Synthesis of a Novel Library of 1-Substituted Pyrido[1,2-a]benzimidazoles

Satyanarayana Gadde; Yun Cheuk Leung; Mohan Bhadbade; Belamy B. Cheung; David StC. Black; Naresh Kumar

doi:10.1071/CH20173

RESEARCH ARTICLE (Open Access)

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Synthesis of a Novel Library of 1-Substituted Pyrido[1,2-a]benzimidazoles

Satyanarayana Gadde ^A ^B , Yun Cheuk Leung ^A , Mohan Bhadbade ^A , Belamy B. Cheung ^B ^C , David StC. Black

^A ^D and Naresh Kumar

^A ^D

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.

^B Children’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales, Sydney, NSW 2052, Australia.

^C School of Women’s and Children’s Health, The University of New South Wales, Sydney, Randwick, NSW 2031, Australia.

^D Corresponding authors. Email: d.black@unsw.edu.au; n.kumar@unsw.edu.au

Australian Journal of Chemistry 73(12) 1208-1218 https://doi.org/10.1071/CH20173
Submitted: 30 May 2020 Accepted: 30 July 2020 Published: 28 August 2020

Journal Compilation © CSIRO 2020 Open Access CC BY-NC-ND

Abstract

The reactivity and synthesis of new analogues of pyrido[1,2-a]benzimidazoles have been explored. Twenty-three derivatives bearing phenoxy, thiophenoxy, aniline, and aryl groups at the 1-position were successfully synthesised in 25–91 % yield, via nucleophilic substitution, Buchwald–Hartwig amination, and Suzuki coupling type processes. Solvent free synthetic protocols were employed to achieve the nucleophilic substitution of anilines with electron donating groups or moderately electron withdrawing groups on a sterically demanding intermediate (7a). An unusual polycyclic heterocycle was identified as a side-product during this work: a dimeric bis(pyrido[1,2-a]benzimidazole).

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