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Synthesis of substituted 3‐amino‐4‐cyano‐1‐oxo‐1,2,5,10‐tetrahydroazepino [3,4‐ b ]indoles
Author(s) -
Troschütz Reinhard,
Hoffmann Annin
Publication year - 1997
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.5570340510
Subject(s) - chemistry , aminolysis , sodium borohydride , malononitrile , indole test , medicinal chemistry , condensation , ammonia , alkoxy group , organic chemistry , stereochemistry , catalysis , physics , alkyl , thermodynamics
The preparation of 3‐amino‐ and 3‐dialkylamino‐4‐cyanoazepino[3,4‐fc]indoles bearing substituents on the aromatic nucleus and N 10 is outlined. Starting from suitable substituted ethyl 3‐formylindole‐2‐carboxy‐latcs 2 , condensation with malononitrile ( 3 ) and subsequent sodium borohydride‐reduction yielded ethyl 3‐(2,2‐dicyanoethyl)indole‐2‐carboxylates 5 and 19 , respectively, which were cyclized in boiling alkoxides to 3‐alkoxy‐4‐cyanoazepino[3,4‐ b ]indoles 10,11,20 and 21 . This sequence constitutes a novel and flexible route to functional azepino[3,4‐ b >]indoles. The aminolysis of 10,11,20 and 21 with different amines and ammonia yielded the title compounds which were screened for their possible biological activity.