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Journals / Fabad Eczacılık Bilimler Dergisi / 2026 / Cilt: 50 Sayı: 1

N-Alkylation of Some Imidazopyridines

Bazı İmidazopiridinlerin N-Alkilasyonu

Fatıma Doğanç(ANKARA ÜNİVERSİTESİ, ECZACILIK FAKÜLTESİ, ECZACILIK PR.)0000-0002-1832-587X
Ali Hakan Göker(ANKARA ÜNİVERSİTESİ, ECZACILIK FAKÜLTESİ)0000-0002-9366-6949
Pages
15–20
Publication Date
2025-03-25
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Their regioisomeric structures were assigned with 2D-NOESY (Nuclear Overhauser Effect Spectroscopy) spectra.

📌 3 Key Takeaways

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Objective & Hypothesis: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.
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Key Findings & Data: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).
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Conclusion & Impact:Their regioisomeric structures were assigned with 2D-NOESY (Nuclear Overhauser Effect Spectroscopy) spectra.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:imidazopiridin · NOESY · regioizomer

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.

Özet

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.

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Cite This Article

Doğanç, F., Göker, A. H. (2025). N-Alkylation of Some Imidazopyridines. Fabad Eczacılık Bilimler Dergisi, Cilt: 50 Sayı: 1, 15–20. https://doi.org/10.55262/fabadeczacilik.1577453

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References (2)

  1. 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
  2. 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