Beilstein J. Org. Chem.2010,6, No. 45, doi:10.3762/bjoc.6.45
3LE, U.K. GlaxoSmithKline R&D, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire, SG1 2NY, United Kingdom 10.3762/bjoc.6.45 Abstract Reaction of tetrafluoropyridazine with catechol gives a tricyclic 9,10-dioxa-1,2-diaza-anthracene system by a sequential nucleophilic aromatic
substitution ring annelation process, further extending the use of perfluoroheteroaromatic derivatives for the synthesis of unusual polyfunctional heterocyclic architectures. The tricyclic scaffold reacts with amines and sodium ethoxide providing a short series of functional 9,10-dioxa-1,2-diaza-anthracene
systems.
Keywords: benzodioxinopyridazine; 9,10-dioxa-1,2-diaza-anthracene; heterocyclic synthesis; nucleophilic aromatic substitution; perfluoroheteroaromatic; tetrafluoropyrazine; Introduction
Drug discovery programmes are continually searching for viable synthetic routes to highly novel classes of
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Graphical Abstract
Scheme 1:
Synthesis of novel tricyclic heterocycles from pentafluoropyridine.