D-Fructose-Derived Acetonide as a Green Neutral Organocatalyst for Proficient One-Pot and Three-Component Preparation of 1,3-Benzoxazine Monomers


YILDIRIM A., Goker M.

CHEMISTRYSELECT, vol.5, no.23, pp.6971-6977, 2020 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 5 Issue: 23
  • Publication Date: 2020
  • Doi Number: 10.1002/slct.202001911
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded, Scopus, Academic Search Premier
  • Page Numbers: pp.6971-6977
  • Keywords: Benzoxazine, Monomer, Multicomponent reactions, Organocatalysis, Synthetic methods, FULLY BIOBASED BENZOXAZINES, RING-OPENING POLYMERIZATION, DIAMINE-BASED BENZOXAZINES, CATALYZED SYNTHESIS, PHENOLIC MATERIALS, ALDOL REACTIONS, NAPHTHOXAZINES, CONDENSATION, DERIVATIVES, ALDEHYDES

Abstract

A series of 1,3-benzoxazine monomers were successfully synthesized by simple one-pot and three-component condensation of phenol, paraformaldehyde and varying types of primary aliphatic and aromatic amines in a molar ratio of 1 : 2 : 1 and in the presence of non-acidic 2,3;4,5-di-O-isopropylidene-beta-D-fructopyranose as an effective green carbohydrate based organocatalyst obtained from renewable feedstock. This multicomponent method provides a convenient fast approach for the construction of valuable 1,3-benzoxazine monomers (8 examples) with moderate to excellent yields. The chemical structures of the synthesized benzoxazines were confirmed by FTIR,H-1 NMR,C-13 NMR spectra and elemental analysis.