2020
DOI: 10.1021/acs.joc.0c01586
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Ring Expansion of 2-Azido-2-phenyl-indan-1,3-dione for the Generation of Heterocyclic Scaffolds

Abstract: A novel ring expansion based on the readily available 2-azido-2-phenyl-indan-1,3-dione is described. Treatment with primary amines and cesium carbonate in a two-step sequence gives rise to 3-amino-2,3-dihydroisoquinoline-1,4-diones with an unprecedented substitution pattern. The corresponding conversion using amino acid methyl esters leads directly to a novel tricyclic 1,10a-dihydroimidazo-isoquinoline-2,5,10-trione scaffold, a structure that has never been reported before, to the best of our knowledge.

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