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The preparation and reduction of 5‐cyano‐3‐indolylketones. Synthesis of 5‐cyanotryptamines
Author(s) -
Degraw Joseph I.,
Kennedy Jill G.,
Skinner W. A.
Publication year - 1966
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.5570030103
Subject(s) - chemistry , sodium borohydride , yield (engineering) , acylation , cleavage (geology) , catalysis , chloride , organic chemistry , borohydride , sodium , combinatorial chemistry , medicinal chemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
The acylation of indoles under acidic conditions has been studied. Stannic chloride was shown to be an effective catalyst for the preparation of some 3‐acylindoles, notably 5‐cyano‐3‐indolylketones. The various 5‐cyano ‐3 ‐ indolylketones were reduced with sodium borohydride to yield either the 5‐cyano‐3‐carbinols or 5‐cyano‐3‐alkylindoles. 5‐Cyanotryptamines were obtained by reduction of appropriate α‐dialkylamino and α‐azidoketones. A cleavage reaction of the carbinols involving loss of the 3‐side chain to yield 5‐cyanoindole is also described.