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[1,2,5]Selenadiazolo[3,4‐ b ]pyrazines: Synthesis from 3,4‐Diamino‐1,2,5‐selenadiazole and Generation of Persistent Radical Anions
Author(s) -
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.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500742
Subject(s) - chemistry , cyclic voltammetry , electrochemistry , hydrolysis , electron paramagnetic resonance , medicinal chemistry , solid state , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , electrode , physics , nuclear magnetic resonance
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 77 Se 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.