One-pot synthesis of polycyclic heterocyclic compounds by condensation of 1-carbamoylmethyl-2,3,3-trimethyl-3H-indolium salts with pyridine-2, 3, and 4-and quinoline-4-carboxaldehydes

Algirdas Sackus (Corresponding author), Zivile Zukauskaite, Neringa Kleiziene, Aurimas Bieliauskas, Virgine Amankaviciene, Wolfgang Holzer, Vytas Martynaitis

    Publications: Contribution to journalArticlePeer Reviewed

    Abstract

    A simple and efficient method was developed for the synthesis of 2,​6-​dihydropyrano[2,​3-​c]​pyrazoles I [R = H, F, Br] via ring-​closing metathesis (RCM) of 4-​ethenyl-​1-​aryl-​3-​[(prop-​2-​en-​1-​yl)​oxy]​-​1H-​pyrazoles II using Grubbs' first generation catalyst. The required diene substrates II for the RCM reaction were prepd. by a three-​step procedure starting from 1-​aryl-​1H-​pyrazol-​3-​ols. The structures of the obtained heterocyclic products were unequivocally confirmed by detailed 1H, 13C, 15N and 19F NMR spectroscopic expts. and HRMS measurements. The optical properties of compd. I [R = H] were studied by UV-​Vis and fluorescence spectroscopy.
    Original languageEnglish
    Pages (from-to)3679-3690
    Number of pages12
    JournalTetrahedron
    Volume74
    Issue number27
    DOIs
    Publication statusPublished - 5 Jul 2018

    Austrian Fields of Science 2012

    • 104015 Organic chemistry

    Keywords

    • One-pot synthesis
    • Pyridine
    • Quinoline
    • Indole
    • Indolizine
    • Imidazo[1,2-a]indole
    • Pyrrolo[1,2-a]indole
    • MULTICOMPONENT SYNTHESES
    • AROMATIC-ALDEHYDES
    • CRYSTAL-STRUCTURES
    • DERIVATIVES
    • 1-(2-PYRIDYL)-2-PROPEN-1-OL
    • REARRANGEMENT
    • INDOLIZINES
    • CYCLIZATION
    • CHEMISTRY
    • CHLORIDE

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