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

Валерий O. Филимонов, Владимир Т. Абаев, Татьяна В. Березкина, Кристина A. Галата, Павел A. Слепухин, Мария А. Костенко, Вера С. Берсенева
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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*


Keywords


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

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