Psilocin analogs having either a formyl group (9-12) or a bromine atom (13-18) at the 5- or 7-position have been prepared for the first time. Syntheses of 5- and 7-bromo derivatives of 4-hydroxy- (23, 24, 28) and 4-benzyloxyindole-3-carbaldehyde (19, 25, 29, 30), 4-benzyloxyindole-3-acetonitriles (20, 31), and 4-benzyloxy-N,N-dimethyltryptamine (32, 34, 35) have also been established.
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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...