An Expeditious Benzannulation Reaction of Indol-3-yl-but-3-yn-2-ols to Substituted 2-Iodocarbazoles via Domino 5-endo Spirocyclization/Selective Vinyl Shift and Aromatization

Srinivasarao Yaragorla, Ravikrishna Dada, Debojyoti Bag

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

Regioselective benzannulation reaction of indol-3-yl-but-3-yn-2-ols to functionaly embellished 2-iodocarbazoles is described for the first time using iodine at room temperature in an open flask. This reaction proceeds through a cascade of 5-endo spirocyclization, ring-rearrangement through a vinyl shift, and aromatization in a short time. This protocol offers direct access to uncovered 2-iodocarbazoles, with a broad substrate scope and good to moderate yields. Further, we have demonstrated the synthetic potential of these compounds using cross-coupling reactions.

Original languageEnglish (US)
Pages (from-to)6983-6988
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number41
DOIs
StatePublished - Nov 10 2019
Externally publishedYes

Bibliographical note

Funding Information:
S. Y. is thankful for the financial support from CSIR (02/333/18/EMR‐II) India and SERB‐2016/4812. R. D. is thankful to SERB for the fellowship. We also acknowledge Dr Jovan Jose for his support for elucidating the mechanism.

Publisher Copyright:
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • 2-Iodocarbazoles
  • Benzannulation
  • Cross-coupling
  • Iodocyclization
  • Reaction mechanisms

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