Syntheses, spectroscopic and crystallographic characterizations of 4-nitrobenzyloxy derivatives and benzofurans from ortho-substituted benzaldehydes and 4-nitrobenzyl bromide

Hayvali Z., Dal H., Koksal P., Sahin D., HÖKELEK T.

STRUCTURAL CHEMISTRY, vol.21, no.4, pp.837-845, 2010 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 21 Issue: 4
  • Publication Date: 2010
  • Doi Number: 10.1007/s11224-010-9618-6
  • Journal Name: STRUCTURAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.837-845
  • Hacettepe University Affiliated: Yes

Abstract

A series of benzyloxybenzaldehyde derivatives (1-3) were prepared by the reactions of 4-nitrobenzyl bromide with 4-hydroxy-3-methoxybenzaldehyde (vanillin), 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-hydroxy-4-methoxybenzaldehyde. When the reaction time is quite long, benzofuran derivatives (4 and 5) were obtained by the reactions of ortho-hydroxyaldehydes with the 4-nitrobenzyl bromide. Condensation reactions among the three benzyloxybenzaldehyde derivatives (1-3) with 2-aminomethylfuran (furfurylamine) yielded the new imine compounds (6-8). The structures of these aldehydes (1-3), benzofuran derivatives (4 and 5) and imine compounds (6-8) were confirmed on the basis of elemental analyses, IR, (1)H NMR and (13)C NMR and mass spectroscopy. The solid-state structures of compounds 4-6 were determined by single-crystal X-ray crystallography.