Microwave-Assisted, Rapid Synthesis of Benzimidazole based Potential Anticancer Agent Methyl 1-benzyl-2-(4-fluoro-3-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate (TJ08) via T3P Mediated Cyclization |
G.S. Jagadeesha1, , N.R. Thimmegowda1,*, , K. Mantelingu2, , D.S. Prasanna3, and K.S. Rangappa4, |
1Department of Chemistry, Government S.K.S.J. Technological Institute (Affiliated to Visvesvaraya Technological University, Karnataka), K.R. Circle, Bangalore-560001, India
2Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570006, India
3Department of Applied Sciences, Visvesvaraya Technological University, Center for Postgraduate Studies, Bengaluru Region, Muddenahalli, Chikkaballapur District-562101, India
4Institution of Excellence, University of Mysore, Mysore-570006, India
*Corresponding author: E-mail: nrthimmegowda@gmail.com |
Abstract A novel microwave assisted protocol for the rapid synthesis of methyl 1-benzyl-2-(4-fluoro-3-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate (TJ08) with potent antileukemic activity has been developed with excellent yields in 31 min of reaction time over 5 steps, whereas the conventional heating method required around 17 h. In this method, n-propanephosphonic acid anhydride (T3P) was used as a coupling reagent for amidation, during this reaction the in situ generated byproduct n-propylphosphonic acid subsequently catalyzes the cyclization reaction to form benzimidazole ring and hence this novel protocol affords to synthesize the novel benzimidazole derivatives expeditiously to develop new druggable compounds. |
Keywords Benzimidazole derivative, T3P, Anticancer agent, Antileukemic activity. |
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