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Synthesis of 1‐substituted‐2,3,4,9‐tetrahydro‐(2‐oxopropyl)‐1 H ‐pyrido [3,4‐ b ] indoles and their base‐catalyzed rearrangements to N ‐ [2‐[2‐(1‐alkyl‐3‐oxobutenyl)‐1 H ‐indol‐3‐yl] ethyl]acetamides
Author(s) -
Bobowski George
Publication year - 1983
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.5570200202
Subject(s) - chemistry , indole test , catalysis , alkoxide , cleavage (geology) , sodium ethoxide , medicinal chemistry , ring (chemistry) , stereochemistry , ethanol , base (topology) , bond cleavage , organic chemistry , mathematical analysis , mathematics , geotechnical engineering , fracture (geology) , engineering
The condensation of 1 H ‐indole‐3‐ethanamides, 1 , with 2,4‐pentanediones, 2 , gave enamines 3 . Acid catalyzed ring closure of 3 gave 1‐(1‐substituted‐2,3,4,9‐tetrahydro‐ (2‐oxopropyl) ‐1 H ‐pyrido [3,4‐ b ] indoles 4 . Subsequent N ‐acetylation yielded 5 which sequentially produced 2,3‐disubstituted indoles 6 and 7 resulting from CN bond cleavage after treatment with sodium alkoxide in ethanol. Controlled catalytic hydrogenation of the latter gave saturated derivatives 8 and 9 .