[1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions
Previously unknown 3,4‐diamino‐1,2,5‐selenadiazole (6) was prepared by hydrolysis of [1,2,5]selenadiazolo[3,4‐c][1,2,5]selenadiazole (7b) and used in synthesis of novel 1,2,5‐selenadiazolo[3,4‐b]pyrazines by the Koerner–Hinsberg reaction covering the parent compound 4 and its substituted derivatives...
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Published in: | European journal of organic chemistry 2015-09, Vol.2015 (25), p.5585-5593 |
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Main Authors: | , , , , , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
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Online Access: | Get full text |
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Summary: | Previously unknown 3,4‐diamino‐1,2,5‐selenadiazole (6) was prepared by hydrolysis of [1,2,5]selenadiazolo[3,4‐c][1,2,5]selenadiazole (7b) and used in synthesis of novel 1,2,5‐selenadiazolo[3,4‐b]pyrazines by the Koerner–Hinsberg reaction covering the parent compound 4 and its substituted derivatives 5a–g. The compounds synthesized were characterized by solution and solid‐state 77Se NMR, and 6, 5‐Ph and 5,6‐Me2[1,2,5]selenadiazolo[3,4‐b]pyrazines (5a, g, respectively) by X‐ray diffraction. Electrochemical reduction of 5,6‐R2[1,2,5]selenadiazolo[3,4‐b]pyrazines 5c, g (R = Ph, Me) into novel persistent radical anions (RAs) was studied by cyclic voltammetry and the RAs [5c]– and [5g]– were characterized by EPR spectroscopy combined with DFT calculations.
3,4‐Diamino‐1,2,5‐selenadiazole was synthesized and used for preparing novel [1,2,5]selenadiazolo[3,4‐b]pyrazines. Electrochemical reduction of the latter into persistent radical anions (RAs) was studied by CV and the RAs were characterized by EPR combined with DFT calculations. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201500742 |