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Ring-degenerate rearrangement resulting from the azo coupling reaction of a 3-aryl-1,3a,6a-triazapentalene

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The 3-(4-(methoxycarbonyl)phenyl)triazapentalene is a highly fluorescent small molecule which is readily accessible via a two-step synthesis. In the search for postfunctionalization methods, a radical CH-arylation with diazonium salts was attempted. However, azo coupling resulted in a ring-degenerate rearrangement toward a 2-aryl-4-azotriazapentalene, which was confirmed via crystallographic analysis. A mechanism involving the generation of a nitrilimine is proposed. In addition, reduction of the azo group led to cleavage of the triazapentalene core. The present results further demonstrate the sensitivity of the triazapentalene fluorophore.
Tijdschrift: Journal of Organic Chemistry
ISSN: 0022-3263
Issue: 14
Volume: 84
Pagina's: 9434 - 9439
Jaar van publicatie:2020