Research Article
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Year 2018, , 1037 - 1042, 01.09.2018
https://doi.org/10.18596/jotcsa.447056

Abstract

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.
  • 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.

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

Year 2018, , 1037 - 1042, 01.09.2018
https://doi.org/10.18596/jotcsa.447056

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.

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.
  • 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.
There are 30 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Ülkü Yılmaz 0000-0002-2806-4781

Hasan Küçükbay

Publication Date September 1, 2018
Submission Date July 24, 2018
Acceptance Date September 4, 2018
Published in Issue Year 2018

Cite

Vancouver 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):1037-42.