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Morphanthridines II. 11‐aminoalkyl‐5,6‐dihydromorphanthridines
Author(s) -
Drukker Alexander E.,
Judd Claude I.,
Spoerl Joan M.,
Kaminski Frank E.
Publication year - 1965
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.5570020312
Subject(s) - chemistry , halide , lithium (medication) , cleavage (geology) , medicinal chemistry , catalytic hydrogenation , ring (chemistry) , ion , catalysis , stereochemistry , organic chemistry , medicine , geotechnical engineering , fracture (geology) , engineering , endocrinology
Butyl lithium converts 5‐substituted‐5,6‐dihydromorphanthridines to the 11‐position anion. Treatment of this lithium anion with aminoalkyl halides affords the 11‐aminoalkylated derivatives. Catalytic hydrogenation causes reductive cleavage of benzylamino bridge of the morphanthridine ring, a reaction which is used to structurally relate these compounds to the known 11‐aminoalkylidene‐5, 6‐dihydromorphanthridines