Cyanoquinolines and furo[3,4‑b]quinolinones formation via on-the-spot 2,3-functionalization of quinolines with cyanopropargylic alcohols

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Опубликована статья: Belyaeva K.V., Nikitina L.P., Afonin A.V., Grishchenko L.A., Trofimov B.A. Cyanoquinolines and furo[3,4‑b]quinolinones formation via on-the-spot 2,3-functionalization of quinolines with cyanopropargylic alcohols // Journal of Organic Chemistry. – 2021. – V. 86. – Iss. 5. – P. 3800-3809. IF 4,354. Q1 (БАЦКП, РФФИ 18-03-00762-a). 19.02.2021. DOI: 10.1021/acs.joc.0c02644

Abstract: A convenient approach to 2-(1-ethoxyalkoxy)-3-cyanoquinolines (in up to 50% yields) has been developed. The approach comprises functionalization of quinolines with acetals of cyanopropargylic alcohols (KOH/H2O/MeCN, 55–60 °C) followed by their transformation to furo[3,4-b]quinolinones (in up to 98% yields) via the sequential removal of acetal protection and intramolecular cyclization/hydration (7% aqueous HCl, acetone, 20–25 °C).

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