Polycyclic N-heterocyclic compounds. Part 61: A novel Truce-Smiles type rearrangement reaction of 4-(2-cyanovinyloxy)butanenitriles to give cycloalkeno[1,2-d]furo[2,3-b]pyridines

Kensuke Okuda, Norimasa Watanabe, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The cycloalkeno[1,2-d]furo[2,3-b]pyridine skeleton was conveniently synthesized from fused 4-(2-cyanovinyloxy)butanenitriles in one step through sequential intramolecular Michael addition, β-elimination and intramolecular nucleophilic addition. This sequence thus consists of a novel Truce-Smiles type rearrangement followed by cyclization. The 5-amino derivatives were transformed further to lactams in good yields.

Original languageEnglish
Pages (from-to)903-906
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number6
DOIs
Publication statusPublished - Feb 10 2010

Keywords

  • Cyanovinyl ether
  • Cycloalkeno[1,2-d]furo[2,3-b]pyridine
  • Estervinyl ether
  • Heterocycle
  • Michael addition
  • Truce-Smiles rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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