
%0 Journal Article
%A Elmes, BC 
%A Swan, JM 
%T Synthesis of 6-Oxaellipticine, 5,11-Dimethylbenzofuro[2,3-g]isoquinoline, and related heterocycles
%J Australian Journal of Chemistry
%D 1969/09/01
%V 22
%N 9
%P 1963-1974
%K 
%R https://doi.org/10.1071/CH9691963
%U https://www.publish.csiro.au/paper/CH9691963 
%X 6-Oxaellipticine, 5,11-dimethylbenzofuro[2,3-g]isoquinoline, has been synthesized by a three-step procedure from 1,4-dimethyldibenzofuran utilizing a Pomeranz-Fritsch cyclization. The structures of the intermediate 2-formyl-1,4-dimethyldibenzofuran and of 6-oxaellipticine were confirmed by application of the nuclear Overhauser effect. The parent heterocycle, benzofuro[2,3-g]isoquinoline, has been prepared similarly from dibenzofuran, and this product converted successively into 2-methylbenzofuro[2,3-g]isoquinolinium iodide, 2-methyl-1,2,3,4- tetra-hydrobenzofuro[2,3-g]isoquinoline, and 2-methyl-1-oxo-1,2,3,4- tetrahydrobenzofuro-[2,3-g]isoquinoline.     Benzothieno[3,2-h]isoquinoline has been prepared from 4- formyldibenzo-thiophen formed together with the 2-formyl derivative by reaction of dibenzothiophen with dichloromethyl methyl ether in the presence of stannic chloride. 
