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New benz[g]indole and spiroketone heterocycles from acyl thioacetamides
Author(s) -
Marten E. Hoffmeister,
Maggiulli C. A.
Publication year - 1978
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.5570150807
Subject(s) - chemistry , indole test , yield (engineering) , organic chemistry , stereochemistry , metallurgy , materials science
The acyl thioacetanilide 3 condensed with 2‐bromotetralone to give the spiroketone 5 . A similar reaction of the tetralone with the acyl‐ N ‐ethylthioacetamide 4 afforded small amounts of the unsaturated spiroketone 6 with the isomeric dihydrobenz[ g ]indole 7 as the major product. Compound 7 was aromatized to the benz[ g ]indole 8 in high yield.
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