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Morphanthridines III . 6‐Basic substituted morphanthridines
Author(s) -
Drukker Alexander E.,
Judd Claude I.,
Dusterhoft Donald D.
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.5570030220
Subject(s) - chemistry , halide , butyllithium , ring (chemistry) , medicinal chemistry , ion , grignard reaction , organic chemistry , stereochemistry , reagent
Abstract The reaction of hydrazines and amines with 6‐chloromorphanthridine was investigated. Grignard coupling of aminoalkyl halides with 6‐chloromorphanthridine afforded 6‐amino‐alkylmorphanthridines. Cyclization of 6‐(2‐chloroethylamino)morphanthridine yielded the new ring system 5′ H ‐imidazo[5, 6‐a]dibenz[b, ejazepine, which was aminoalkylated by generation of the 11‐position anion with butyllithium, followed by treatment with a tertiary aminoalkyl halide.