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The synthesis of perloline, 6-(3,4-Dimethoxyphenyl)-5-hydroxy-5,6-dihydrobenzo[c]-[2,7]naphthyridin-4(3H)-one

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Prager, R.H. and Were, S. T. (1983) The synthesis of perloline, 6-(3,4-Dimethoxyphenyl)-5-hydroxy-5,6-dihydrobenzo[c]-[2,7]naphthyridin-4(3H)-one. Australian Journal of Chemistry, 36 (7). pp. 1441-1453.


Article Link: https://doi.org/10.1071/CH9831441

Publisher URL: https://www.publish.csiro.au/paper/CH9831441


Dehydroperloline is obtained in high overall yield by an intramolecular cyclization of the benzyne generated from 4-(2-bromophenyl)-N-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (21), by use of lithium hexamethyldisilazide. A benzyne intermediate has not been established. The pyridinone (21) was prepared in three steps from 2-[1-(2-bromophenyl)ethylidene]malononitrile. Dehydroperloline was smoothly reduced by sodium bis(methoxyethoxy)aluminium hydride to perloline, isolated as its hydrochloride.

Item Type:Article
Business groups:Biosecurity Queensland
Additional Information:Reproduced with permission from © CSIRO Publishing. Access to published version is available via Publisher’s website.
Subjects:Science > Biology > Biochemistry
Agriculture > Agriculture (General) > Agricultural chemistry. Agricultural chemicals
Live Archive:26 Jul 2021 23:52
Last Modified:03 Sep 2021 16:46

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