Facile Synthesis of 1,6-Bis(2-furyl)-2,5-bis(2-hydroxy-3-formyl-5-methylbenzyl)-2,5-diazahexane: a New Dinucleating Ligand

Abstract

A convenient three-step preparation of the dinucleating ligand, 1,6-bis(2-furyl)-2,5-bis(2-hydroxy-3-formyl-5-methylbenzyl)-2,5-diazahexane (3) starting from 2,6-bis(hydroxymethyl)-4-methylphenol (4) is reported. Compound 4 was partially oxidized with preactivated manganese dioxide to form compound 5, which was converted to 2-hydroxy-3-chloromethyl-5-ethylbenzaldehyde (6) with conc.HCl/EtOH. Compound 6 in turn reacted with N,N’-bis (2-furyl)-1,2-diaminoethane (7) in the presence of K2CO3 in ethanol to give the title compound 3. No protecting groups were required in the whole process and the conditions were mild.

Asymmetric zinc(ii) complexes as functional and structural models for phosphoesterases

“…29,37 Merrifield resin (1% crosslinked, 3.5 mmol g −1 Cl) was obtained from Aldrich Chemical Company (microanalysis found C 80.18, H 6.64%).…”

1,6-Bis(2-furyl)-2,5-bis(3-formyl-2-hydroxy-5-methylbenzyl)-2,5-diazahexane

“…All commercially available reagents were used as supplied. The title compound was synthesized by the reaction of 1,6-bis(2-furyl)-2,5diazahexane and 2-hydroxy-3-(chloromethyl)-5-methylbenzaldehyde (molar ratio 1:2.2) in the presence of K 2 CO 3 in ethanol solution for 6 h at 313 K (Sun et al, 2001). Colorless crystals suitable for X-ray determination were obtained by slowly evaporating the ethanol solution at room temperature for about three weeks.…”

Bis(N,N′-di-2-furylethane-1,2-diamine-κ2N,N′)bis(perchlorato-κO)copper(II)

“…For related literature, see: Akitsu & Einaga (2003); Hori et al (2001); Karunakaran & Kandaswamy (1994); McCollum et al (1994); Rameau (1938); Sun et al (2001).…”