1,2,5-Selenadiazolo[3,4-b]pyrazines : synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions
Date
09/2015Author
Grant ID
IN-2012-094
EP/K503940/1
EP/K031252/1
EP/K039210/1
Keywords
Metadata
Show full item recordAbstract
Synthesis of 3,4-disubstituted and fused 1,2,5-selenadiazolo[3,4-b]pyrazines via previously unknown 3,4-diamino-1,2,5-selenadiazole has been achieved in moderate to high yields. The compounds synthesized were characterized by elemental analysis, MS and multinuclear (1H, 13C and 77Se) NMR, and the structures of 3,4-diamino-1,2,5-selenadiazole, 5,6-dimethyl[1,2,5]selenadiazolo[3,4-b]pyrazine and 5-phenyl[1,2,5]selenadiazolo[3,4-b]pyrazine were confirmed by X-ray diffraction. Electrochemical reduction of 5,6-R2-1,2,5-selenadiazolo[3,4-b]pyrazines (R = Me, Ph) into persistent radical anions (RAs) was studied by cyclic voltammetry and the RAs were characterized by EPR spectroscopy combined with DFT calculations
Citation
Konstantinova , L S , Bobkova , I E , Nelyubina , Y V , Chulanova , E A , Irtegova , I G , Vasilieva , N V , Sanz Camacho , P , Ashbrook , S E , Hua , G , Slawin , A M Z , Woollins , J D , Zibarev , A V & Rakitin , O A 2015 , ' 1,2,5-Selenadiazolo[3,4-b]pyrazines : synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions ' , European Journal of Organic Chemistry , vol. 2015 , no. 25 , pp. 5585-5593 . https://doi.org/10.1002/ejoc.201500742
Publication
European Journal of Organic Chemistry
Status
Peer reviewed
ISSN
1434-193XType
Journal article
Rights
Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Konstantinova, L. S., Bobkova, I. E., Nelyubina, Y. V., Chulanova, E. A., Irtegova, I. G., Vasilieva, N. V., Camacho, P. S., Ashbrook, S. E., Hua, G., Slawin, A. M. Z., Woollins, J. D., Zibarev, A. V. and Rakitin, O. A. (2015), [1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions. Eur. J. Org. Chem., which has been published in final form at http://dx.doi.org/10.1002/ejoc.201500742 Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Konstantinova, L. S., Bobkova, I. E., Nelyubina, Y. V., Chulanova, E. A., Irtegova, I. G., Vasilieva, N. V., Camacho, P. S., Ashbrook, S. E., Hua, G., Slawin, A. M. Z., Woollins, J. D., Zibarev, A. V. and Rakitin, O. A. (2015), [1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions. Eur. J. Org. Chem., which has been published in final form at http://dx.doi.org/10.1002/ejoc.201500742
Description
The authors acknowledge financial support from the Russian Foundation for Basic Research (Project 13-03-00072), the Presidium of the Russian Academy of Sciences (Programme No.8, Project 8.14) and the Leverhulme Trust (Project IN-2012-094). I.G.I, N.V.V., E.A.C. and A.V.Z. are grateful to the Ministry of Education and Science of the Russian Federation (Project of Joint Laboratories of Siberian Branch of the Russian Academy of Sciences and National Research Universities), and E.A.C. to the BP Company for postgraduate scholarship.Collections
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