Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents

    • Valter E. Muriea
    • Paula V. Nicolinoa
    • Thiago dos Santosa
    • Guido Gambacortab
    • Rodolfo H. V. Nishimuraa
    • Icaro S. Perovanic
    • Luciana C. Furtadod
    • Leticia V. Costa-Lotufod
    • Anderson Moraes de Oliveirac
    • Ricardo Vessecchic
    • Ian R. Baxendaleb
    • Giuliano C. Clososkib, c
    • aDepartamento de Ciências BioMoleculares, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Av. do Café S/N, Ribeirão Preto 14040-903, Brazil
    • bDepartment of Chemistry, Durham University, South Road, Durham DH1 3LE, United Kingdom
    • cDepartamento de Química, Faculdade de Filosofia Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes 3900, Ribeirão Preto 14040-901, Brazil
    • dDepartamento de Farmacologia, Instituto de Ciências Biomédicas, Universidade de São Paulo, Av. Prof. Lineu Prestes 1524, São Paulo 05508-900, Brazil

    We have prepared a library of functionalized quinolines through the magnesiation of 7-chloroquinolines under mild conditions, employing both batch and continuous flow conditions. The preparation involved the generation of mixed lithium-magnesium intermediates, which were reacted with different electrophiles. Mixed lithium-zinc reagents allowed the synthesis of halogenated and arylated derivatives. Some of the synthesized 4-carbinol quinolines have shown interesting antiproliferative properties, their hydroxyl group being a suitable amino group bioisostere. We also report a two-step approach for optically active derivatives.

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