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