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

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Duong, T., Prager, R.H. and Were, S. T. (1983) A 'biogenetic like' 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. 1431-1440.

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Article Link(s): https://doi.org/10.1071/CH9831431

Publisher URL: https://www.publish.csiro.au/paper/CH9831431

Abstract

9H-Indeno[2,1-c]pyridine-1(2H),9-dione, prepared by a new efficient route, reacts with 3,4-dimethoxy- phenyllithium to form the keto alcohol (7), which rearranges with hydrazoic acid to form 5-(3,4- dimethoxyphenyl)benz[c][2,7]naphthyridin-4(3H)-one. The N-oxide photolyses smoothly to yield dehydroperloline as the sole product.

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
Deposited On:26 Jul 2021 23:54
Last Modified:03 Sep 2021 16:46

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