[1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selena­diazole and Generation of Persistent Radical Anions

[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 Vol. 2015; no. 25; pp. 5585 - 5593
Main Authors: Konstantinova, Lidia S., Bobkova, Irina E., Nelyubina, Yulia V., Chulanova, Elena A., Irtegova, Irina G., Vasilieva, Nadezhda V., Camacho, Paula S., Ashbrook, Sharon E., Hua, Guoxiong, Slawin, Alexandra M. Z., Woollins, J. Derek, Zibarev, Andrey V., Rakitin, Oleg A.
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 01-09-2015
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects:
Cyclovoltammetry
DFT calculations
EPR spectroscopy
Nitrogen heterocycles
Radical anions
Selenium heterocycles
Synthetic methods
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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.
Bibliography:istex:DB74E47E29DE5C8DBF1EBEF4D408A2A4DB5073D4
ark:/67375/WNG-9W6HRX0K-J
ArticleID:EJOC201500742
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500742