Synthesis of selenium-triazole-carbonitriles by organocatalytic cycloaddition of azidophenyl arylselenides with benzoyl nitriles.

Synthesis of selenium-triazole-carbonitriles by organocatalytic cycloaddition of azidophenyl arylselenides with benzoyl nitriles.

Seus, Natália; Sacramento, Manoela do; Savegnago, Lucielli; Alves, Diego

Abstract:

Nitrogen-containing selenides or diselenides in their structure are a special class of compounds and they have been employed in various organic transformations, for instance, asymmetric synthesis. Consequently, the search of new and efficient methods synthetic, remains a challenge in organic chemistry. In this context, selenium-containing 1,2,3-triazole compounds, are an interesting class of molecules and have a larger synthetic importance since they combine the well known activity of the 1,2,3-triazole core with that of the selenium containing group. Other class of compounds widely explored are the nitriles, which are important synthetic intermediates used in the synthesis of pharmaceuticals, agrochemicals, pigments and as precursors in various transformations of groups of other features. Furthermore, the nitrile group is a unit found in natural products and bioactive molecules. Recently, our research group described the β- enaminone-azide cycloaddition for the synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by reaction of azidophenyl arylselenides with β-ketoesters. Thus, our continuing interest in organocatalytic cicloadditions for the synthesis of functionalized arylselanyl-1,2,3-triazoles, prompted us to extend our protocol for the synthesis of nitrilecontaining triazoles.

Nitrogen-containing selenides or diselenides in their structure are a special class of compounds and they have been employed in various organic transformations, for instance, asymmetric synthesis. Consequently, the search of new and efficient methods synthetic, remains a challenge in organic chemistry. In this context, selenium-containing 1,2,3-triazole compounds, are an interesting class of molecules and have a larger synthetic importance since they combine the well known activity of the 1,2,3-triazole core with that of the selenium containing group. Other class of compounds widely explored are the nitriles, which are important synthetic intermediates used in the synthesis of pharmaceuticals, agrochemicals, pigments and as precursors in various transformations of groups of other features. Furthermore, the nitrile group is a unit found in natural products and bioactive molecules. Recently, our research group described the β- enaminone-azide cycloaddition for the synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by reaction of azidophenyl arylselenides with β-ketoesters. Thus, our continuing interest in organocatalytic cicloadditions for the synthesis of functionalized arylselanyl-1,2,3-triazoles, prompted us to extend our protocol for the synthesis of nitrilecontaining triazoles.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20131014163026

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Como citar:

Seus, Natália; Sacramento, Manoela do; Savegnago, Lucielli; Alves, Diego; "Synthesis of selenium-triazole-carbonitriles by organocatalytic cycloaddition of azidophenyl arylselenides with benzoyl nitriles.", p-306-306. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20131014163026