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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

[1,4]Benzodioxino[2,3-g]isoquinolines and [1,4]Dioxinodiisoquinolines

EJ Browne

Australian Journal of Chemistry 28(8) 1803 - 1811
Published: 1975

Abstract

Examples of the new ring systems [1,4]benzodioxino[2,3-g]isoquinoline, [1,4]dioxino[2,3-g:5,6-g?]di-isoquinoline and [1,4]dioxino[2,3-g:6,5- g?]diisoquinoline have been prepared. A route starting with chloromethylation of dibenzo[b,e][1,4]dioxin (1a) yielded a reduced tetracyclic derivative (2b) and mixed isomeric reduced pentacyclic derivatives (3b) and (4b). The latter differed in the p.m.r. resonances arising from the protons in positions 5, 7, 12 and 14. Initial di- chloromethylation of (1a) had thus occurred in both the 2,7- and 2,8- positions, whereas acylation normally gives only 2,7-disubstitution. The pentacyclic compound (3b) was prepared unambiguously from 2,7- dimethyl-dibenzo[b,e][1,4]dioxin. A low yield of the fully aromatized tetracyclic compound (2) was obtained by Pictet-Gams cyclization of N- {2-(dibenzo[b,e][1,4]dioxin-2-yl)-2-hydroxyethyl}benzamide.

https://doi.org/10.1071/CH9751803

© CSIRO 1975

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