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Paper | Regular issue | Vol 75, No. 4, 2008, pp.871-877
Published online, 18th January, 2008
DOI: 10.3987/COM-07-11281
Synthesis and Properties of 3,3’-Polymethylene-2,2’-bibenzo[b]-1,10-phenanthrolines

A. F. M. Motiur Rahman and Yurngdong Jahng*

*College of Pharmacy, Yeungnam University, Gyeongsan 712-749, Korea

Abstract

The Friedländer reactions of 4-aminoacridine-3-carbaldehyde with cyclcoalkane-1,2-diones were examined. The reactions of cycloheptane- and cycloocatane-1,2-diones afforded 3,3’-tri- and 3,3’-tetramethylene-2-(pyrid-2’-yl)benzo[b]-1,10-phenanthrolines in 20% and 80%, respectively, while reactions with butane-2,3-dione, cyclopentane-1,2-dione and cyclohexane-1,2-dione afforded only unexpected benzo[b]-1,10-phenanthroline. The trimethylene-bridge is flexible at room temperature while the tetramethylene units are rigid enough to magnetically differentiate all the 8 aliphatic protons at room temperature in NMR time scale even though showing two aliphatic carbon resonaces as expected.