This article is cited in 8 papers

Communications

First synthesis of new polycyclic systems from ortho-di(heteroaryl)-substituted furazanopyrazine derivatives by the Scholl reaction

E. V. Verbitskiy^ab, Yu. A. Kvashnin^ab, M. V. Medvedeva^b, T. S. Svalova^b, A. N. Kozitsina^b, O. S. Eltsov^b, G. L. Rusinov^ab, V. N. Charushin<sup>ab

a</sup> I.Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Institute of Chemical Engineering, Ural Federal University, Ekaterinburg, Russian Federation

Abstract: A facile synthetic protocol to hard-to-get polycyclic (hetero)-aromatic compounds annulated to [1,2,4]oxadiazolo[3,4-b]-pyrazine scaffold via the FeCl₃-mediated intramolecular Scholl cross-coupling has been developed. Based on the electrochemical and photophysical measurements, the synthesized polycyclic systems may be regarded as narrow band-gap (from 1.42 to 1.89 eV) n-type organic semiconductors whose energy levels are comparable to those of the commercially available n-type semiconductors

Keywords: furazanopyrazines, Scholl reaction, organic semiconductors, C–H functionalization, S^H-reaction, polycyclic aromatic, hydrocarbons, iron trichloride.

Language: English

DOI: 10.1016/j.mencom.2022.11.005

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