Synthesis, characterization, and investigations of antimicrobial activity of benzopyrans, benzofurans and spiro[4.5]decanes

Abstract

In this study, the radical cyclization reactions of cyclic 1,3-dicarbonyl compounds (1a–c) and α,β-unsaturated alcohols (2a–d) through Mn(OAc)₃ were performed. A series of biologically interesting dihydropyrans (3–5) and dihydrofurans (6–18) were synthesized as a result of these reactions. Spiro compounds (19–20) were obtained from the reactions of 1,3-dicarbonyl compounds and (E)-2,4-diphenyl-but-3-en-2-ol (2e). The unique structure of compound 19 was also confirmed by X-ray crystallography. In addition, the antibacterial activities of synthesized compounds were screened against some bacteria. Their zone diameters showed better results than some known antibiotics.

GRAPHICAL ABSTRACT

Keywords:

• Benzopyran
• benzofuran
• spiro[4.5]decane
• cyclization
• manganese(III) acetate

Additional information

Funding

This work was supported by a research grant from the Ankara University BAP [13B4240002].