Polycyclic N-heterocyclic compounds. Part 631 improved synthesis of 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines via truce-smiles rearrangement and subsequent formation to furo[2,3-c]isoquinoline

Kensuke Okuda, Masahiko Yoshida, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

An improved synthesis of 5-amino-1,2-dihydrofuro[2,3-c]isoquinoline has been achieved using a slight modification of reaction conditions for the Truce-Smiles rearrangement. Acid treatment of the obtained 5-amino-1,2- dihydrofuro[2,3-c]isoquinolines gave unexpected ring-opened spiro ring compounds. The previously unreported parent compound, furo[2,3-c]isoquinoline, was also synthesized.

Original languageEnglish
Pages (from-to)363-368
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume58
Issue number3
DOIs
Publication statusPublished - Mar 2010

Keywords

  • Furo[2,3-b]pyridine
  • Furo[2,3-c]isoquinoline
  • Heterocycle
  • Spiro[cyclopropane-(1,4′)-isoquinoline]
  • Truce-smiles rearrangement

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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