Synthetic strategies to a telomere-targeted pentacyclic heteroaromatic salt

被引：22

作者：

Hutchinson, Ian ^{[1
]}

Stevens, Malcolm F. G. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Pharm, Ctr Biomol Sci, Nottingham NG7 2RD, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2007年 / 5卷 / 01期

关键词：

D O I：

10.1039/b613580n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three routes have been explored to synthesise the telomere-targeted agent 3,11-difluoro-6,8,13-trimethyl-8H-quino[4,3,2-kl] acridinium methosulfate 3. Application of a 6-(2-azidophenyl) phenanthridine precursor 11 gave an entry to the indazolo[2,3-f] phenanthridine ring system 12 not the required quino[ 4,3,2-kl] acridine. A six step synthesis starting from 2,6- dibromo-4-methylbenzonitrile 13 via a 1-arylacridin-9(10H)-one intermediate, 19 or 21, gave the required 3 in low overall yield (< 10%). The most efficient route entailed the one-pot (five step) conversion of 1,2-dimethyl-6-fluoroquinolinium methosulfate 23 to 3 in 33% yield employing triethylamine as base and nitrobenzene as solvent.

引用

页码：114 / 120

页数：7

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