Various types of 1-hydroxyindoles were prepared for the first time.Through methylation or acid catalyzed nucleophilic bromination of N,N-dimethyl-1 -hydroxytryptamine, simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine were achieved, respectively.~espedaminez (1 a, Scheme 1) was isolated from Lespedeza bicolorvar.japonica Nakai and -b r o m o -~, ~-d i m e t h ~l t r y ~t a m i...
A general synthetic method of 4-substituted indoles was examined.The Fischer indolization of phenylhydrazones (2, 3, 7, and 8) having chlorine on & position gave 7-chloro-4-substituted indoles (4, 9, and lo), which were converted to 4-substituted indoles (5 and 13) by catalytic hydrogenation.Cyclization of 3-(2-ethoxy~arbonyl-7-chloroindol-4-yl)propionic acid (10) with polyphosphoric acid (PPA)...