Abstract

An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.

Original languageEnglish
Pages (from-to)11232-11244
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number18
DOIs
Publication statusPublished - 21 Sep 2018

Scopus subject areas

  • Organic Chemistry

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