Synthesis and characterization of piperazine-substituted dihydrofuran derivatives viaMn(OAc)3 mediated radical cyclizations


SARI S. , YILMAZ M.

TURKISH JOURNAL OF CHEMISTRY, vol.44, no.5, pp.1303-1332, 2020 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 44 Issue: 5
  • Publication Date: 2020
  • Doi Number: 10.3906/kim-2003-23
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.1303-1332
  • Keywords: Piperazine, dihydrofuran, Mn(OAc)(3), radical cyclization, CERIUM(IV) AMMONIUM-NITRATE, FLUORINATED 1,3-DICARBONYL COMPOUNDS, MANGANESE(III) ACETATE, STEREOSELECTIVE-SYNTHESIS, BIOLOGICAL EVALUATION, 3-OXOPROPANENITRILES, ALKENES, HETEROCYCLES, ALKYLATION, DESIGN

Abstract

The aim of this study is to synthesize novel piperazine-containing dihydrofuran compounds (3a-n)from radical additions and cyclizations of diacyl and alkyl-acyl piperazine derivatives (1a-h) with 1,3-dicarbonyl compounds (2a-c) mediated by Mn(OAc)(3) for the first time. From the reactions of 1a-c with dimedone (2a);1a, 1c, and 1d with acetylacetone (2b); and la with ethylacetoacetate(2c) ,the dihydrofuran-piperazine compounds 3a-c > 3d-f, and 3g were obtained in medium to high yields (31%-81%), respectively. In addition, dihydrofuran-piperazine compounds 3h-j and 3k-n were prepared at low to medium yields (20%-40%) from the reactions of le-g with 2a and 1e-h with 2c, respectively.