[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 Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2015, Volume: 2015, Number: 25, Pages: 5585-5593 Pages count : DOI: 10.1002/ejoc.201500742

Tags

Synthetic methods; Selenium heterocycles; Nitrogen heterocycles; Radical anions; Cyclovoltammetry; EPR spectroscopy; DFT calculations

Authors

Konstantinova Lidia S. ¹ , Bobkova Irina E. ¹ , Nelyubina Yulia V. ² , Chulanova Elena A. ^3,4 , Irtegova Irina G. ³ , Vasilieva Nadezhda V. ³ , Camacho Paula S. ⁵ , Ashbrook Sharon E. ⁵ , Hua Guoxiong ⁵ , Slawin Alexandra M. Z. ⁵ , Woollins J. Derek ⁵ , Zibarev Andrey V. ^3,6,7 , Rakitin Oleg A. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
2	(Данные Web of science) Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
3	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia
4	(Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia
5	(Данные Web of science) Univ St Andrews, Sch Chem, EaStChem, St Andrews KY16 9ST, Fife, Scotland
6	(Данные Web of science) Novosibirsk State Univ, Dept Phys, Novosibirsk 630090, Russia
7	(Данные Web of science) Tomsk State Univ, Dept Chem, Tomsk 634050, Russia

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 Se-77 NMR, and 6, 5-Ph and 5,6-Me-2[1,2,5]selenadiazolo[3,4-b]pyrazines (5a, g, respectively) by X-ray diffraction. Electrochemical reduction of 5,6-R-2[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.

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. , Rakitin O.A.
[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. V.2015. N25. P.5585-5593. DOI: 10.1002/ejoc.201500742 WOS Scopus РИНЦ

Full text from publisher

Published online:	Jul 23, 2015
Published print:	Sep 1, 2015

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