Cycloisomerization of Oxindole-Derived 1,5-Enynes: A Calcium(II)-Catalyzed One-Pot, Solvent-free Synthesis of Phenanthridinones, 3-(Cyclopentenylidene)indolin-2-ones and 3-Spirocyclic Indolin-2-ones

Srinivasarao Yaragorla, Abhishek Pareek, Ravikrishna Dada

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

Calcium-catalyzed regioselective synthesis of oxindole-derived 1,5-enynes, followed by cycloisomerization, from readily accessible 3-hydroxy-3-(alkynyl)indolin-2-ones and styrenes in one-pot, under solvent-free conditions is described. This method offers the synthesis of diverse molecules: phenanthridinones, 3-(cyclopentenylidene)indolin-2-ones, and 3-spirocyclic indolin-2-ones are obtained through cascade reactions including cross-dehydrative-coupling, [3,3]-sigmatropic rearrangement, carbocyclization, isomerization, oxidative-ring rearrangement, and Diels-Alder cycloaddition. In addition, this method features atom- and step-economy, broad substrate scope, and high yields. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)3068-3075
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number17
DOIs
StatePublished - Sep 4 2017
Externally publishedYes

Bibliographical note

Funding Information:
This work is partially supported by SERB (SB/FT/CS-149/2012) and CSIR (02/200/14/EMR-II) India. AP and RD thank Central University of Rajasthan for the fellowships. Authors are grateful to Dr. Gopal K and Mr. Sudhir M for the technical support in solving the crystal structures.

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • 1,5-enynes
  • Diels-Alder reaction
  • calcium catalysis
  • cycloisomerization
  • phenanthridinones
  • regioselective

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