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

✍ Scribed by Eduardo Cortés Cortés; Concepcién Lozada García; Karla Sánchez Montes; Rubén Sánchez Obregón; Sandra Cortez Maya; Olivia García Mellado De Cortés

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2007
• Tongue: English
• Weight: 530 KB
• Volume: 44
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570440107

✦ Synopsis

Abstract

magnified image

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.