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New Aryl Derivatives of Quinolinedione and Related Heterocyclic Compounds
Author(s) -
Egu Samuel Attah,
Okoro Uchechukwu Chris,
Onoabedje Efeturi Abraham
Publication year - 2017
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.2745
Subject(s) - chemistry , quinoline , aryl , boronic acid , palladium , heck reaction , coupling reaction , suzuki reaction , combinatorial chemistry , reaction conditions , organic chemistry , catalysis , medicinal chemistry , alkyl
The synthesis of new derivatives of 6,7‐dibromoquinoline‐5,8‐dione and 6,7‐dichloroquinoline‐5,8‐dione via palladium/Sphos‐mediated Suzuki–Miyaura cross‐coupling reaction is reported. The 6,7‐dibromoquinoline‐5,8‐dione and 6,7‐dichloroquinoline‐5,8‐dione intermediates were prepared in a three‐step reaction from 8‐hydroxyquinoline. The palladium‐catalyzed reactions of 6,7‐dibromoquinoline‐5,8‐dione and 6,7‐dichloroquinoline‐5,8‐dione with a variety of aryl boronic acids provide coupled compounds in high yields. The arylation of 6,7‐dibromoquinoline‐5,8‐dione and 6,7‐dichloroquinoline‐5,8‐dione with 4‐bromophenyl boronic acid supplied 6,6′‐(1,4‐phenylene)bis(7‐bromoquinoline‐5,8‐dione) and (4‐(6‐(4‐(6‐chloro‐5,8‐dihydroquinolin‐7‐yl)phenyl)‐5,8‐dihydroquinolin‐7‐yl)phenyl)boronic acid respectively, in addition to the expected coupled compounds in moderate yields. Also, Pd(0)/PPh 3 allowed the 7‐chloro‐6‐(4‐nitrophenyl)quinoline‐5,8‐dione and 7‐chloro‐6‐phenylquinoline‐5,8‐dione to be synthesized via Heck reaction . The yields of the synthesized target molecules depend largely on the reaction conditions and the type of ligands employed. Structural assignments of the synthesized compounds were established by spectra and analytical data.