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Cyclizations of The Isothiocyanates-Derived Azatrienes: The CuBr–Catalyzed Switching from Thiophenes to Pyrroles

European Journal of Organic Chemistry, ISSN: 1099-0690, Vol: 2018, Issue: 43, Page: 5961-5971
2018
  • 13
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Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    13
    • Citation Indexes
      13
  • Captures
    2

Article Description

Azatrienes, alkyl 2-alkoxy-N-buta-2,3-dienimidothioates, prepared from isothiocyanates, lithiated alkoxyallenes, and alkyl 2-bromoacetates, readily cyclize in the presence of CuBr to selectively give rare functionalized pyrroles in up to 82 % yield that contrasts with the base-catalyzed cyclization of the same azatrienes affording only thiophenes. This switching becomes possible due to the preisolation of azatrienes and their further contact with CuBr (6–9 mol-%). A synthetically convenient route to so far inaccessible densely functionalized pyrroles has been developed.

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