SavedAdd your journal

Journals / Journal of the Turkish Chemical Society Section A: Chemistry / 2018 / Volume: 5 Issue: 3

Synthesis and Structural Characterization of New Benzimidazole Compounds Derived from Electron-Rich Olefins Bearing 1,4- Bisbenzimidazole with CS2, PhNCS, and Chalcogens

Ülkü Yılmaz(İnönü Üniversitesi)0000-0002-2806-4781
Hasan Küçükbay
Pages
—
Publication Date
2018-09-01
🏛️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)

The chemical structure of novel benzimidazole compounds were determined by 1 H NMR, 13 C NMR, FTIR spectroscopic techniques and elemental analysis.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In this work, 1,4-bis(3-isopropylbenzimidazolidine-2-ylidene-1-yl)butane ( 1 ) and 1,4-bis(3,5(6)-dimethylbenzimidazolidine-2-ylidene-1-yl)butane ( 2 ) were reacted with oxygen, sulfur, selenium, tellurium, phenyl isothiocyanate and carbon disulfur.
📊
Key Findings & Data:New zwitterionic compounds ( 9 - 12 ) and cyclic urea derivatives of benzimidazole as one ( 3 ), thione ( 4 , 6 ), selenone ( 5 , 7 ), tellurone ( 8 ) were synthesised from electron-rich olefins.
💡
Conclusion & Impact:The chemical structure of novel benzimidazole compounds were determined by 1 H NMR, 13 C NMR, FTIR spectroscopic techniques and elemental analysis.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Bisbenzimidazole · electron rich olefin · strong nucleophile

Abstract

In this work, 1,4-bis(3-isopropylbenzimidazolidine-2-ylidene-1-yl)butane ( 1 ) and 1,4-bis(3,5(6)-dimethylbenzimidazolidine-2-ylidene-1-yl)butane ( 2 ) were reacted with oxygen, sulfur, selenium, tellurium, phenyl isothiocyanate and carbon disulfur. New zwitterionic compounds ( 9 - 12 ) and cyclic urea derivatives of benzimidazole as one ( 3 ), thione ( 4 , 6 ), selenone ( 5 , 7 ), tellurone ( 8 ) were synthesised from electron-rich olefins. The chemical structure of novel benzimidazole compounds were determined by 1 H NMR, 13 C NMR, FTIR spectroscopic techniques and elemental analysis.

🔖

Cite This Article

Yılmaz, Ü., Küçükbay, H. (2018). Synthesis and Structural Characterization of New Benzimidazole Compounds Derived from Electron-Rich Olefins Bearing 1,4- Bisbenzimidazole with CS2, PhNCS, and Chalcogens. Journal of the Turkish Chemical Society Section A: Chemistry, Volume: 5 Issue: 3. https://doi.org/10.18596/jotcsa.447056

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (30)

  1. Easmon J, Puerstinger G, Roth T, Fiebig HH, Jenny M, Jaeger W, Heinisch G, Hoffmann J. 2-Benzoxazolyl and 2-benzimidazolyl hydrazones derived from 2-acetylpyridine: A novel class of antitumor agents. Int J Cancer. 2001;94:89-96.
  2. Güneş HS and Cosar G. Synthesis of some hyroxamic acid-derivatives of benzimidazole and their antibacterial and antifungal activities. Arzneim-Forsch/Drug Res. 1992;42-2(8):1045-1048.
  3. Küçükbay H, Durmaz R, Orhan E, Günal S. Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds. Il Farmaco. 2003;58:431-437.
  4. Yılmaz Ü, Küçükbay H, Şireci N, Akkurt M, Günal S, Durmaz R, Tahir MN. Synthesis, microwave-promoted catalytic activity in Suzuki-Miyaura cross-coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group. Appl Organometal Chem. 2011;25(5):366-373.
  5. Küçükbay H. Part I: Microvawe-assisted synthesis of benzimidazoles: An oveview (Until 2013). JOTCSA. 2017; 4(1):1-22.
  6. Buğday N, Küçükbay FZ, Apohan E, Küçükbay H, Serindağ A, Yeşilada Ö. Synthesis and evaluation of novel benzimidazole conjugates incorporating amino acids and dipeptide moieties. Lett Org Chem. 2017; 14(3): 198-206.
  7. Singh AK and Lown JW. Design, synthesis and antitumor citotoxicity of novel bis-benzimidazoles. Anti-Cancer Drug Des. 2000;15(4):265-275.
  8. Soderlind KJ, Gorodetsky B, Singh AK. Bis-benzimidazole anticancer agents: targeting human tumour helicases. Anti-Cancer Drug Des. 1999;14(1):19-36.
  9. Yılmaz Ü, Küçükbay H. Synthesis and characterization of novel phosphoramidates containing benzimidazole moiety. Phosphorus Sulfur Silicon Relat Elem. 2016;191(1):140-143.
  10. Thompson RL. The effectof metabolites, metabolite antagonists, and enzyme inhibitorson the growth of vaccinia virus in Maitland type of tissue cultures. J Immunol. 1947;55:345-352.
  11. Lappert MF. The coordination chemistry of electron-rich alkenes (enetetramines). J Organomet Chem. 1988;358(1-3):185-214.
  12. Çetinkaya B, King GH, Krishnamuthy SS, Lappert MF, Pedley JB. Photoelectron spectra of electron-rich olefins and an isostructural boron compound; olefins of exceptionally low first ionisation potential J Chem Soc D. 1971;1370-1371.
  13. Tudose A, Delaude L, Andre B, Demonceau A. Imidazol(in)ium carboxylates as N-heterocyclic carbene ligand precursors for Suzuki-Miyaura. Tetrahedron Lett. 2006;47(48):8529-8533.
  14. Hahn FE, Paas M., Le Van D, Lugger T. Simple Access to unsymmetrically substituted, saturated N-heterocyclic carbenes. Angew Chem Int Edit. 2003;42(42):5243-5246.
  15. Kamplain JW, Lynch VM, Bielawski CW. Synthesis and study of differantially substituted dibenzotetraazafulvalenes. Org Lett. 2007;9(26):5401-5404.
  16. Küçükbay H, Çetinkaya B, Guesmi S, Dixneuf PH. New (Carbene)ruthenium-arene complexes: preparation and uses in catalytic synthesis of furans. Organometallics. 1996;15:2434-2439.
  17. Vasam CS, and Lin IJB. Silver(I) N-heterocyclic carbenes. Com Inorg Chem. 2004;25(3-4):75-129.
  18. Tudose A, Demonceau A, Delaude L. Imidazol(in)ium-2-carboxylates as N- heterocyclic carbene precursors in ruthenium-arene catalysts for olefin metathesis and cyclopropanation. J Organometal Chem. 2006;691(24-25):5356-5365.
  19. Hahn FE, Paas M., Le Van D, Fröhlic R. Spirocyclic diaminocarbenes: Synthesis, coordination chemistry, and investigation of their dimerization behavior. Chem Eur J. 2005;11:5080-5085.
  20. Khramov DM, Boydston AJ, Bielawski CW. Synthesis and study of janus bis(carbene)s and their transition-metal complexes. Angew Chem Int Edit. 2006;45:6186-6189.
  21. Lappert MF. Contributions to the chemistry of carbenemetal chemistry. J Organometal Chem. 2005;690:5467-5473.
  22. Çetinkaya E, and Küçükbay H. Effective acyloin condensations catalyzed by electron-rich olefins. Turk J Chem. 1995;19:24-30.
  23. Lappert MF, Maskell RK. A new class of benzoin condensation catalyst, the bi-(1,3-dialkylimidazolidin-2-ylidenes). J Chem Soc Chem Commun. 1982;580-581.
  24. Hocker J, and Metren R. Reactions of electron-rich olefins with proton-active compounds. Angew Chem Int Edit. 1972;11:964-973.
  25. Küçükbay H, Çetinkaya E, Çetinkaya B, Lappert MF. Reactions of electron-rich olefins with proton-active compounds. Synth Commun. 1997;27(23):4059-4066.
  26. Çetinkaya B, Çetinkaya E, Küçükbay H, Durmaz R. Synthesis and antimicrobial activity of electron rich olefin derived cyclic ureas. Arzneim-Forsch/Drug Res. 1996;46(12):1154-1158.
  27. Küçükbay H, Durmaz R, Okuyucu N, Günal S, Kazaz C. Synthesis and antibacterial activities of new bis-benzimidazoles. Arzneim-Forsch/Drug Res. 2004;54(1):64-68.
  28. Küçükbay H, Çetinkaya E, Durmaz R. Synthesis and antimicrobial activity of substituted benzimidazole, benzothiazole and imidazole derivatives. Arzneim-Forsch/Drug Res. 1995;45(12):1331-1334.
  29. Li J-Q, Liao R-Z, Ding W-J, Cheng Y. Highly efficient and site-selective [3+2] cycloaddition of carbene-derived ambident dipoles with ketenes for a straightforward synthesis of spiro-pyrrolidons. J Org Chem. 2007;72:6266-6269.
  30. Wright JB. The chemistry of the benzimidazoles. Chem Rev. 1951;48(3):397-541.