TANDEM KNOEVENAGEL CONDENSATION AND INTRAMOLECULAR CYCLOADDITION REACTIONS OF 2-AZIDOBENZALDEHYDES WITH 2-CYANOACETAMIDES IN THE SYNTHESIS OF 4-THIOCARBAMOYLTETRAZOLO[1,5-<i>a</i>]QUINOLINES

Authors

  • Валерий O. Филимонов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002
  • Владимир Т. Абаев K. L. Khetagurov North Ossetian State University, 44-46 Vatutin St., Vladikavkaz 362025
  • Татьяна В. Березкина Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002
  • Кристина A. Галата Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002
  • Павел A. Слепухин I. Ya. Postovsky Institute of Organic Synthesis of the Ural Branch of RAS, 20 S. Kovalevskoy St., Ekaterinburg 620990
  • Мария А. Костенко Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002
  • Вера С. Берсенева Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002

DOI:

https://doi.org/10.1007/3374

Keywords:

2-azidobenzaldehydes, tetrazolo[1, 5-а]quinoline, cyanoacetic acid thioamides, structural isomers, cyclocondensation, cycloaddition

Abstract

The reaction of 2-azidobenzaldehydes with 2-thioamides of cyanoacetic acid proceeds without a solvent and presence of a base at 80–90°C selectively by one of the possible routes to form tetrazolo[1,5-a]quinolines. The proposed mechanism of the reaction involves the Knoevenagel condensation and subsequent intramolecular [3+2] cycloaddition of the azide group at the S≡N bond of an intermediate acrylonitrile.

Authors: Valery O. Filimonov, Vladimir T. Abaev, Tatyana V. Berezkina, Kristina A. Galata, Pavel A. Slepukhin, Maria A. Kostenko, Vera S. Berseneva*

Author Biographies

Валерий O. Филимонов, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002

младший научный сотрудник кафедры технологии органического синтеза

Татьяна В. Березкина, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002

с.н.с. кафедры технологии органического синтеза

Кристина A. Галата, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002

м.н.с. кафедры технологии органического синтеза

Мария А. Костенко, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002

студентка

Вера С. Берсенева, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mir St., Yekaterinburg 620002

доцент кафедры Технологии органического синтеза

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Published

2016-10-11

Issue

Vol. 52 No. 9 (2016): Pericyclic reactions in heterocyclic chemistry

Section

Original Papers