N-Alkylation of Some Imidazopyridines

Year 2025, Volume: 50 Issue: 1, 15 - 20, 25.03.2025

Fatıma Doğanç , Ali Hakan Göker

https://doi.org/10.55262/fabadeczacilik.1577453

Abstract

6-Bromo-2-(4-(4-fluorophenoxy)phenyl)-4H-imidazo[4,5-b]pyridine (I) and 2-[4-(4-fluorophenoxy)phenyl]-5H-imidazo[4,5-c]pyridine (III) were prepared by the reaction of 5-bromo-2,3-diaminopyridine and 3,4-diaminopyridine with sodyum metabisulfite adduct of 4-(4-fluorophenoxy)benzaldehyde (1), respectively. Alkylation of these compounds with 1-(chloromethyl)-4-methoxybenzene under basic conditions (K2CO3) in DMF) were formed as mainly N4 regioisomer (II) and N5 regioisomer (IV). Their regioisomeric structures were assigned with 2D-NOESY (Nuclear Overhauser Effect Spectroscopy) spectra.

Keywords

imidazopyridines, NOESY, regioisomers

Thanks

Central Laboratory of Pharmacy, Faculty of Ankara University provided support for acquisition of NMR and mass spectrometer used in this work.

Bazı İmidazopiridinlerin N-Alkilasyonu

Abstract

5-Bromo-2,3-diaminopiridin ve 3,4-diaminopiridinin, 4-(4-florofenoksi)benzaldehitin (1) sodyum metabisülfit tuzuyla ile reaksiyona sokulmasıyla sırasıyla 6-bromo-2-(4-(4-florofenoksi)fenil)-4H-imidazo[4,5-b]piridin (I) ve 2-[4-(4-florofenoksi)fenil]-5H-imidazo[4,5-c]piridin (III) bileşikleri elde edildi. Bu bileşiklerin 1-(klorometil)-4-metoksibenzen ile bazik koşullar altında (DMF içinde K2CO3) alkilasyonuyla esas olarak N4 regioizomeri (II) ve N5 regioizomeri (IV) olarak oluştu. Regioizomerik yapıları 2D-NOESY (Nükleer Overhauser Etki Spektroskopisi) spektrumları ile belirlendi.

Keywords

imidazopiridin, NOESY, regioizomer

References

• Doganc, F., Aydin, A. S., Şahin, E., Göker, H. (2020). Regioselective N-alkylation of some 2 or 6-chlorinated purine analogues. Journal of Molecular Structure, 1272, 134200. doi : 10.1016/j.molstruc. 2022.134200