A Novel, Domino Synthesis of Tricyclic Benzimidazole Derivatives Using Continuous Flow

  • Balázs Szabó
    Affiliation

    Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary; Chemical Works of Gedeon Richter Plc., H-1103 Budapest, Gyömrői út 19-21., Hungary

  • Kiara Szakter
    Affiliation

    Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary

  • Angelika Thurner
    Affiliation

    Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary

  • Ferenc Faigl
    Affiliation

    Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary

  • János Éles
    Affiliation

    Chemical Works of Gedeon Richter Plc., H-1103 Budapest, Gyömrői út 19-21., Hungary

  • István Greiner
    Affiliation

    Chemical Works of Gedeon Richter Plc., H-1103 Budapest, Gyömrői út 19-21., Hungary

Abstract

A novel method for synthesis of tricyclic benzimidazole derivatives by using continuous flow reactor is reported. Disadvantages of the well-known batch methods have been avoided utilizing the flow chemistry technology. Beside the one pot reductive cyclization using H-Cube Pro®, the dehydration step was also optimized producing the desired lactam compounds. Then the acylation was optimized under microwave conditions and that reaction was also integrated into the flow system using an Asia heater module. This acylation dramatically reduced the reaction time under continuous-flow conditions, with a residence time of 30 min.

Keywords: benzimidazole, lactam, heterocycles, continuous flow, reductive cyclization, one-pot
Published online
2019-10-17
How to Cite
Szabó, B., Szakter, K., Thurner, A., Faigl, F., Éles, J., Greiner, I. “A Novel, Domino Synthesis of Tricyclic Benzimidazole Derivatives Using Continuous Flow”, Periodica Polytechnica Chemical Engineering, 64(1), pp. 1-8, 2020. https://doi.org/10.3311/PPch.14275
Section
Articles