Tetrazoindazoles: Straightforward Access to Nitrogen‐Rich Polyaromatics from s‐Tetrazines

The straightforward access to a new class of aza‐polyaromatics is reported. Starting from readily available fluorinated s‐tetrazine, a cyclization process with azide leads to the formation of an unprecedented tetrazo[1,2‐b]indazole or a bis‐tetrazo[1,2‐b]indazole (cis and trans conformers). Based on...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-03, Vol.62 (13)
Main Authors: Daher, Ahmad, Bousfiha, Asmae, Tolbatov, Iogann, Mboyi, Clève D, Cattey, Hélène, Roisnel, Thierry, Paul Fleurat‐Lessard, Hissler, Muriel, Jean‐Cyrille Hierso, Pierre‐Antoine Bouit, Julien, Roger
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Fluorescence
Halides
Hydrogen bonds
Molecular structure
Nitrogen
Palladium
Physicochemical properties
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Summary:The straightforward access to a new class of aza‐polyaromatics is reported. Starting from readily available fluorinated s‐tetrazine, a cyclization process with azide leads to the formation of an unprecedented tetrazo[1,2‐b]indazole or a bis‐tetrazo[1,2‐b]indazole (cis and trans conformers). Based on the new nitrogen core, further N‐directed palladium‐catalyzed ortho‐C−H bond functionalization allows the introduction of halides or acetates. The physicochemical properties of these compounds were studied by a joint experimental/theoretical approach. The tetrazo[1,2‐b]indazoles display solid‐state π‐stacking, low reduction potential, absorption in the visible range up to the near‐infrared, and intense fluorescence, depending on the molecular structure.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202300571