Novel methods for the synthesis of heterocycles using highly reactive spirocyclopropanes

Hisanori Nambu*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

1 Scopus citations

Abstract

This review describes our recent efforts to develop efficient methods for the synthesis of heterocyclic compounds, such as indoles and benzofurans, employing ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes, which were prepared by the reaction of 1,3-cyclohexanediones with sulfonium salts. Ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with primary amines proceeded at room temperature to provide 2-substituted tetrahydroindol-4(5H)-ones in good to excellent yield. The obtained product was readily converted into a 2-substituted 4-hydroxyindole derivative. Furthermore, acid-catalyzed ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes proceeded smoothly at room temperature to provide 2-substituted tetrahydrobenzofuran-4(2H)-ones in excellent yield. The obtained product was converted into a 2-substituted 4-hydroxybenzofuran derivative. The synthetic utility of this catalytic protocol was demonstrated by the total synthesis of cuspidan B.

Original languageEnglish
Pages (from-to)19-25
Number of pages7
JournalYakugaku Zasshi
Volume138
Issue number1
DOIs
StatePublished - 2018

Keywords

  • Benzofuran
  • Cyclization
  • Indole
  • Ring-opening
  • Spirocyclopropane
  • Sulfonium salt

ASJC Scopus subject areas

  • Pharmacology
  • Pharmaceutical Science

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