Phenanthridines functionalized in the C-ring have been synthesized by IMDAF (intramolecular Diels-Alder reaction on furans) cyclization of ortho-furyl(alkenylamino)arenes under both microwave and conventional heating conditions. The outcomes of the reactions are highly dependent on the substitution patterns both on the dienophile and on the arene components. 5,6-Dihydrophenanthridines, which can easily be oxidized to fully aromatic phenanthridines, are formed
The results of the intramolecular reactions of substrates (I) and (VII) are highly dependent on the substituents and on the reaction conditions. Initially formed Diels-Alder adducts such as (III) and (VIII) are transformed into alcohols, ketones, or oxidized to fully aromatic phenanthridine (VI). -(GULBRANDSEN, H. S.; HENNUM, M.; OSHEKA, M.; READ, M. L.; GUNDERSEN*, L.-L.; Eur. J. Org. Chem. 2014, 36, 8182-8190, http://dx.
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