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

Year 2011, Issue: 2, 85 - 96, 01.06.2011

Nezire Saygılı

Abstract

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.

Keywords

Heterobiaril cross-coupling metallasyon sentez

References

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  • McCarthy, M., Guiry, P. J. : Axially Chiral Bidentate Ligands in Asymmetric Cataly- sis, Review Article, Tetrahedron, 57(18), 3809 (2001).
  • Shirota, Y. : Organic Materials for Electronic and Optoelectronic Devices, J. Mater. Chem., 10, 1-25 (2000).
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  • Westmark, P. R., Smith, B. D. : Boronic Acids Selectively Facilitate Glucose Transport through a Lipid Bilayer, J. Am. Chem. Soc., 116, 9343-9344 (1994).
  • 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
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  • 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).
  • Trecourt, F., Queguiner, G. : Synthesis of Xanthones and Thioxanthones Having 2 Het- eroaromatic Rings, Journal of Chemical Researchs, 3, 76-77 (1982).
  • 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).
  • 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).
  • Cai, D., Larsen, R. D., Reider, P. J., Effective Lithiation of 3-Bromopyridine: Synthesis of 3-Pyridine Boronic Acid and Variously 3-Substituted Pyridines, Tetrahedron Letters, 43(23), 4285-4287 (2002).
  • Bouillon, A., Lancelot, J. C., Collot, V., Bovy, P. R., Rault, S. : Synthesis of Novel Halo- pyridinylboronic Acids and Esters. Part 1: 6-Halopyridin-3-yl-boronic Acids and Esters, Tetrahedron, 58(14), 2885-2890 (2002).
  • Bouillon, A., Lancelot, J. C., Collot, V., Bovy, P. R., Rault, S. : Synthesis of Novel Halo- pyridinylboronic Acids and Esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic Acids and Esters, Tetrahedron, 58(17), 3323-3328 (2002).
  • Anctil, E. J. G., Snieckus, V. : The Directed ortho Metalation-Cross Coupling Symbiosis. Regioselective Methodologies for Biaryls and Heterobiaryls. Deployment in Aromatic and Heteroaromatic Natural Product Synthesis, Journal of Organometallic Chemistry, 653, 150–160 (2002).
  • Mohler, L. K., Czarnik, A. W. : Ribonucleoside Membrane Transport by a New Class of Synthetic Carrier, J. Am. Chem. Soc., 115(7), 2998-2999 (1993).
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  • Thompson, A. E., Batsanov, A. S., Bryce, M. R., Saygili, N., Parry, P. R., Tarbit, B. : 2-Ethoxy-3-pyridylboronic acid: A Versatile Reagent for the Synthesis of Highly-Func- tionalised 3-Aryl/heteroaryl-pyridines via Suzuki Cross-coupling Reactions, Tetrahe- dron, 61(21), 4873-5140 (2005).
  • Demir, A. S., Fındık, H., Saygili, N., Subaşı, N. T. : Manganese (III) acetate Mediated Synthesis of Biaryls Under Microwave Irradiation, Tetrahedron, 66, 1308-1312 (2010).
  • Parry, P. R., Bryce, M. R., Tarbit, B. : New Shelf-Stable Halo- and Alkoxy-Substituted Pyridiylboronic Acids and their Suzuki Cross-Coupling Reactions to Yield Heteroaryl- pyridines, Synthesis, 7, 1035-1038 (2003).
  • Thompson, A. E., Hughes, G., Batsanov, A. S., Bryce, M. R., Parry, P. R., Tarbit, B. : Palladium-Catalyzed Cross-Coupling Reactions of Pyridylboronic Acids with Heteroaryl Halides Bearing a Primary Amine Group: Synthesis of Highly Substituted Bipyridines and Pyrazinopyridines, Journal of Organic Chemistry, 70(1), 388-390 (2005).
  • Y. Shirota : Organic Materials for Electronic and Optoelectronic Devices, J. Mater. Chem., 10(1), 1-25 (2000).
  • Wang, C., Jung, G. Y., Batsanov, A. S., Bryce, M. R., Petty, M. C. : New electron-trans- porting materials for light emitting diodes: 1,3,4-oxadiazole-pyridine and 1,3,4-oxadia- zole-pyrimidine hybrids, J. Mater. Chem., 12(2), 173-180 (2002).
  • Mitschke, U., Bäuerle, P. : The electroluminescence of organic materials, J. Mater. Chem., 10(7), 1471-1507 (2000).
  • Lock, E. A., John, I. : The acute toxic effects of paraquat and diquat on the rat kidney, Toxicology and Applied Pharmacology, 50(1), 67-76 (1979).
  • Revkin, A. C. : Paraquat: A potent weed killer is killing people, Science Digest, 91(6), 36-38 References and further reading may be available for this article. To view references and further reading you must purchase this artic(1983).
  • Mandal, S., Moudgil, M., Mandal, S. : Rational drug design, European Journal of Phar- macology, 625(1-3), 90–100 (2009).
  • Manley, P., Stiefl, N., Cowan-Jacob, S., Kaufman, S., Mestan, J., Wartmann, M., Wi- esmann, M., Woodman, R. : Structural resemblances and comparisons of the relative pharmacological properties of imatinib and nilotinib, Bioorganic & Medicinal Chemis- try, 18(19), 6977–6986 (2010).

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

Year 2011, Issue: 2, 85 - 96, 01.06.2011

Nezire Saygılı

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.

Keywords

Heterobiaryl cross-coupling metallation synthesis

References

  • Thomas, L. Gilchrist, Heterocyclic Chemistry, Addison Wesley Longman Ltd., Third Edition, 262 (1997).
  • Cass, Q. B., Tiritan, E., Matlin, S. A., Freire, E. C. : Gossypol enantiomer ratios in cot- ton seeds, Phytochemistry, 30(8), 2655-2657 (1991).
  • McCarthy, M., Guiry, P. J. : Axially Chiral Bidentate Ligands in Asymmetric Cataly- sis, Review Article, Tetrahedron, 57(18), 3809 (2001).
  • Shirota, Y. : Organic Materials for Electronic and Optoelectronic Devices, J. Mater. Chem., 10, 1-25 (2000).
  • Stanforth, S. P. : Catalytic Cross-Coupling Reactions in Biaryl Synthesis, Review Ar- ticle, Tetrahedron, 54(3-4), 263-303 (1998).
  • Miyaura, N., Suzuki, A. : Palladium-Catalyzed Cross-Coupling Reactions of Organobo- ron Compounds, Chem. Rev., 95, 2457-2483 (1995).
  • Suzuki, A. : Recent Advances in the Cross-Coupling Reactions of Organoboron Deriva- tives with Organic Electrophiles, 1995–1998 Review Article, J. Organometallic Chem- sitry, 576(1-2), 147-168 (1999).
  • Westmark, P. R., Smith, B. D. : Boronic Acids Selectively Facilitate Glucose Transport through a Lipid Bilayer, J. Am. Chem. Soc., 116, 9343-9344 (1994).
  • 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).
  • 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).
  • 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).
  • Trecourt, F., Queguiner, G. : Synthesis of Xanthones and Thioxanthones Having 2 Het- eroaromatic Rings, Journal of Chemical Researchs, 3, 76-77 (1982).
  • 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).
  • 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).
  • Cai, D., Larsen, R. D., Reider, P. J., Effective Lithiation of 3-Bromopyridine: Synthesis of 3-Pyridine Boronic Acid and Variously 3-Substituted Pyridines, Tetrahedron Letters, 43(23), 4285-4287 (2002).
  • Bouillon, A., Lancelot, J. C., Collot, V., Bovy, P. R., Rault, S. : Synthesis of Novel Halo- pyridinylboronic Acids and Esters. Part 1: 6-Halopyridin-3-yl-boronic Acids and Esters, Tetrahedron, 58(14), 2885-2890 (2002).
  • Bouillon, A., Lancelot, J. C., Collot, V., Bovy, P. R., Rault, S. : Synthesis of Novel Halo- pyridinylboronic Acids and Esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic Acids and Esters, Tetrahedron, 58(17), 3323-3328 (2002).
  • Anctil, E. J. G., Snieckus, V. : The Directed ortho Metalation-Cross Coupling Symbiosis. Regioselective Methodologies for Biaryls and Heterobiaryls. Deployment in Aromatic and Heteroaromatic Natural Product Synthesis, Journal of Organometallic Chemistry, 653, 150–160 (2002).
  • Mohler, L. K., Czarnik, A. W. : Ribonucleoside Membrane Transport by a New Class of Synthetic Carrier, J. Am. Chem. Soc., 115(7), 2998-2999 (1993).
  • Saygili, N., Batsanov, A. S., Bryce, M. R. : 5-Pyrimidylboronic Acid and 2-Methoxy-5- pyrimidylboronic Acid: New Heteroarylpyrimidine Derivatives via Suzuki Cross-cou- pling Reactions, Org. Biomol. Chem., 2, 852-857 (2004).
  • Thompson, A. E., Batsanov, A. S., Bryce, M. R., Saygili, N., Parry, P. R., Tarbit, B. : 2-Ethoxy-3-pyridylboronic acid: A Versatile Reagent for the Synthesis of Highly-Func- tionalised 3-Aryl/heteroaryl-pyridines via Suzuki Cross-coupling Reactions, Tetrahe- dron, 61(21), 4873-5140 (2005).
  • Demir, A. S., Fındık, H., Saygili, N., Subaşı, N. T. : Manganese (III) acetate Mediated Synthesis of Biaryls Under Microwave Irradiation, Tetrahedron, 66, 1308-1312 (2010).
  • Parry, P. R., Bryce, M. R., Tarbit, B. : New Shelf-Stable Halo- and Alkoxy-Substituted Pyridiylboronic Acids and their Suzuki Cross-Coupling Reactions to Yield Heteroaryl- pyridines, Synthesis, 7, 1035-1038 (2003).
  • Thompson, A. E., Hughes, G., Batsanov, A. S., Bryce, M. R., Parry, P. R., Tarbit, B. : Palladium-Catalyzed Cross-Coupling Reactions of Pyridylboronic Acids with Heteroaryl Halides Bearing a Primary Amine Group: Synthesis of Highly Substituted Bipyridines and Pyrazinopyridines, Journal of Organic Chemistry, 70(1), 388-390 (2005).
  • Y. Shirota : Organic Materials for Electronic and Optoelectronic Devices, J. Mater. Chem., 10(1), 1-25 (2000).
  • Wang, C., Jung, G. Y., Batsanov, A. S., Bryce, M. R., Petty, M. C. : New electron-trans- porting materials for light emitting diodes: 1,3,4-oxadiazole-pyridine and 1,3,4-oxadia- zole-pyrimidine hybrids, J. Mater. Chem., 12(2), 173-180 (2002).
  • Mitschke, U., Bäuerle, P. : The electroluminescence of organic materials, J. Mater. Chem., 10(7), 1471-1507 (2000).
  • Lock, E. A., John, I. : The acute toxic effects of paraquat and diquat on the rat kidney, Toxicology and Applied Pharmacology, 50(1), 67-76 (1979).
  • Revkin, A. C. : Paraquat: A potent weed killer is killing people, Science Digest, 91(6), 36-38 References and further reading may be available for this article. To view references and further reading you must purchase this artic(1983).
  • Mandal, S., Moudgil, M., Mandal, S. : Rational drug design, European Journal of Phar- macology, 625(1-3), 90–100 (2009).
  • Manley, P., Stiefl, N., Cowan-Jacob, S., Kaufman, S., Mestan, J., Wartmann, M., Wi- esmann, M., Woodman, R. : Structural resemblances and comparisons of the relative pharmacological properties of imatinib and nilotinib, Bioorganic & Medicinal Chemis- try, 18(19), 6977–6986 (2010).
There are 32 citations in total.

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Primary Language English
Journal Section Research Article
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Nezire Saygılı

Publication Date June 1, 2011
Published in Issue Year 2011 Issue: 2

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Vancouver Saygılı N. New Pyridinylboronic Acid and New Heterobiaryls via Cross-Coupling Reactions of Pyridinylboronic Acids with Heteroaryl Halides. HUJPHARM. 2011(2):85-96.