Synlett 2012; 23(7): 1052-1056
DOI: 10.1055/s-0031-1290770
letter
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Polysubstituted N2-Alkyl/Aryl-1,2,3-Triazoles via 4-Bromo-5-iodo-1,2,3-triazole

Authors

  • Li Zhang*

    Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, CT 06877, USA, Fax: +1(203)7916130   Email: li.zhang@boehringer-ingelheim.com
  • Zhibin Li

    Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, CT 06877, USA, Fax: +1(203)7916130   Email: li.zhang@boehringer-ingelheim.com
  • Xiao-jun Wang

    Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, CT 06877, USA, Fax: +1(203)7916130   Email: li.zhang@boehringer-ingelheim.com
  • Nathan Yee

    Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, CT 06877, USA, Fax: +1(203)7916130   Email: li.zhang@boehringer-ingelheim.com
  • Chris H. Senanayake

    Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield, CT 06877, USA, Fax: +1(203)7916130   Email: li.zhang@boehringer-ingelheim.com
Further Information

Publication History

Received: 11 January 2012

Accepted after revision: 22 February 2012

Publication Date:
05 April 2012 (online)


Graphical Abstract

Abstract

The regioselective N2-substitution of 4-bromo-5-iodo-1,2,3-triazole with alkyl/aryl halides in the presence of K2CO3 in DMF produced the desired 2-substituted 4-bromo-5-iodo-1,2,3-triazoles as a major products in good to excellent regioselectivity. Subsequent chemoselective Suzuki–Miyaura cross-coupling reaction of N2-substituted 4-bromo-5-iodo-1,2,3-triazoles provided polysubstituted 1,2,3-triazoles efficiently.

Supporting Information