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ChemInform Abstract: Practical Synthesis of 4-Chloro-2-(2-naphthyl)quinoline, a Precursor to Triple-Helix DNA Intercalators.

✍ Scribed by L. STREKOWSKI; O. ZEGROCKA; C. WINDHAM; A. CZARNY

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199807162

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✦ Synopsis

Practical Synthesis of 4-Chloro-2-(2-naphthyl)quinoline, a Precursor to Triple-Helix DNA Intercalators. -Use of phosphorus pentachloride in a mixture with phosphorus oxychloride improves the efficiency of the last reaction step in the synthesis of title compound (V) from 75% to 86% yield. Nucleophilic displacement of chloride in (V), facilitated by complexation of ring N-atom with Lewis acid tin tetrachloride, leads to amino derivatives, e.g. (VIII) (27% overall yield from (I)), the desired triplex DNA intercalators.

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