Sequential, Electrochemical‐Photochemical Synthesis of 1,2,4‐Triazolo‐[4,3‐a]pyrazines

1,2,4‐triazolo‐[4,3‐a]pyrazine was prepared via a two‐step electrochemical, photochemical process. First, a 5‐substituted tetrazole is electrochemically coupled to 2,6‐dimethoxypyrazine to yield 1,5‐ and 2,5‐ disubstituted tetrazoles. Subsequent photochemical excitation of the 2,5‐disubstituted tetr...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-06, Vol.30 (31), p.e202400661-n/a
Main Authors: Yount, Joseph, Morris, Megan, Henson, Noah, Zeller, Matthias, Byrd, Edward F. C., Piercey, Davin G.
Format: Article
Language:English
Subjects:
Electrochemistry
Energetic materials
energetics
nitrilimine
pharmaceuticals
Photochemicals
photochemistry
Pyrazine
Pyrazines
Tetrazoles
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Summary:1,2,4‐triazolo‐[4,3‐a]pyrazine was prepared via a two‐step electrochemical, photochemical process. First, a 5‐substituted tetrazole is electrochemically coupled to 2,6‐dimethoxypyrazine to yield 1,5‐ and 2,5‐ disubstituted tetrazoles. Subsequent photochemical excitation of the 2,5‐disubstituted tetrazole species using an ultraviolet lamp releases nitrogen gas and produces a short‐lived nitrilimine intermediate. Subsequent cyclization of the nitrilimine intermediate yields a 1,2,4‐triazolo‐[4,3‐a]pyrazine backbone. The scope of this reaction was explored using various tetrazoles and pyrazines. Materials produced were identified using chemical analytical techniques and computationally studied for potential application as an insensitive energetic material. The electrochemical coupling of tetrazole species with 2,6‐dimethoxypyrazine, followed by UV cyclization has resulted in an effective means for the synthesis of 1,2,4‐triazolo‐[4,3‐a]pyrazine.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202400661