical and agrochemical industries. The novel reactivity and high selectivity from such methods depend on using strongly donor-activated alkynes. However, as the donor group translates into the products it limits their application. SEAROX will access more general and practically accessible heterocycle preparations by addressing the problems of donor-substitution. This project will also influence the wider gold catalysis field by establishing how S-directing effects impart unprecedented regioselectivity in intermolecular reactions. New substitution patterns and functional group combinations are needed to better probe chemical space in early stage drug discovery and SEAROX will equip PS with the skills to integrate scaffold and library design aspects within the new methods to deliver focused libraries of structurally-diverse oxazoles for phenotypic screening.

Coordinator

THE UNIVERSITY OF BIRMINGHAM
Net EU contribution
€ 212 933,76
Address
Edgbaston
B15 2TT Birmingham
United Kingdom

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Region
West Midlands (England) West Midlands Birmingham
Activity type
Higher or Secondary Education Establishments
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Total cost
€ 212 933,76