SavedAdd your journal

Journals / Hacettepe Üniversitesi Eczacılık Fakültesi Dergisi / 2011 / Sayı: 2

New Pyridinylboronic Acid and New Heterobiaryls via Cross-Coupling Reactions of Pyridinylboronic Acids with Heteroaryl Halides

Yeni Piridinilboronik Asit ve Piridinilboronik Asitler ile Heteroaril Halojenürlerin Cross-Coupling Tepkimeleri ile Yeni Heterobiariller

Nezire SAYGILI
Pages
85–96
Publication Date
2011-06-01
DOI
—
🏛️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)

All synthesized compounds were characterized mainly by 1H NMR and 13C NMR spectral data.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:2-Chloro-6-methoxypyridine 9 was lithiated via directed orthometallation DoM reaction with LDA and then treatment with triisopropylborate TIPB afforded 6-chloro-2-methoxypyridin-3-ylboronic acid 12 .
📊
Key Findings & Data:Suzuki Cross-Coupling reaction of this new pyridinyl boronic acid 12 or 2-ethoxypyridin-3-ylboronic acid 18 with various heteroaryl halides gave five new heterobiarys 13-17 .
💡
Conclusion & Impact:All synthesized compounds were characterized mainly by 1H NMR and 13C NMR spectral data.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Heterobiaril · cross-coupling · metallasyon

Abstract

2-Chloro-6-methoxypyridine 9 was lithiated via directed orthometallation DoM reaction with LDA and then treatment with triisopropylborate TIPB afforded 6-chloro-2-methoxypyridin-3-ylboronic acid 12 . Suzuki Cross-Coupling reaction of this new pyridinyl boronic acid 12 or 2-ethoxypyridin-3-ylboronic acid 18 with various heteroaryl halides gave five new heterobiarys 13-17 . All synthesized compounds were characterized mainly by 1H NMR and 13C NMR spectral data.

Özet

2-Klor-6-metoksipiridin 9 , LDA ile orto-metallasyon yönlendirme DoM tepkimesiyle lithiye edildi ve sonra triizopropilborat TIPB ile muamele edilerek 6-klor-2-metoksipiridin-3-ilboronik asit 12 oluşturuldu. Bu yeni piridinil boronik asit 12 veya 2-etoksipiridin-3-ilboronik asitin 18 birçok heteroaril halojenürle Suzuki Cross-Coupling tepkimesi sonucunda beş yeni heterobiaril 13-17 sentezlendi. Tüm sentezlenmiş bileşiklerin yapıları başlıca 1H NMR ve 13C NMR spektral verilerle karakterize edildi.

🔖

Cite This Article

SAYGILI, N. (2011). New Pyridinylboronic Acid and New Heterobiaryls via Cross-Coupling Reactions of Pyridinylboronic Acids with Heteroaryl Halides. Hacettepe Üniversitesi Eczacılık Fakültesi Dergisi, Sayı: 2, 85–96. https://ajindex.com/articles/762388

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (16)

  1. Thomas, L. Gilchrist, Heterocyclic Chemistry, Addison Wesley Longman Ltd., Third Edition, 262 (1997).
  2. Cass, Q. B., Tiritan, E., Matlin, S. A., Freire, E. C.: Gossypol enantiomer ratios in cot- ton seeds, Phytochemistry, 30(8), 2655-2657 (1991).
  3. McCarthy, M., Guiry, P. J.: Axially Chiral Bidentate Ligands in Asymmetric Cataly- sis, Review Article, Tetrahedron, 57(18), 3809 (2001).
  4. Shirota, Y.: Organic Materials for Electronic and Optoelectronic Devices, J. Mater. Chem., 10, 1-25 (2000).
  5. Stanforth, S. P.: Catalytic Cross-Coupling Reactions in Biaryl Synthesis, Review Ar- ticle, Tetrahedron, 54(3-4), 263-303 (1998).
  6. Miyaura, N., Suzuki, A.: Palladium-Catalyzed Cross-Coupling Reactions of Organobo- ron Compounds, Chem. Rev., 95, 2457-2483 (1995).
  7. Suzuki, A.: Recent Advances in the Cross-Coupling Reactions of Organoboron Deriva- tives with Organic Electrophiles, 1995–1998
  8. Review Article, J. Organometallic Chem- sitry, 576(1-2), 147-168 (1999).
  9. Westmark, P. R., Smith, B. D.: Boronic Acids Selectively Facilitate Glucose Transport through a Lipid Bilayer, J. Am. Chem. Soc., 116, 9343-9344 (1994).
  10. James, T. D., Sandanayake, K. R. A. S., Iguchi, R., Shinkai, S.: Novel Saccharide- Photoinduced Electron Transfer Sensors Based on the Interaction of Boronic Acid and Amine, J. Am. Chem. Soc., 117, 8982-8987 (1995).
  11. Weston, G. S., Blazquez, J., Baquero, F., Shoichet, B. K.: Structure-Based Enhance- ment of Boronic Acid-Based Inhibitors of AmpC β-Lactamase, J. Med. Chem., 41, 4577- 4586 (1998).
  12. Gribble, G. W., Saulnier, M. G., Regioselective ortho-Lithiation of Halopyridines. Syn- thesis of ortho-Disubstituted Pyridines and a Convenient Generation of 3,4-Pyridyne, Heterocycles, 35(1), 151-169 (1993).
  13. Trecourt, F., Queguiner, G.: Synthesis of Xanthones and Thioxanthones Having 2 Het- eroaromatic Rings, Journal of Chemical Researchs, 3, 76-77 (1982).
  14. Radinov, R., Haimova, M., Simova, E.: Synthesis of 4-Amino-3-Pyridinyl and 4-Amino- 5-Pyrimidinyl Aryl Ketones and Related Compounds Via an ortho-Lithiation Reaction, Synthesis, 11, 886-891 (1986).
  15. Lamothe, M., Pauwels, P. J., Belliard, K., Schambel, P., Halazy, S.: Differentiation Between Partial Agonists and Neutral 5-HT1B Antagonists by Chemical Modulation of 3-[3-(N,N-dimethylamino)propyl]-4-hydroxy-N-[4-(pyridin-4-yl)phenyl]benzamide (GR- 55562), J. Med. Chem., 40(22), 3542-3550 (1997).
  16. Cai, D., Larsen, R. D., Reider, P. J., Effective Lithiation of 3-Bromopyridine: Synthesis of 3-Pyridine Boronic Acid and Variou