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, BrazilRead the publication that featured this abstract
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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