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Synthesis and spectral properties of 7‐( p ‐bromophenyl)‐10,10‐dimethyl‐8‐alkylthio‐7,9,10,11‐tetrahydro‐benz[ c ]acridines and deprotection‐aromatization of 7‐[( o ‐; and p ‐substituted)phenyl]‐10,10‐dimethyl‐7,8,9,10,11,12‐hexahydrobenz[ c ]acridin‐8‐thione
Author(s) -
Cortés Eduardo Cortés,
García Concepcién Lozada,
Montes Karla Sánchez,
Obregón Rubén Sánchez,
Maya Sandra Cortez,
De Cortés Olivia García Mellado
Publication year - 2007
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.5570440107
Subject(s) - chemistry , sodium hydride , aromatization , acridine , reagent , alkylation , methyl iodide , hydride , medicinal chemistry , sodium iodide , alkyl , nitrogen , iodide , sodium , organic chemistry , hydrogen , catalysis
A series of sixteen new derivatives have been obtained and all have potentially useful pharmacological activity. The treatment of 7‐[( o ‐chloro and p ‐bromo)phenyl]‐7,8,9,10,11,12‐hexahydrobenz[ c ]acridin‐8‐one and Lawesson's reagent obtains the corresponding 7‐[( o ‐ and p ‐substituted) phenyl]‐10,10‐dimethyl‐7,8,9,10,11,12‐hexahydrobenz[ c ]acridin‐8‐thione II which was alkylated in presence of sodium hydride and the corresponding alkyl iodide under nitrogen atmosphere to obtain 8‐alkylthio‐7,9,10,11‐tetrahydro‐benz[ c ]acridines III, 1‐4 . The thione II was desprotected and aromatized in presence of sodium hydride in absence of nitrogen atmosphere to produce a mixture of 7‐[( o ‐ and p ‐substituted)phenyl]‐10,10‐dimethyl‐8,9,10,11‐tetrahydrobenz[ c ]‐acridin‐8‐one IV, 1‐6 and 7‐[( o ‐ and p ‐substituted)phenyl]‐10,10‐dimethyl‐8‐hydroxi‐8,9,10,11‐tetrahydrobenz[ c ]acridine V, 1‐6 . The structure of all products was corroborated by ir, 1 H NMR, 13 C NMR with bidimensional experiments and ms with CID experiments.