
%0 Journal Article
%A Gellert, E 
%A Wong, O 
%T Synthesis of dihydroisotryptamines
%J Australian Journal of Chemistry
%D 1984/09/01
%V 37
%N 9
%P 1931-1937
%K 
%R https://doi.org/10.1071/CH9841931
%U https://www.publish.csiro.au/paper/CH9841931 
%X To enable exploration of the physiological activity of isotryptamine derivatives, a number of 1,3-di-hydroisotryptamines, isomers of known tryptamine derivatives possessing significant physiological activity, were synthesized for the first time. Ring-substituted 1-nitrosonaphthalen-2-ols on tosylation and alkaline treatment gave the appropriate (Z)-3-(2'-cyanopheny1)propenoic acids, and by hydration, cyclization and ring-opening these acids were converted into (3'-oxo-1',3'-dihydroisoindol-1'-yl)- acetic acids. Fusion of these products with ureas yielded the corresponding (3'-oxodihydroisoindol-1'-yl)acetamides, which, on simultaneous reduction of the amide and lactam functions by diborane, yielded 1,3-dihydroisotryptamines. Some features of their n.m.r. spectra are also discussed. 
