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

Akpinar D. E., YAKUT M., Aslan H., ALAGÖZ O., Oktemer A., DAL H., ...More

SYNTHETIC COMMUNICATIONS, vol.48, no.19, pp.2510-2521, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 48 Issue: 19
  • Publication Date: 2018
  • Doi Number: 10.1080/00397911.2018.1509094
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.2510-2521
  • Keywords: Benzopyran, benzofuran, spiro[4.5]decane, cyclization, manganese(III) acetate, CERIUM(IV) AMMONIUM-NITRATE, ELECTRON-RICH ALKENES, MANGANESE(III) ACETATE, CLAISEN REARRANGEMENT, RADICAL CYCLIZATION, BIOLOGICAL-ACTIVITY, RING EXPANSION, DIHYDROPYRANS, DERIVATIVES, 3-OXOPROPANENITRILES
  • Anadolu University Affiliated: Yes

Abstract

In this study, the radical cyclization reactions of cyclic 1,3-dicarbonyl compounds (1a-c) and a, b-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-en2-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.