Project description
Converting pyridines into other heterocycles
Pyridine, pyrrole, furan and thiophene are essential heteroaromatic compounds that are widely used to synthesise complex pharmaceuticals. The direct interconversion between heteroaromatic rings, essentially swapping atoms in the core structure, would greatly accelerate drug discovery by allowing late-stage modifications without the need for lengthy de novo synthesis. Supported by the Marie Skłodowska-Curie Actions programme, the PYR2HET project aims to develop a novel photochemical platform that transforms pyridines into pyrroles, furans and thiophenes. The method leverages pyridine N-oxidation and visible light to break apart pyridine rings into nitrile-containing diene chains. These versatile building blocks can then react with nitrenes, singlet oxygen or sulfur to form pyrrole, furan and thiophene rings, respectively.
Objective
Heteroaromatic like pyridines, pyrroles, furans, and thiophenes are privileged scaffolds in pharmaceuticals & agrochemicals. While functional group modifications are routine, direct interconversion between heteroaromatic rings typically requiring de novo synthesis . “Ring replacement” strategies could transform drug discovery by enabling late-stage modulations, yet no general methods exist for converting abundant pyridines into other heterocycles.
This project will pioneer a photochemical platform to directly convert pyridines into pyrroles, furans, and thiophenes. The approach exploits pyridine N-oxidation followed by visible-light-mediated deconstruction to nitrile-containing dienes. These intermediates will undergo divergent [4+1] cycloadditions with nitrenes, singlet oxygen, or sulfur to yield pyrroles, furans, and thiophenes, respectively.
The methodology will progress through: (1) development of pyridine-to-pyrrole transformation via Cu-catalysed nitrene insertion and rearrangement, (2) mechanistic elucidation, (3) extension to pyridine-to-furan and pyridine-to-thiophene conversions using singlet oxygen and elemental sulfur, and (4) demonstration of synthetic utility in late-stage ring replacement of drug molecules.
This disruptive strategy introduces the first general method for heteroaromatic-to-heteroaromatic replacement, a conceptually novel retrosynthetic paradigm. It transforms pyridines from static scaffolds into versatile precursors, enabling access to new heterocyclic space of high biological and industrial value.
Completion of this ambitious project at RWTH Aachen University will be supported by advanced mechanistic expertise, knowledge transfer, and dissemination, equipping the Researcher with unique skills at the interface of photochemistry, catalysis, and heteroaromatic synthesis and strongly enhancing her career trajectory toward independence.
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Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Project’s keywords as indicated by the project coordinator. Not to be confused with the EuroSciVoc taxonomy (Fields of science)
Programme(s)
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Multi-annual funding programmes that define the EU’s priorities for research and innovation.
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HORIZON.1.2 - Marie Skłodowska-Curie Actions (MSCA)
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Calls for proposals are divided into topics. A topic defines a specific subject or area for which applicants can submit proposals. The description of a topic comprises its specific scope and the expected impact of the funded project.
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Funding scheme (or “Type of Action”) inside a programme with common features. It specifies: the scope of what is funded; the reimbursement rate; specific evaluation criteria to qualify for funding; and the use of simplified forms of costs like lump sums.
HORIZON-TMA-MSCA-PF-EF - HORIZON TMA MSCA Postdoctoral Fellowships - European Fellowships
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(opens in new window) HORIZON-MSCA-2025-PF
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52062 Aachen
Germany
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