A regioselective [4 + 2] annulation approach to 5-acylindolizine-7-carbonitriles: generation of poly-substituted pyridines

Sunmi Kim, Jeong Hwa Lee, Seok Hyun Yoon, Ikyon Kim

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

The reaction of β-ketonitrile andN-substituted pyrrole-2-carboxaldehyde in the presence of piperidinium acetate in CH3CN permitted regioselective access to 5-acylindolizine-7-carbonitrile through a domino Knoevenagel condensation-intramolecular aldol cyclization sequence. A wide range of new indolizine derivatives with a poly-functionalized pyridine moiety were readily synthesized in an atom-economical fashion, thereby expanding the indolizine chemical space for further applications.

Original languageEnglish
Pages (from-to)5806-5817
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume19
Issue number26
DOIs
Publication statusPublished - 2021 Jul 14

Bibliographical note

Funding Information:
We thank the National Research Foundation of Korea (NRF-2018R1A6A1A03023718 and NRF-2020R1A2C2005961) for generous financial support.

Publisher Copyright:
© The Royal Society of Chemistry 2021.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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