Iodine-catalyzed synthesis of dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a domino reaction involving double elimination of hydrogen bromide?

Organic & Biomolecular Chemistry Pub Date: 2016-02-03 DOI: 10.1039/C5OB02620B

Abstract

An iodine-catalyzed reaction of 2-aminobenzamides and mucobromic acid was described and utilized to synthesize a variety of 6-oxo-5,6-dihydrodibenzo[b,h][1,6]naphthyridine-11-carboxamide derivatives in refluxing THF. As the two bromine atoms in mucobromic acid were found missing in the dibenzonaphthyridine products, a domino-type reaction mechanism involving a double elimination of hydrogen bromide was proposed.

Graphical abstract: Iodine-catalyzed synthesis of dibenzo[b,h][1,6]naphthyridine-11-carboxamides via a domino reaction involving double elimination of hydrogen bromide
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