SEAROX · Sulfur Enabled Annulations for Modular, Efficient and General Routes into Oxazoles
Horizon 2020 — Marie Skłodowska-Curie Actions
- Duration
- 2019-08-07 → 2021-08-06
- EU contribution
- €212,934
- Participants
- 1
- Scheme
- MSCA-IF-EF-ST
Lines connect the coordinator with its partners.
Results in brief
Sulfur Enabled Annulations for Modular, Efficient and General Routes into Oxazoles
Heterocycles, such as oxazoles, are critically important constituent motifs in several areas including bioactive compounds (e.g. drug discovery) and materials. However their preparation, especially with varied groups surrounding them, is very challenging and resource intensive. Methods that can be applied to different types of system are limited. Nucleophilic nitrenoids have emerged as highly effective reactants for the preparation of the nitrogen-based heterocycles that are ubiquitous across biologically active species and vital to the pharmaceutical and agrochemical industries. The nucleophilic nitrenoid approach however has been dependent on strongly donor-activated alkynes. As the donor group translates into the products it limits the application of these methods. Being able to combine the nucleophilic nitrenoid approach with more varied or useful alkynes would significantly increase the applicability of the methods, and hence enable faster, more flexible and more effective routes into important heterocyclic structures. SEAROX aimed to build upon a recent discovery in the host group and pioneer the use of sulfur-based directing groups to establish optimal gold-catalyzed annulations and address the problems of donor substitution. The research aim of SEAROX was to generate a truly general, rapid, modular entry into densely functionalised oxazoles. SEAROX will deliver an efficient 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.
Data: CORDIS, © European Union
Project 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.
Original text from CORDIS.
Participants
- THE UNIVERSITY OF BIRMINGHAM · BirminghamCoordinatorUnited Kingdom
Links
Data: CORDIS, © European Union