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Year 2019, Volume: 47 Issue: 4, 435 - 442, 01.12.2019
https://doi.org/10.15671/hjbc.550890

Abstract

References

  • 1. Y. Bansal, O. Silakari, The therapeutic journey of benzimidazoles: A review, Bioorg. Med. Chem., 20 (2012) 6208-6236.
  • 2. E. Badawey, T. Kappe, Benzimidazole condensed ring system. IX. Potential antineoplastics. New synthesis of some pyrido[1,2-a]benzimidazoles and related derivative, Eur. J. Med. Chem., 30 (1995) 327-332.
  • 3. A. J. Ndakala, R.K. Gessner, P.W. Gitari, N. October, K.L. White, A. Hudson, F. Fakorede, D.M. Shackleford, M. Kaiser, C. Yeates, S.A. Charman, K. Chibale, Antimalarial pyrido[1,2-a]benzimidazoles, J. Med. Chem., 54 (2011) 4581-4589.
  • 4. M. Hranjec, I. Piantanida, M. Kralj, L. Suman, K. Pavelic, G. Karminski-Zamola, Novel amidino-substituted thienyl- and furylvinylbenzimidazole: derivatives and their photochemical conversion into corresponding diazacyclopenta[c]fluorenes. synthesis, interactions with DNA and RNA, and antitumor evaluation. 4., J. Med. Chem., 51 (2008) 4899-4910.
  • 5. H. Takeshita, J. Watanabe, Y. Kimura, K. Kawakami, H. Takahashi, M. Takemura, A. Kitamura, K. Someya, R. Nakajima, Novel pyridobenzimidazole derivatives exhibiting antifungal activity by the inhibition of beta-1,6-glucan synthesis, Bioorg. Med. Chem. Lett., 20 (2010) 3893-3896.
  • 6. H.L. Koo, H.L. Dupont, Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases, Curr. Opin. Gastroenterol, 26 (2010) 17-25.
  • 7. (a) H.J. Knölker, R. Boese, R. Hitzemann, Imidazole derivatives, III. Regiospecific synthesis,structure, and fluorescence properties of highly substituted imidazo[1,2-a]pyridines and pyrido[1,2-a]benzimidazoles, Chem. Ber., 123 (1990) 327-339.(b) S. Ohta, T. Yuasa, Y. Narita, I. Kawasaki, E. Minamii, M. Yamashita, Synthesis and application of imidazole derivatives. Synthesis of pyrido[l,2-a]benzimidazolone derivatives, Heterocycles, 32 (1991) 1923-1931.(c) H. Schaefer, M. Gruner, G. Grossmann, K. Gewald, On the synthesis and structure of 8-nitro-imidazo[1,2-a]pyridines, Monatsh. Chem., 122 (1991) 959-966.
  • 8. (a) D.B. Zhao, J.Y. Hu, N.J. Wu, X.L. Huang, X.R. Qin, J.B. Lan, J.S. You, Regiospecific synthesis of 1,2-disubstituted (hetero)aryl fused imidazoles with tunable fluorescent emission, Org. Lett., 13 (2011) 6516-6519.(b) T. Iwaki, A. Yasuhara, T. Sakamoto, Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction, J. Chem. Soc., Perkin Trans. 1, 1 (1999) 1505-1510.
  • 9. Z. Wu, Q. Huang, X. Zhou, L. Yu, Z. Li, D. Wu, Synthesis of pyrido[1,2‐a]benzimidazoles through a copper‐catalyzed cascade C-N coupling process, Eur. J. Org. Chem., 2011 (2011) 5242-5245.
  • 10. (a) H. Wang, Y. Wang, C. Peng, J. Zhang, Q. Zhu, A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a]benzimidazoles from N-aryl-2-aminopyridines, J. Am. Chem. Soc., 132 (2010) 13217-13219.(b) K.S. Masters, T.R.M. Rauws, A.K. Yadav, W.A. Herrebout, B. Van der Veken, B. U.W. Maes, On the importance of an acid additive in the synthesis of pyrido[1,2‐a]benzimidazoles by direct copper‐catalyzed amination, Chem. Eur. J., 17 (2011) 6315-6330.(c) D. Liang, Y. He, L. Liu, Q. Zhu, A metal-free tandem demethylenation/C(sp2)-H cycloamination process of N-benzyl-2-aminopyridines via C-C and C-N bond cleavage, Org. Lett., 15 (2013) 3476-3479.(d) S.M. Barolo, Y. Wang, R.A. Rossi, G.D. Cuny, Synthesis of pyrido [1, 2-a] benzimidazoles by photo-stimulated C-N bond formation via S RN 1 reactions, Tetrahedron, 69 (2013) 5487-5494.(e) Y. He, J. Huang, D. Liang, Q. Zhu, C-H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(III) reagent, Chem. Commun., 49 (2013) 7352-7354.(f) D. Rao, S. Rasheed, R. Vishwakarma, P. Das, Hypervalent iodine(III) catalyzed oxidative C-N bond formation in water: synthesis of benzimidazole-fused heterocycles, RSC Adv., 4 (2014) 25600-25604.(g) G. Qian, B. Liu, Q. Tan, S. Zhang, B. Xu, Hypervalent iodine(III) promoted direct synthesis of imidazo[1,2‐a]pyrimidines, Eur. J. Org. Chem., 2014 (2014) 4837-4843.(h) N. Kutsumura, S. Kunimatsu, K. Kagawa, T. Otani, T. Saito, Synthesis of benzimidazole-fused heterocycles by intramolecular oxidative C-N bond formation using hypervalent iodine reagents, Synthesis, 2011 (2011) 3235-3240.
  • 11. S. Manna, K. Matcha, A.P. Antonchick, Metal‐free annulation of arenes with 2‐aminopyridine derivatives: The methyl group as a traceless non‐chelating directing group, Angew. Chem. Int. Ed., 53 (2014) 8163-8166.
  • 12. H. Foks, D. Pancechowska-Ksepko, M. Janowiec, Z. Zwolska, E. Augustynowicz-Kopeé, Synthesis and tuberculostatic activity of some 1,1-bis-methylthio-2-nitro-ethene derivatives, Phosphorus Sulfur, 180 (2005) 2291-2297.
  • 13. M. Yıldırım, D. Celikel, N. Evis, D.W. Knight, B.M. Kariuki, Base-promoted new C-C bond formation: an expedient route for the preparation of thiazolo-and imidazolo-pyridinones via Michael addition, Tetrahedron, 70 (2014) 5674-5681.
  • 14. M. Yıldırım, D. Celikel, Y. Dürüst, D.W. Knight, B.M. Kariuki, A rapid and efficient protocol for the synthesis of novel nitrothiazolo [3, 2-c] pyrimidines via microwave-mediated Mannich cyclisation, Tetrahedron, 70 (2014) 2122-2128.
  • 15. C. Altug, A.K. Burnett, E. Caner, Y. Dürüst, M.C. Elliott, R.P. Glanville, A.D. Westwell, An efficient one-pot multicomponent approach to 5-amino-7-aryl-8-nitrothiazolo [3,2-a] pyridines, Tetrahedron, 67 (2011) 9522-9528.
  • 16. D. Elumalai, R. Gnanasekaran, S. Leelakrishnan, G. Nachimuthu, T. Kannan, T.P. Paramasivam, K. Jayabal, InCl3-assisted eco‐friendly approach for N‐fused 1,4‐dihydropyridine scaffolds via ring opening michael addition of cyclic nitroketene and iminocoumarin: Synthesis and DFT studies, ChemistrySelect, 3 (2018) 2070-2079.

Practical synthesis of pyrido[1,2-a]benzimidazoles via multicomponent reactions

Year 2019, Volume: 47 Issue: 4, 435 - 442, 01.12.2019
https://doi.org/10.15671/hjbc.550890

Abstract

Tek basamakta siklik enamin (2-(nitrometilen)-2,3-dihidro-1H-benzo[d]imidazol),
malononitril ve aromatik aldehit ile çoklu bileşenli tepkime üzerinden 1-amino-3-(4-substitue)-4-nitro-3,5-dihidrobenzo[4,5]imidazo[1,2-a]piridin-2-karbonitril
lerin kolay ve etkili bir biçimde sentezi açığa çıkarıldı. Ayrıca, istenilen
ürünlerin eldesinde herhangi bir saflaştırma prosedürü gerektirmedi. Bütün
ürünler saf olarak tepkime ortamında çökeltildi. On yeni yapı fiziksel ve
spektroskopik yöntemler kullanılarak karakterize edildi (e.n., IR, NMR ve
TOF-MS analizleri).

References

  • 1. Y. Bansal, O. Silakari, The therapeutic journey of benzimidazoles: A review, Bioorg. Med. Chem., 20 (2012) 6208-6236.
  • 2. E. Badawey, T. Kappe, Benzimidazole condensed ring system. IX. Potential antineoplastics. New synthesis of some pyrido[1,2-a]benzimidazoles and related derivative, Eur. J. Med. Chem., 30 (1995) 327-332.
  • 3. A. J. Ndakala, R.K. Gessner, P.W. Gitari, N. October, K.L. White, A. Hudson, F. Fakorede, D.M. Shackleford, M. Kaiser, C. Yeates, S.A. Charman, K. Chibale, Antimalarial pyrido[1,2-a]benzimidazoles, J. Med. Chem., 54 (2011) 4581-4589.
  • 4. M. Hranjec, I. Piantanida, M. Kralj, L. Suman, K. Pavelic, G. Karminski-Zamola, Novel amidino-substituted thienyl- and furylvinylbenzimidazole: derivatives and their photochemical conversion into corresponding diazacyclopenta[c]fluorenes. synthesis, interactions with DNA and RNA, and antitumor evaluation. 4., J. Med. Chem., 51 (2008) 4899-4910.
  • 5. H. Takeshita, J. Watanabe, Y. Kimura, K. Kawakami, H. Takahashi, M. Takemura, A. Kitamura, K. Someya, R. Nakajima, Novel pyridobenzimidazole derivatives exhibiting antifungal activity by the inhibition of beta-1,6-glucan synthesis, Bioorg. Med. Chem. Lett., 20 (2010) 3893-3896.
  • 6. H.L. Koo, H.L. Dupont, Rifaximin: a unique gastrointestinal-selective antibiotic for enteric diseases, Curr. Opin. Gastroenterol, 26 (2010) 17-25.
  • 7. (a) H.J. Knölker, R. Boese, R. Hitzemann, Imidazole derivatives, III. Regiospecific synthesis,structure, and fluorescence properties of highly substituted imidazo[1,2-a]pyridines and pyrido[1,2-a]benzimidazoles, Chem. Ber., 123 (1990) 327-339.(b) S. Ohta, T. Yuasa, Y. Narita, I. Kawasaki, E. Minamii, M. Yamashita, Synthesis and application of imidazole derivatives. Synthesis of pyrido[l,2-a]benzimidazolone derivatives, Heterocycles, 32 (1991) 1923-1931.(c) H. Schaefer, M. Gruner, G. Grossmann, K. Gewald, On the synthesis and structure of 8-nitro-imidazo[1,2-a]pyridines, Monatsh. Chem., 122 (1991) 959-966.
  • 8. (a) D.B. Zhao, J.Y. Hu, N.J. Wu, X.L. Huang, X.R. Qin, J.B. Lan, J.S. You, Regiospecific synthesis of 1,2-disubstituted (hetero)aryl fused imidazoles with tunable fluorescent emission, Org. Lett., 13 (2011) 6516-6519.(b) T. Iwaki, A. Yasuhara, T. Sakamoto, Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction, J. Chem. Soc., Perkin Trans. 1, 1 (1999) 1505-1510.
  • 9. Z. Wu, Q. Huang, X. Zhou, L. Yu, Z. Li, D. Wu, Synthesis of pyrido[1,2‐a]benzimidazoles through a copper‐catalyzed cascade C-N coupling process, Eur. J. Org. Chem., 2011 (2011) 5242-5245.
  • 10. (a) H. Wang, Y. Wang, C. Peng, J. Zhang, Q. Zhu, A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a]benzimidazoles from N-aryl-2-aminopyridines, J. Am. Chem. Soc., 132 (2010) 13217-13219.(b) K.S. Masters, T.R.M. Rauws, A.K. Yadav, W.A. Herrebout, B. Van der Veken, B. U.W. Maes, On the importance of an acid additive in the synthesis of pyrido[1,2‐a]benzimidazoles by direct copper‐catalyzed amination, Chem. Eur. J., 17 (2011) 6315-6330.(c) D. Liang, Y. He, L. Liu, Q. Zhu, A metal-free tandem demethylenation/C(sp2)-H cycloamination process of N-benzyl-2-aminopyridines via C-C and C-N bond cleavage, Org. Lett., 15 (2013) 3476-3479.(d) S.M. Barolo, Y. Wang, R.A. Rossi, G.D. Cuny, Synthesis of pyrido [1, 2-a] benzimidazoles by photo-stimulated C-N bond formation via S RN 1 reactions, Tetrahedron, 69 (2013) 5487-5494.(e) Y. He, J. Huang, D. Liang, Q. Zhu, C-H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(III) reagent, Chem. Commun., 49 (2013) 7352-7354.(f) D. Rao, S. Rasheed, R. Vishwakarma, P. Das, Hypervalent iodine(III) catalyzed oxidative C-N bond formation in water: synthesis of benzimidazole-fused heterocycles, RSC Adv., 4 (2014) 25600-25604.(g) G. Qian, B. Liu, Q. Tan, S. Zhang, B. Xu, Hypervalent iodine(III) promoted direct synthesis of imidazo[1,2‐a]pyrimidines, Eur. J. Org. Chem., 2014 (2014) 4837-4843.(h) N. Kutsumura, S. Kunimatsu, K. Kagawa, T. Otani, T. Saito, Synthesis of benzimidazole-fused heterocycles by intramolecular oxidative C-N bond formation using hypervalent iodine reagents, Synthesis, 2011 (2011) 3235-3240.
  • 11. S. Manna, K. Matcha, A.P. Antonchick, Metal‐free annulation of arenes with 2‐aminopyridine derivatives: The methyl group as a traceless non‐chelating directing group, Angew. Chem. Int. Ed., 53 (2014) 8163-8166.
  • 12. H. Foks, D. Pancechowska-Ksepko, M. Janowiec, Z. Zwolska, E. Augustynowicz-Kopeé, Synthesis and tuberculostatic activity of some 1,1-bis-methylthio-2-nitro-ethene derivatives, Phosphorus Sulfur, 180 (2005) 2291-2297.
  • 13. M. Yıldırım, D. Celikel, N. Evis, D.W. Knight, B.M. Kariuki, Base-promoted new C-C bond formation: an expedient route for the preparation of thiazolo-and imidazolo-pyridinones via Michael addition, Tetrahedron, 70 (2014) 5674-5681.
  • 14. M. Yıldırım, D. Celikel, Y. Dürüst, D.W. Knight, B.M. Kariuki, A rapid and efficient protocol for the synthesis of novel nitrothiazolo [3, 2-c] pyrimidines via microwave-mediated Mannich cyclisation, Tetrahedron, 70 (2014) 2122-2128.
  • 15. C. Altug, A.K. Burnett, E. Caner, Y. Dürüst, M.C. Elliott, R.P. Glanville, A.D. Westwell, An efficient one-pot multicomponent approach to 5-amino-7-aryl-8-nitrothiazolo [3,2-a] pyridines, Tetrahedron, 67 (2011) 9522-9528.
  • 16. D. Elumalai, R. Gnanasekaran, S. Leelakrishnan, G. Nachimuthu, T. Kannan, T.P. Paramasivam, K. Jayabal, InCl3-assisted eco‐friendly approach for N‐fused 1,4‐dihydropyridine scaffolds via ring opening michael addition of cyclic nitroketene and iminocoumarin: Synthesis and DFT studies, ChemistrySelect, 3 (2018) 2070-2079.
There are 16 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Akın Sağırlı 0000-0003-0759-334X

Publication Date December 1, 2019
Acceptance Date September 12, 2019
Published in Issue Year 2019 Volume: 47 Issue: 4

Cite

APA Sağırlı, A. (2019). Practical synthesis of pyrido[1,2-a]benzimidazoles via multicomponent reactions. Hacettepe Journal of Biology and Chemistry, 47(4), 435-442. https://doi.org/10.15671/hjbc.550890
AMA Sağırlı A. Practical synthesis of pyrido[1,2-a]benzimidazoles via multicomponent reactions. HJBC. December 2019;47(4):435-442. doi:10.15671/hjbc.550890
Chicago Sağırlı, Akın. “Practical Synthesis of pyrido[1,2-a]benzimidazoles via Multicomponent Reactions”. Hacettepe Journal of Biology and Chemistry 47, no. 4 (December 2019): 435-42. https://doi.org/10.15671/hjbc.550890.
EndNote Sağırlı A (December 1, 2019) Practical synthesis of pyrido[1,2-a]benzimidazoles via multicomponent reactions. Hacettepe Journal of Biology and Chemistry 47 4 435–442.
IEEE A. Sağırlı, “Practical synthesis of pyrido[1,2-a]benzimidazoles via multicomponent reactions”, HJBC, vol. 47, no. 4, pp. 435–442, 2019, doi: 10.15671/hjbc.550890.
ISNAD Sağırlı, Akın. “Practical Synthesis of pyrido[1,2-a]benzimidazoles via Multicomponent Reactions”. Hacettepe Journal of Biology and Chemistry 47/4 (December 2019), 435-442. https://doi.org/10.15671/hjbc.550890.
JAMA Sağırlı A. Practical synthesis of pyrido[1,2-a]benzimidazoles via multicomponent reactions. HJBC. 2019;47:435–442.
MLA Sağırlı, Akın. “Practical Synthesis of pyrido[1,2-a]benzimidazoles via Multicomponent Reactions”. Hacettepe Journal of Biology and Chemistry, vol. 47, no. 4, 2019, pp. 435-42, doi:10.15671/hjbc.550890.
Vancouver Sağırlı A. Practical synthesis of pyrido[1,2-a]benzimidazoles via multicomponent reactions. HJBC. 2019;47(4):435-42.

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