Synthesis and characterization of salen-type ligands functionalized with pyrrole derivative pendant arms

• Type: Article in International Scientific Journal
• Date: 2005

Authors

Andrade, M (Author) Other; Sousa, C (Author) Other; Borges, JE (Author) FCUP; Freire, C (Author) FCUP

Journal

Title: Journal of Physical Organic Chemistry

Vol. 18

Pages: 935-940

ISSN: 0894-3230

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 7 Citations

Scopus - 7 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-000-1N8

DOI: 10.1002/poc.924

Abstract (EN): Several salen-type ligands functionalized with two pyrrole derivative pendant arms were prepared. These Schiff base ligands, which differ in the imine bridge, were prepared by a multi-step procedure that includes (i) synthesis of 3-pyrrol-1-ylpropanoic acid, (ii) transformation of the latter compound into the mixed carboxylic-carbonic anhydride (MCCA) intermediate followed by reaction with 2,3-dihydroxybenzaidehyde to give (3-formyl-2-hydroxyphenyl) 3-(pyrrol-1-yl)propanoate and finally (iii) Schiff condensation of the different 1,2-diamines with (3-formyl-2-hydroxyphenyl) 3-(pyffol-1-yl)propanoate. The key step in the Schiff base ligand preparation is the functionalization of the 2,3-dihydroxybenzaldehyde at the C-3 hydroxyl group without protection of the C-2 hydroxyl group, by a regiospecific acylation of the ortho-hydroxyl group via esterification with the mixed carboxylic-carbonic anhydride of 3-pyrrol-1-ylpropanoic acid. The compounds were characterized by elemental analyses, H-1 and C-13 NMR spectroscopy, mass spectrometry and FTIR and UV-visible spectrophotometry. Copyright (c) 2005 John Wiley & Sons, Ltd.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 6