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A Concise Synthesis to Benzo[ c ]cinnolines via 2,2’‐Dinitro‐1,1’‐Biphenyls Attained from a Novel Tailored Suzuki Cross‐Coupling
Author(s) -
Elumalai Vijayaragavan,
Bjørsvik HansRené
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701993
Subject(s) - cinnoline , intramolecular force , suzuki reaction , diazo , chemistry , sonogashira coupling , biphenyl , nitro , combinatorial chemistry , functional group , stereochemistry , medicinal chemistry , organic chemistry , palladium , catalysis , alkyl , polymer
A new two‐step synthetic process for the preparation of unsymmetrically substituted benzo[ c ]cinnolines was developed. The key intermediate 2,2’‐dinitro‐1,1’‐biphenyl was prepared by means of an unprecedented tailored Suzuki cross‐coupling protocol. The subsequent step is constituted by a domino partial nitro group reduction and intramolecular diazo bond formation, a process that afford target benzo[ c ]cinnoline scaffold. The disclosed method tolerates both electron‐withdrawing‐ and electron‐donating groups.