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The synthesis of a series of (α‐amino)indol‐3‐yl ketones
Author(s) -
Sanchez Joseph P.,
Parcell Robert F.
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250222
Subject(s) - chemistry , formic acid , halogenation , sodium azide , tetrahydrofuran , hydrogen bromide , bromine , ethyl formate , wolff rearrangement , dimethylformamide , organic chemistry , acetic acid , yield (engineering) , medicinal chemistry , bromide , chloroform , ketene , materials science , solvent , metallurgy
A series of [(α‐amino)indol‐3‐yl]‐2‐methyl‐1‐propanones and [(α‐amino)indol‐3‐yl]cyclopentylmethanones has been synthesized by a variety of reductive reactions performed on the corresponding series of (α‐azido)‐indol‐3‐yl ketones. One of the more interesting reductive procedures involved the palladium‐catalyzed decomposition of formic acid with the formation of hydrogen in situ. The (α‐azido)ketones were prepared in excellent yield by the displacement of the tertiary bromine atom from the (α‐bromo)ketones using sodium azide in N,N ‐dimethylformamide. Bromination was accomplished by using either cupric bromide in ethyl acetate/chloroform or phenyltrimethylammonium tribromide in tetrahydrofuran.