Microwave-enhanced efficient regioselective synthesis of 1,3,4-trisubstituted 2-mercaptoimidazoles on a soluble support

Gorakh S. Yellol, Cheng Ting Chou, Wang Jin Chang, Barnali Maiti, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

A novel efficient synthetic method for regioselective synthesis of optically active 2-mercapto-imidazoles with three points of structural diversity was investigated on a polyethylene glycol (PEG) support. The key synthetic steps involve (i) synthesis of thiourea derivatives of polymer-supported amino acids with isothiocyanates and (ii) one-pot regioselective condensation of PEG-linked thiourea with abromo ketones to furnish the 2-mercaptoimidazole skeleton under microwave conditions. An excellent regioselectivity was observed during this one-pot condensation reaction which was further supported by NOE studies. In addition to three sets of structural diversity, supplementary chirality at the a-position of the 2-mercaptoimidazole skeleton is the key feature of this synthesis. A representative set of 2-mercaptoimidazoles was efficiently assembled on soluble support utilizing various l-amino acids, isothiocyanates and a-bromoaryl ketones with good yields.

Original languageEnglish
Pages (from-to)187-196
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number1
DOIs
StatePublished - 1 Jan 2012

Keywords

  • Mercaptoimidazoles
  • Microwave chemistry
  • Nitrogen heterocycles
  • Polyethylene glycol
  • Soluble supported synthesis

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