Synthesis of [(Arylselanyl)alkyl]-1,2,3-triazoles by Copper-Catalyzed 1,3-Dipolar Cycloaddition of (Arylselanyl)alkynes with Benzyl Azides

Maiara T. Saraiva; Natália Seus; Diego de Souza; Oscar E. D. Rodrigues; Márcio W. Paixão; Raquel G. Jacob; Eder J. Lenardão; Gelson Perin; Diego Alves

doi:10.1055/s-0031-1291135

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(13): 1997-2004
DOI: 10.1055/s-0031-1291135

paper

Synthesis of [(Arylselanyl)alkyl]-1,2,3-triazoles by Copper-Catalyzed 1,3-Dipolar Cycloaddition of (Arylselanyl)alkynes with Benzyl Azides

Maiara T. Saraiva

^aLASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil

,

Natália Seus

^aLASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil

,

Diego de Souza

^bLabselen-NanoBio, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil, eMail: rodriguesoed@smail.ufsm.br

,

Oscar E. D. Rodrigues*

^bLabselen-NanoBio, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil, eMail: rodriguesoed@smail.ufsm.br

,

Márcio W. Paixão

^cLaboratório de Síntese de Produtos Naturais, Universidade Federal de São Carlos, São Carlos, SP, Brazil, Fax: +55(53)32757533 eMail: diego.alves@ufpel.edu.br

,

Raquel G. Jacob

^aLASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil

,

Eder J. Lenardão

^aLASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil

,

Gelson Perin

^aLASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil

,

Diego Alves*

^aLASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil

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Abstract

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Abstract

In the presence of catalytic amounts of copper salts and sodium ascorbate, various (arylselanyl)alkynes underwent click-type 1,3-dipolar cycloaddition reactions with a range of benzyl azides bearing electron-withdrawing or electron-donating groups to give a series of novel [(arylselanyl)alkyl]-1,2,3-triazoles. This click chemistry protocol is an efficient method for synthesizing new selenium–nitrogen compounds that are potentially useful in biological studies.

Key words

heterocycles - azides - alkynes - click reactions - selenium - cycloadditions - catalysis - copper

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Referenzen

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