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Total synthesis of a B‐ring “homoalkaloid”. 4,5,6,7,7a,8‐Hexahydro‐7‐methylphenanthro[10,1‐ bc ]azepine
Author(s) -
Jensen Bruce L.,
Woods Michael A.
Publication year - 1979
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.5570160705
Subject(s) - azepine , chemistry , diborane , benzazepine , yield (engineering) , ring (chemistry) , total synthesis , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , boron , materials science , metallurgy
The synthesis of a novel benzazepine, 4,5,6,7,7a,8‐hexahydro‐7‐methylphenanthro[10,1‐ bc ]‐azepine, is described. Two pathways leading from 1,2,4,5‐tetrahydro‐1‐( o ‐nitrophenyl)‐3 H ‐2‐benzazepin‐3‐one were investigated. The most successful route, utilizing a Pschorr cyclization followed by diborane reduction and Eschweiler‐Clarke methylation, led to an excellent yield of the title compound.