LEWIS-PYR · Electrophilic aromatic substitution of azines catalysed by Frustrated Lewis pairs
Horizon 2020 — Marie Skłodowska-Curie Actions
- Duration
- 2021-05-01 → 2023-04-30
- EU contribution
- €172,932
- Participants
- 1
- Scheme
- MSCA-IF
Lines connect the coordinator with its partners.
Results in brief
Electrophilic aromatic substitution of azines catalysed by Frustrated Lewis pairs
Pyridine is the most common nitrogen-containing aromatic heterocycle employed as the core structure in a number of drugs in the pharmaceutical science. Since the discovery of first deuterated drug, these compounds are crucial for applicability in absorption, distribution, metabolism, and excretion (ADME) studies, and indicated vital roles in medicinal chemistry via boosting pharmacokinetic and pharmacodynamic properties of drug. Therefore, it is very much important to provide site-selective methodology for installation of hydrogen isotopes at various positions of pyridine and related heterocycles. Our research laboratory found that a range of pyridine containing heterocycles can be labeled with deuterium in site-selective manner. This discovery will open door for new types of deuterium labelled pharmaceutical drugs.
Data: CORDIS, © European Union
Project objective
Azines are nitrogen-containing aromatic rings of utmost synthetic relevance in natural products, pharmaceuticals, agrochemicals and materials science. Although nucleophilic aromatic substitution techniques are routine, these methods require air-sensitive and highly reactive nucleophiles, in most instances organometallic reagents. In sharp contrast, electrophilic aromatic substitutions are particularly difficult to the electron-poor nature of the azines, inevitably requiring harsh reaction conditions. Taking into consideration the wider availability of electrophilic partners when compared to their corresponding nucleophilic congerener, the development of a catalytic technique aimed at providing a mild, chemoselective and site-selective electrophilic aromatic substitution of azines will have tremendous consequences for the praxis of heterocyclic chemistry, particularly in late-stage applications. Aimed at providing a solution to such goal, LEWIS-PYR will design a conceptually new platform to activate unbiased azines via electrophilic aromatic substitution by using frustrated Lewis Pairs (FLPs) as a polarity inversion vehicles, allowing to substitute a series of a priori electron-poor nitrogen-containing electrocycles with a wide variety of different electrophilic partners.
Original text from CORDIS.
Participants
- FUNDACIO INSTITUT CATALA D'INVESTIGACIO QUIMICA · TARRAGONACoordinatorSpain
Links
Data: CORDIS, © European Union