
TY  - JOUR
A1  - Browne, EJ 
T1  - [1,4]Benzodioxino[2,3-g]isoquinolines and [1,4]Dioxinodiisoquinolines
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1975
VL  - 28
IS  - 8
SP  - 1803
EP  - 1811
KW  - 
UR  - https://doi.org/10.1071/CH9751803 
N2  - 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. 
ER  -

