SYNTHESIS OF NEW 3-SUBSTITUDED-6-BROMOBENZOXAZOLIN-2-ONE DERIVATIVES

Monika Bertašiūtė1, Vytautas Mickevičius1, Birutė Grybaitė1

1 Department of Organic Chemistry, Faculty of Chemical technology, Kaunas University of Technology, Lithuania

[email protected]

Benzoxazole-based structures play a significant role in medicinal chemistry due to their broad spectrum of biological activities. These fused oxazole-benzene systems exhibit promising antifungal, antibacterial, anti-inflammatory, and anticancer properties.[1, 2, 3] This study focuses on the synthesis of novel benzoxazolinone derivatives with potential biological activity.

The precursor acid was synthesized via bromination of 3-(2-oxobenzo[d]oxazol-3(2H)-yl)propanoic acid in the presence of acetic acid (Fig. 1). The molecular structures of benzimidazole-containing compounds –6 were obtained through the Phillips reaction. Compound was synthesized from precursor using polyphosphoric acid (PPA). To achieve the target acid hydrazide , a standard synthetic pathway - acid to ester to hydrazide - was employed. Finally, hydrazide was condensed with various aromatic aldehydes to introduce the hydrazone moiety –18.

Figure 1
Fig. 1. Synthesis of compounds 2-18

The structure of the synthesized compounds was characterized by spectral data (IR, NMR spectra, and elemental analysis). The spectra showed good agreement with the assigned molecular structures.


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[2] AGGARWAL Nupur, et al. Biologically active Benzoxazole: A comprehensive review. Int. J. Pharm. Sci. Res, 2017, 2.2: 1-5, ISSN: 2455-4685.

[3] SAMIA M. Rida et al. Synthesis of some novel benzoxazole derivatives as anticancer, anti-HIV-1 and antimicrobial agents, European Journal of Medicinal Chemistry, Volume 40, Issue 9, 2005, Pages 949-959. DOI: 10.1016/j.ejmech.2005.03.023.