SavedAdd your journal

Journals / Ankara Üniversitesi Eczacılık Fakültesi Dergisi / 2026 / Cilt: 49 Sayı: 1

REGIOISOMERIC N-ALKYLATION OF SOME INDAZOLES

Fatıma Doğanç(ANKARA ÜNİVERSİTESİ, ECZACILIK FAKÜLTESİ)0000-0002-1832-587X
Ali Hakan Göker(ANKARA ÜNİVERSİTESİ, ECZACILIK FAKÜLTESİ)0000-0002-9366-6949
Pages
103–108
Publication Date
2025-01-20
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

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

Their structures were established by combination of 1H-1H NOE (Nuclear Overhauser Effect Spectroscopy, NOESY) and HMBC (Heteronuclear Multiple Bond Correlation) NMR methods.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Objective: Indazole scaffold have two interconvertible tautomeric forms.
📊
Key Findings & Data:Based on our previous studies, regioisomeric N-alkylation of some indazole analogs was synthesized in this study and their structures were elucidated by 2D NMR methods.
💡
Conclusion & Impact:Their structures were established by combination of 1H-1H NOE (Nuclear Overhauser Effect Spectroscopy, NOESY) and HMBC (Heteronuclear Multiple Bond Correlation) NMR methods.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:HMBC · indazol (1 · 2-benzodiazol)

Abstract

Objective: Indazole scaffold have two interconvertible tautomeric forms. Based on our previous studies, regioisomeric N-alkylation of some indazole analogs was synthesized in this study and their structures were elucidated by 2D NMR methods. Material and Method: Regioisomers were resolved for N-benzylations and alkylation of some non-substituted and substituted indazoles, under basic conditions (K2CO3) in DMF. Result and Discussion: It was observed that, their occurrence ratios of N1 : N2 is almost equal (50%). Their structures were established by combination of 1H-1H NOE (Nuclear Overhauser Effect Spectroscopy, NOESY) and HMBC (Heteronuclear Multiple Bond Correlation) NMR methods.

Özet

Amaç: İndazol halkası iki tautomerik forma sahiptir. Önceki çalışmalarımızda yola çıkarak, bu çalışmada bazı indazol analoglarının regioizomerik N-alkilasyonu sentezlendi ve yapıları 2D NMR yöntemleriyle aydınlatıldı. Gereç ve Yöntem: Bazı non-sübstitüe ve sübstitüe indazollerin, DMF içinde bazik koşullar (K2CO3) altında N-alkilasyonu yoluyla regioizomerik N-alkilasyon türevleri elde edildi. Sonuç ve Tartışma: N1 : N2 oluşum oranlarının neredeyse eşit olduğu (%50) gözlemlendi. Moleküllerin yapıları, 1H-1H NOE (Nuclear Overhauser Effect Spectroscopy, NOESY) ve HMBC (Heteronuclear Multiple Bond Correlation) NMR yöntemleri ile aydınlatıldı.

🔖

Cite This Article

Doğanç, F., Göker, A. H. (2025). REGIOISOMERIC N-ALKYLATION OF SOME INDAZOLES. Ankara Üniversitesi Eczacılık Fakültesi Dergisi, Cilt: 49 Sayı: 1, 103–108. https://doi.org/10.33483/jfpau.1571272

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (11)

  1. Gaikwad, D.D., Chapolikar, A.D., Devkate, C.G., Warad, K.D., Tayade, A.P., Pawar, R.P., Domb, A.J. (2015) Synthesis of indazole motifs and their medicinal importance: An overview. European Journal of Medicinal Chemistry, 90, 707-731. [CrossRef]
  2. Alam, R.M., Keating, J.J. (2021). Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution. Beilstein Journal of Organic Chemistry. 17, 1939-1951. [CrossRef]
  3. Uriarte, I., Reviriego, F., Calabrese, C., Elguero, J., Kisiel, Z., Alkorta, I.E., Cocinero, E.J. (2019). Bond length alternation observed experimentally: The case of 1H-indazole. European Journal of Medicinal Chemistry, 25, 10172. [CrossRef]
  4. Hunt, K.W., Moreno, D.A., Suiter, N., Clark, C.T., Kim, G. (2009). Selective synthesis of 1-functionalized-alkyl-1H-indazoles. Organic Letters 11(21), 5054-5057. [CrossRef]
  5. Alkorta, I., Elguero, J. (2005). Theoretical estimation of the annular tautomerism of indazoles. Journal of Physical Organic Chemistry, 18, 719-724. [CrossRef]
  6. Doganc, F., Göker, H. (2024). Differentiation of regioisomeric N-alkylation of some indazoles and pyrazolopyridines by advanced NMR techniques. Magnetic Resonance in Chemistry, 62, 765-774. [CrossRef]
  7. 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. [CrossRef]
  8. Puskullu, M.O., Doganc, F., Ozden, S., Sahin, E., Celik, I., Göker, H. (2021). Synthesis, NMR, X-ray crystallography and DFT studies of some regioisomers possessing imidazole heterocycles. Journal of Molecular Structure, 1243, 130811. [CrossRef]
  9. Karaaslan, C., Doganc, F., Alp, M., Koc, A., Karabay, A.Z., Göker, H. (2020). Regioselective N-alkylation of some imidazole-containing heterocycles and their in vitro anticancer evaluation. Journal of Molecular Structure, 1205, 127673. [CrossRef]
  10. Göker, H., Özden, S. (2019). Regioselective N-alkylation of 2-(3,4-dimethoxyphenyl)imidazo[4,5-b] and [4,5-c]pyridine oxide derivatives: Synthesis and structure elucidation by NMR. Journal of Molecular Structure, 1197, 183-195. [CrossRef]
  11. Bulygina, L.A., Khrushcheva, N.S., Klemenkova, Z.S., Lyssenko, K.A., Peregudov, A.S., Solokov, V.I. (2018). Journal of Organometallic Chemistry, 867, 391-397. [CrossRef]