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

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.

[1]  E. Apohan,et al.  Synthesis and Evaluation of Novel Benzimidazole Conjugates Incorporating Amino Acids and Dipeptide Moieties , 2017 .

[2]  Ülkü Yılmaz,et al.  Synthesis and characterization of novel phosphoramidates containing benzimidazole moiety , 2016 .

[3]  M. Tahir,et al.  Synthesis, microwave‐promoted catalytic activity in Suzuki–Miyaura cross‐coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group , 2011 .

[4]  V. Lynch,et al.  Synthesis and study of differentially substituted dibenzotetraazafulvalenes. , 2007, Organic letters.

[5]  Lionel Delaude,et al.  Imidazol(in)ium-2-carboxylates as N-heterocyclic carbene precursors in ruthenium–arene catalysts for olefin metathesis and cyclopropanation , 2006 .

[6]  Lionel Delaude,et al.  Imidazol(in)ium carboxylates as N-heterocyclic carbene ligand precursors for Suzuki-Miyaura reactions , 2006 .

[7]  Andrew J Boydston,et al.  Synthesis and study of Janus bis(carbene)s and their transition-metal complexes. , 2006, Angewandte Chemie.

[8]  M. Lappert.  Contributions to the Chemistry of Carbenemetal Chemistry. , 2006 .

[9]  F. Hahn,et al.  Spirocyclic diaminocarbenes: synthesis, coordination chemistry, and investigation of their dimerization behavior. , 2005, Chemistry.

[10]  R. Durmaz,et al.  Synthesis and Antibacterial Activities of New Bis-benzimidazoles , 2004, Arzneimittelforschung.

[11]  F. Hahn,et al.  Simple access to unsymmetrically substituted, saturated N-heterocyclic carbenes. , 2003, Angewandte Chemie.

[12]  R. Durmaz,et al.  Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds. , 2003, Farmaco.

[13]  H. Fiebig,et al.  2‐benzoxazolyl and 2‐benzimidazolyl hydrazones derived from 2‐acetylpyridine: A novel class of antitumor agents , 2001, International journal of cancer.

[14]  J. Lown,,et al.  Bis-benzimidazole anticancer agents: targeting human tumour helicases. , 1999, Anti-cancer drug design.

[15]  R. Durmaz,et al.  Synthesis and antimicrobial activity of electron rich olefin derived cyclic ureas. , 1996, Arzneimittel-Forschung.

[16]  P. Dixneuf,et al.  New (Carbene)ruthenium−Arene Complexes: Preparation and Uses in Catalytic Synthesis of Furans† , 1996 .

[17]  R. Durmaz,et al.  Synthesis and antimicrobial activity of substituted benzimidazole, benzothiazole and imidazole derivatives. , 1995, Arzneimittel-Forschung.

[18]  H. Güneş,et al.  Synthesis of some hydroxamic acid derivatives of benzimidazole and their antibacterial and antifungal activities. , 1992, Arzneimittel-Forschung.

[19]  M. Lappert.  The coordination chemistry of electron-rich alkenes (enetetramines) , 1988 .

[20]  J. Hocker,et al.  Reactions of Electron‐Rich Olefins with Proton‐Active Compounds , 1972 .

[21]  J. B. Wright.  The chemistry of the benzimidazoles. , 1951, Chemical reviews.

[22]  R. L. Thompson.  The effect of metabolites, metabolite antagonists and enzyme-inhibitors on the growth of the vaccinia virus in Maitland type of tissue cultures. , 1947, Federation proceedings.

[23]  J. Lown,,et al.  Design, synthesis and antitumor cytotoxicity of novel bis-benzimidazoles. , 2000, Anti-cancer drug design.

[24]  M. Lappert,et al.  A new class of benzoin condensation catalyst, the bi-(1,3-dialkylimidazolidin-2-ylidenes) , 1982 .

[25]  J. Pedley,et al.  Photoelectron spectra of electron-rich olefins and an isostructural boron compound; olefins of exceptionally low first ionisation potential , 1971 .