EN
Synthesis and Structural Characterization of New Benzimidazole Compounds Derived from Electron-Rich Olefins Bearing 1,4- Bisbenzimidazole with CS2, PhNCS, and Chalcogens
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 1H NMR, 13C
NMR, FTIR spectroscopic techniques and elemental analysis.
Keywords
References
- 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.
Details
Primary Language
English
Subjects
Chemical Engineering
Journal Section
Research Article
Publication Date
September 1, 2018
Submission Date
July 24, 2018
Acceptance Date
September 4, 2018
Published in Issue
Year 2018 Volume: 5 Number: 3
APA
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, 5(3), 1037-1042. https://doi.org/10.18596/jotcsa.447056
AMA
1.Yılmaz Ü, Küçükbay H. Synthesis and Structural Characterization of New Benzimidazole Compounds Derived from Electron-Rich Olefins Bearing 1,4- Bisbenzimidazole with CS2, PhNCS, and Chalcogens. JOTCSA. 2018;5(3):1037-1042. doi:10.18596/jotcsa.447056
Chicago
Yılmaz, Ülkü, and Hasan Küçükbay. 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 5 (3): 1037-42. https://doi.org/10.18596/jotcsa.447056.
EndNote
Yılmaz Ü, Küçükbay H (September 1, 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 5 3 1037–1042.
IEEE
[1]Ü. Yılmaz and H. Küçükbay, “Synthesis and Structural Characterization of New Benzimidazole Compounds Derived from Electron-Rich Olefins Bearing 1,4- Bisbenzimidazole with CS2, PhNCS, and Chalcogens”, JOTCSA, vol. 5, no. 3, pp. 1037–1042, Sept. 2018, doi: 10.18596/jotcsa.447056.
ISNAD
Yılmaz, Ülkü - Küçükbay, Hasan. “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 5/3 (September 1, 2018): 1037-1042. https://doi.org/10.18596/jotcsa.447056.
JAMA
1.Yılmaz Ü, Küçükbay H. Synthesis and Structural Characterization of New Benzimidazole Compounds Derived from Electron-Rich Olefins Bearing 1,4- Bisbenzimidazole with CS2, PhNCS, and Chalcogens. JOTCSA. 2018;5:1037–1042.
MLA
Yılmaz, Ülkü, and Hasan Küçükbay. “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, vol. 5, no. 3, Sept. 2018, pp. 1037-42, doi:10.18596/jotcsa.447056.
Vancouver
1.Ülkü Yılmaz, Hasan Küçükbay. Synthesis and Structural Characterization of New Benzimidazole Compounds Derived from Electron-Rich Olefins Bearing 1,4- Bisbenzimidazole with CS2, PhNCS, and Chalcogens. JOTCSA. 2018 Sep. 1;5(3):1037-42. doi:10.18596/jotcsa.447056
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