Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-a]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile.

Loana I Monzon, Nicole C M Rocha, Gabriela T Quadros, Pâmela P P Nunes, Roberta Cargnelutti, Raquel G Jacob, Eder J Lenardão, Gelson Perin, Daniela Hartwig

Molecules (Basel, Switzerland) 2023 Jun 27

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A general methodology to access valuable 4-(phenylchalcogenyl)tetrazolo[1,5-a]quinolines was developed by the reaction of 2-azidobenzaldehyde with phenylchalcogenylacetonitriles (sulfur and selenium) in the presence of potassium carbonate (20 mol%) as a catalyst. The reactions were conducted using a mixture of dimethylsulfoxide and water (7:3) as solvent at 80 °C for 4 h. This new methodology presents a good functional group tolerance to electron-deficient and electron-rich substituents, affording a total of twelve different 4-(phenylchalcogenyl)tetrazolo[1,5-a]quinolines selectively in moderate to excellent yields. The structure of the synthesized 4-(phenylselanyl)tetrazolo[1,5-a]quinoline was confirmed by X-ray analysis.

Citation

Loana I Monzon, Nicole C M Rocha, Gabriela T Quadros, Pâmela P P Nunes, Roberta Cargnelutti, Raquel G Jacob, Eder J Lenardão, Gelson Perin, Daniela Hartwig. Synthesis of 4-(Phenylchalcogenyl)tetrazolo[1,5-a]quinolines by Bicyclization of 2-Azidobenzaldehydes with Phenylchalcogenylacetonitrile. Molecules (Basel, Switzerland). 2023 Jun 27;28(13)