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Studies on the benzo[1,2]cyclohepta[3,4,5‐d,e]isoquinoline ring system
Author(s) -
Humber L. G.,
Davis M. A.,
Thomas R. A.,
Otson R.,
Watson J. R.
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.5570030301
Subject(s) - chemistry , isoquinoline , cycloheptene , methylamine , ring (chemistry) , medicinal chemistry , stereochemistry , amine gas treating , organic chemistry
Abstract The syntheses of various oxidation states of the novel benzo[1, 2]cyclohepta[3, 4, 5‐d, e]‐isoquinoline ring system is described. The ring system was obtained by the Schmidt rearrangement, with exclusive alkyl migration, of 1, 6, 7, 11b‐tetrahydro ‐ 2 H ‐ dibenz‐[cd,h]azulen‐2‐one and by a Bischler‐Napieralski reaction of suitable derivatives of 10, 11‐dihydro‐5 H ‐dibenzo[a, d]cycloheptene ‐ 5 ‐ methylamine. 4, 5, 10, 11 ‐ Tetramethoxy derivatives of the new ring system were best prepared by a Pictet‐Spengler reaction of the appropriate amine.