Synthesis 2012; 44(13): 1997-2004
DOI: 10.1055/s-0031-1291135
paper
© Georg Thieme Verlag Stuttgart · New York

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

Authors

  • Maiara T. Saraiva

    a   LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil
  • Natália Seus

    a   LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil
  • Diego de Souza

    b   Labselen-NanoBio, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil, eMail: rodriguesoed@smail.ufsm.br
  • Oscar E. D. Rodrigues*

    b   Labselen-NanoBio, Universidade Federal de Santa Maria, 97105-900 Santa Maria, RS, Brazil, eMail: rodriguesoed@smail.ufsm.br
  • Márcio W. Paixão

    c   Laboratório 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

    a   LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil
  • Eder J. Lenardão

    a   LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil
  • Gelson Perin

    a   LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil
  • Diego Alves*

    a   LASOL, CCQFA, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil
Weitere Informationen

Publikationsverlauf

Received: 21. Dezember 2011

Accepted after revision: 16. April 2012

Publikationsdatum:
25. Mai 2012 (online)


Graphical Abstract

Preview

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.

Supporting Information