SYNTHESIS OF DITHIENOQUINAZOLINES FROM PYRIMIDINES <i>via</i> INTRAMOLECULAR NUCLEOPHILIC AROMATIC SUBSTITUTION OF HYDROGEN

Authors

  • Егор В. Вербицкий Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoy / 20 Akademicheskaya St., Yekaterinburg 620219
  • Екатерина Династия Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoy / 20 Akademicheskaya St., Yekaterinburg 620219
  • Анна Баранова Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Олег Ельцов Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Геннадий Русинов Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoy / 20 Akademicheskaya St., Yekaterinburg 620219
  • Олег Николаевич Чупахин Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoy / 20 Akademicheskaya St., Yekaterinburg 620219
  • Валерий Николаевич Чарушин Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoy / 20 Akademicheskaya St., Yekaterinburg 620219

DOI:

https://doi.org/10.1007/4037

Keywords:

pyrimidines, quinazolines, thienocenes, nucleophilic aromatic substitution of hydrogen

Abstract

The possibility of intramolecular nucleophilic aromatic substitution of hydrogen in the series of 5-[2-(het)aryl-1-benzothiophen-3-yl]pyrimidines was explored. A convenient method for the synthesis of [1]benzothieno[3,2-f]thieno[2,3-h]quinazoline and [1]benzothieno[3,2-f]thieno[3,2-h]quinazoline based on the developed SNH protocol was proposed. The energy parameters (width of the band gap, the energy of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbitals (LUMO)) of benzothieno[3,2-f]thieno[2,3-h]quinazoline synthesized for the first time were determined based on the data of the absorption spectra and cyclic voltammetry.

Authors: Egor V. Verbitskiy*, Ekaterina M. Dinastiya, Anna A. Baranova, Oleg S. Eltsov, Gennady L. Rusinov, Oleg N. Chupakhin, Valery N. Charushin

Author Biography

Егор В. Вербицкий, Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoy / 20 Akademicheskaya St., Yekaterinburg 620219

Старший научный сотрудник лаборатории гетероциклических соединений

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Published

2017-11-29

Issue

Vol. 53 No. 10 (2017)

Section

Original Papers