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

    25 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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