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

Lidia S. Konstantinova; Irina E. Bobkova; Yulia V. Nelyubina; Elena A. Chulanova; Irina G. Irtegova; Nadezhda V. Vasilieva; Paula Sanz Camacho; Sharon Elizabeth  Ashbrook; Guoxiong Hua; Alexandra Martha Zoya Slawin; J Derek Woollins; Andrey V. Zibarev; Oleg A. Rakitin

doi:10.1002/ejoc.201500742

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

Lidia S. Konstantinova, Irina E. Bobkova, Yulia V. Nelyubina, Elena A. Chulanova, Irina G. Irtegova, Nadezhda V. Vasilieva, Paula Sanz Camacho, Sharon Elizabeth Ashbrook, Guoxiong Hua, Alexandra Martha Zoya Slawin, J Derek Woollins, Andrey V. Zibarev, Oleg A. Rakitin

Research output: Contribution to journal › Article › peer-review

Abstract

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

Original language	English
Pages (from-to)	5585-5593
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	25
Early online date	23 Jul 2015
DOIs	https://doi.org/10.1002/ejoc.201500742
Publication status	Published - Sept 2015

Keywords

Synthesis
[1,2,5]selenadiazolo[3,4-b]pyrazines
α- diketones
3,4-diamino-1,2,5-selenadiazole
Cyclic voltammetry
EPR spectroscopy
DFT calculations
X-ray diffraction

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10.1002/ejoc.201500742

Woollins_2015_EJOC_1,2,5_AM
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
Accepted author manuscript, 1.17 MB
Woollins_2015_EJOC_1,2,5_AM-Supp
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
Accepted author manuscript, 1.41 MB

Cite this

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, 2015(25), 5585-5593. https://doi.org/10.1002/ejoc.201500742

@article{43566c54c4c94dcfb7ba110c3f67fc45,

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

abstract = "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",

keywords = "Synthesis, [1,2,5]selenadiazolo[3,4-b]pyrazines, α- diketones, 3,4-diamino-1,2,5-selenadiazole, Cyclic voltammetry, EPR spectroscopy, DFT calculations, X-ray diffraction",

author = "Konstantinova, {Lidia S.} and Bobkova, {Irina E.} and Nelyubina, {Yulia V.} and Chulanova, {Elena A.} and Irtegova, {Irina G.} and Vasilieva, {Nadezhda V.} and {Sanz Camacho}, Paula and Ashbrook, {Sharon Elizabeth} and Guoxiong Hua and Slawin, {Alexandra Martha Zoya} and Woollins, {J Derek} and Zibarev, {Andrey V.} and Rakitin, {Oleg A.}",

note = "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. ",

year = "2015",

month = sep,

doi = "10.1002/ejoc.201500742",

language = "English",

volume = "2015",

pages = "5585--5593",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "25",

}

Konstantinova, LS, Bobkova, IE, Nelyubina, YV, Chulanova, EA, Irtegova, IG, Vasilieva, NV, Sanz Camacho, P, Ashbrook, SE, Hua, G, Slawin, AMZ, Woollins, JD, Zibarev, AV & Rakitin, OA 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

TY - JOUR

T1 - 1,2,5-Selenadiazolo[3,4-b]pyrazines

T2 - synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions

AU - Konstantinova, Lidia S.

AU - Bobkova, Irina E.

AU - Nelyubina, Yulia V.

AU - Chulanova, Elena A.

AU - Irtegova, Irina G.

AU - Vasilieva, Nadezhda V.

AU - Sanz Camacho, Paula

AU - Ashbrook, Sharon Elizabeth

AU - Hua, Guoxiong

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, J Derek

AU - Zibarev, Andrey V.

AU - Rakitin, Oleg A.

N1 - 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.

PY - 2015/9

Y1 - 2015/9

N2 - 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

AB - 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

KW - Synthesis

KW - [1,2,5]selenadiazolo[3,4-b]pyrazines

KW - α- diketones

KW - 3,4-diamino-1,2,5-selenadiazole

KW - Cyclic voltammetry

KW - EPR spectroscopy

KW - DFT calculations

KW - X-ray diffraction

UR - http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500742/suppinfo

U2 - 10.1002/ejoc.201500742

DO - 10.1002/ejoc.201500742

M3 - Article

SN - 1434-193X

VL - 2015

SP - 5585

EP - 5593

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

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

Abstract

Keywords

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