K2CO3-Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage

Ryan A.S. Pike, Rishi R. Sapkota, Bijay Shrestha, Roshan K. Dhungana, Shekhar Kc, Diane A. Dickie, Ramesh Giri

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We describe a novel method to synthesize 2,5-dialkyl-4,6,7-tricyanoindole derivatives from a base-catalyzed reaction of 1,3-diketones with fumaronitrile. The reaction proceeds by the condensation of two molecules of fumaronitrile and one molecule of 1,3-diketone in a remarkable process that involves the cleavage of one C(sp3)-C(sp2) bond in 1,3-diketones and the formation of one carbon-nitrogen bond and four carbon-carbon bonds to construct both the aryl and pyrrole rings of the indole in one step.

Original languageEnglish (US)
Pages (from-to)3268-3272
Number of pages5
JournalOrganic Letters
Volume22
Issue number8
DOIs
StatePublished - Apr 17 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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