English

Zibaseresht R,Amirloo Mr,Mohit Azar S,Azimi M,Karimi P

doi:10.9735/0975-3699.5.1.153-158

Abstract

An improved multistep synthetic route for preparation of a tridentate terpyridyl ligand, 2-(pyrid-2΄-yl)-1,10-phenanthroline, has been reported. In the first step, a Skraup quinoline synthesis using m-toluidine and glycerol was employed. The mixture of 5- and 7-methylquinoline which was obtained was selectively nitrated at 8-carbon position of the 7- derivative. The methyl group in 7-methyl-8-nitroquinoline was then oxidized to an aldehyde followed by a reduction of the nitro group to an amine group. The last step involved a Friedlander condensation of the amino aldehyde with 2-acetylpyridine to obtain the final product with overall high yield. All products were fully characterized.

Highlights

Oligopyridines and 2,2’:6’,2’’-terpyridine in particular, have received considerable attention in supramolecular chemistry [1].As it has been reflected in the literature, substituted 2,2’:6’,2’’terpyridines are promising building blocks for supramolecular systems [2] and there is great interest in their coordination with transition metals, [3,4,5,6,7,8] mainly due to their interesting photophysical properties [9,10] and potential pharmaceutical applications [11,12]
The work of most groups has been concerned with attaching functional groups directly to the C(4’) of 2,2’:6’,2’’-terpyridine [14,15,16,17,18,19,20,21,22,23,24], principally, because of the ease of synthesis of the substituted terpyridine from the related aldehyde
The key step of the synthesis was to prepare 7-methyl quinoline as a starting material

Summary

Introduction

Oligopyridines and 2,2’:6’,2’’-terpyridine (tpy) in particular, have received considerable attention in supramolecular chemistry [1].As it has been reflected in the literature, substituted 2,2’:6’,2’’terpyridines are promising building blocks for supramolecular systems [2] and there is great interest in their coordination with transition metals, [3,4,5,6,7,8] mainly due to their interesting photophysical properties [9,10] and potential pharmaceutical applications [11,12]. The resulting oil was further purified using vacuum distillation: bp 91oC (3 mmHg) to give a 70% yield of 7-Methylquinoline (based on GC-MS and 1H NMR).

Results

Conclusion