Morita-Baylis-Hillman Reaction with 7-Chloroquinoline Derivatives‑New Compounds with Potential Anticancer Activity

Oliveira, João Paulo Gomes de; Caleffi, Guilherme S.; Silva, Everton P.; Coelho, Maísa Cavalcanti; Castro, Aleff Cruz de; Mendes, Rhuan Karlos Santos; Olegário, Tayná Rodrigues; Lima-Júnior, Cláudio Gabriel; Vasconcellos, Mário L. A. A.; Souza, Júlia L. C.; Souza, Silvia M. de; Militão, Gardênia Carmen Gadelha; Vaz, Boniek G.; Ramalho, Ruver Rodrigues Feitosa

doi:10.21577/0103-5053.20200185

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2021

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“…Synthetic studies were conducted using a Vapourtec E-series system equipped with three peristaltic pumps, T- or Y-mixers, and coil reactors (3 mL). First, aiming to determine the best conditions for the functionalization of 4,7-dichoroquinoline ( 18 ), which is an important drug intermediate, − we pumped anhydrous solutions of this substrate and TMPMgCl·LiCl (1.1–2 equiv) in THF with the in-flow-generated organomagnesium intermediate 22 being dispensed into an iodine stock solution as a batch quench (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2021

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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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Section: Resultsmentioning

confidence: 99%